Estrone (E1), sold under the brand names Estragyn, Kestrin, and Theelin among many others, is an
estrogen
Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal acti ...
medication and
naturally occurring
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synt ...
steroid hormone
A steroid hormone is a steroid that acts as a hormone. Steroid hormones can be grouped into two classes: corticosteroids (typically made in the adrenal cortex, hence ''cortico-'') and sex steroids (typically made in the gonads or placenta). Wi ...
which has been used in
menopausal hormone therapy
Hormone replacement therapy (HRT), also known as menopausal hormone therapy or postmenopausal hormone therapy, is a form of hormone therapy used to treat symptoms associated with female menopause. These symptoms can include hot flashes, vagina ...
and for other indications.
It has been provided as an
aqueous suspension
In chemistry, a suspension is a Mixture#Homogeneous and heterogeneous mixtures, heterogeneous mixture of a fluid that contains solid particles sufficiently large for sedimentation. The particles may be macroscopic, visible to the naked eye, usual ...
or
oil solution
An oil is any nonpolar chemical substance that is composed primarily of hydrocarbons and is hydrophobic (does not mix with water) & lipophilic (mixes with other oils). Oils are usually flammable and surface active. Most oils are unsaturated ...
given by
injection into muscle
Intramuscular injection, often abbreviated IM, is the injection of a substance into a muscle. In medicine, it is one of several methods for parenteral administration of medications. Intramuscular injection may be preferred because muscles have l ...
and as a
vaginal
In mammals, the vagina is the elastic, muscular part of the female genital tract. In humans, it extends from the vestibule to the cervix. The outer vaginal opening is normally partly covered by a thin layer of mucosal tissue called the hyme ...
cream
Cream is a dairy product composed of the higher-fat layer skimmed from the top of milk before homogenization. In un-homogenized milk, the fat, which is less dense, eventually rises to the top. In the industrial production of cream, this process ...
applied
inside of the vagina.
It can also be taken
by mouth
Oral administration is a route of administration where a substance is taken through the mouth. Per os abbreviated to P.O. is sometimes used as a direction for medication to be taken orally. Many medications are taken orally because they are i ...
as
estradiol/estrone/estriol
Estradiol/estrone/estriol (brand name Hormonin) is a combination pharmaceutical medication produced by Shire which contains the estrogens estradiol (0.3 or 0.6 mg), estrone (0.7 or 1.4 mg), and estriol (0.135 or 0.27 mg) in a singl ...
(brand name Hormonin) and in the form of
prodrug
A prodrug is a medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug ...
s like
estropipate
Estropipate, also known as piperazine estrone sulfate and sold under the brand names Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others, is an estrogen medication which is used mainly in menopausal hormone therapy in the treatment ...
(
estrone sulfate
Estrone sulfate, also known as E1S, E1SO4 and estrone 3-sulfate, is a natural, endogenous steroid and an estrogen ester and conjugate.
In addition to its role as a natural hormone, estrone sulfate is used as a medication, for instance in menop ...
; brand name Ogen) and
conjugated estrogens (mostly estrone sulfate; brand name Premarin).
Side effects of estrogens like estrone include
breast tenderness,
breast enlargement,
headache
Headache is the symptom of pain in the face, head, or neck. It can occur as a migraine, tension-type headache, or cluster headache. There is an increased risk of depression in those with severe headaches.
Headaches can occur as a result ...
,
nausea
Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. While not painful, it can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the ...
,
fluid retention, and
edema
Edema, also spelled oedema, and also known as fluid retention, dropsy, hydropsy and swelling, is the build-up of fluid in the body's Tissue (biology), tissue. Most commonly, the legs or arms are affected. Symptoms may include skin which feels t ...
, among others.
Estrone is a
naturally occurring
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synt ...
and
bioidentical estrogen, or an
agonist
An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...
of the
estrogen receptor, the
biological target of
estrogen
Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal acti ...
s like
endogenous
Endogenous substances and processes are those that originate from within a living system such as an organism, tissue, or cell.
In contrast, exogenous substances and processes are those that originate from outside of an organism.
For example, es ...
estradiol.
It is a relatively weak estrogen, with much lower
activity than
estradiol.
However, estrone is
converted
Conversion or convert may refer to:
Arts, entertainment, and media
* "Conversion" (''Doctor Who'' audio), an episode of the audio drama ''Cyberman''
* "Conversion" (''Stargate Atlantis''), an episode of the television series
* "The Conversion" ...
in the body into estradiol, which provides most or all of its estrogenic
potency
Potency may refer to:
* Potency (pharmacology), a measure of the activity of a drug in a biological system
* Virility
* Cell potency, a measure of the differentiation potential of stem cells
* In homeopathic dilutions, potency is a measure of how ...
.
As such, estrone is a
prodrug
A prodrug is a medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug ...
of estradiol.
Estrone was first discovered in 1929, and was introduced for medical use shortly thereafter.
Although it has been used clinically in the past, estrone has largely been discontinued and is mostly no longer marketed.
Medical uses
Estrone has been marketed in
intramuscular
Intramuscular injection, often abbreviated IM, is the injection of a substance into a muscle. In medicine, it is one of several methods for parenteral administration of medications. Intramuscular injection may be preferred because muscles have l ...
and
vaginal
In mammals, the vagina is the elastic, muscular part of the female genital tract. In humans, it extends from the vestibule to the cervix. The outer vaginal opening is normally partly covered by a thin layer of mucosal tissue called the hyme ...
formulations and was used as an
estrogen
Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal acti ...
in the treatment of
symptom
Signs and symptoms are the observed or detectable signs, and experienced symptoms of an illness, injury, or condition. A sign for example may be a higher or lower temperature than normal, raised or lowered blood pressure or an abnormality showin ...
s of
low estrogen levels such as
hot flash
Hot flashes (also known as hot flushes) are a form of flushing, often caused by the changing hormone levels that are characteristic of menopause. They are typically experienced as a feeling of intense heat with sweating and rapid heartbeat, and ...
es and
vaginal atrophy
Atrophic vaginitis is inflammation of the vagina as a result of tissue thinning due to not enough estrogen. Symptoms may include pain with sex, vaginal itchiness or dryness, and an urge to urinate or burning with urination. It generally does no ...
in
postmenopausal or
ovariectomized women.
Estrone has also been used as an
antigonadotropin and form of
high-dose estrogen
High-dose estrogen (HDE) is a type of hormone therapy in which high doses of estrogens are given. When given in combination with a high dose of a progestogen, it has been referred to as pseudopregnancy. It is called this because the estrogen and p ...
to treat
prostate cancer
Prostate cancer is cancer of the prostate. Prostate cancer is the second most common cancerous tumor worldwide and is the fifth leading cause of cancer-related mortality among men. The prostate is a gland in the male reproductive system that sur ...
in men as well as a form of high-dose estrogen to treat
breast cancer
Breast cancer is cancer that develops from breast tissue. Signs of breast cancer may include a lump in the breast, a change in breast shape, dimpling of the skin, milk rejection, fluid coming from the nipple, a newly inverted nipple, or a re ...
in women.
It has since largely been discontinued and is mostly no longer available, having been superseded by other estrogens with better
potency
Potency may refer to:
* Potency (pharmacology), a measure of the activity of a drug in a biological system
* Virility
* Cell potency, a measure of the differentiation potential of stem cells
* In homeopathic dilutions, potency is a measure of how ...
and
pharmacokinetics
Pharmacokinetics (from Ancient Greek ''pharmakon'' "drug" and ''kinetikos'' "moving, putting in motion"; see chemical kinetics), sometimes abbreviated as PK, is a branch of pharmacology dedicated to determining the fate of substances administered ...
(namely
oral
The word oral may refer to:
Relating to the mouth
* Relating to the mouth, the first portion of the alimentary canal that primarily receives food and liquid
**Oral administration of medicines
** Oral examination (also known as an oral exam or oral ...
bioavailability and
duration
Duration may refer to:
* The amount of time elapsed between two events
* Duration (music) – an amount of time or a particular time interval, often cited as one of the fundamental aspects of music
* Duration (philosophy) – a theory of time and ...
).
Regardless of
route of administration
A route of administration in pharmacology and toxicology is the way by which a medication, drug, fluid, poison, or other substance is taken into the body.
Routes of administration are generally classified by the location at which the substance i ...
, if estrone is taken by a woman with an intact
uterus
The uterus (from Latin ''uterus'', plural ''uteri'') or womb () is the organ in the reproductive system of most female mammals, including humans that accommodates the embryonic and fetal development of one or more embryos until birth. The uter ...
, it should be combined with a
progestogen
Progestogens, also sometimes written progestagens or gestagens, are a class of natural or synthetic steroid hormones that bind to and activate the progesterone receptors (PR). Progesterone is the major and most important progestogen in the body. ...
such as
progesterone
Progesterone (P4) is an endogenous steroid and progestogen sex hormone involved in the menstrual cycle, pregnancy, and embryogenesis of humans and other species. It belongs to a group of steroid hormones called the progestogens and is the m ...
to offset the risk of
endometrial hyperplasia and
cancer
Cancer is a group of diseases involving abnormal cell growth with the potential to invade or spread to other parts of the body. These contrast with benign tumors, which do not spread. Possible signs and symptoms include a lump, abnormal b ...
.
Estrone has been used by intramuscular injection at a dosage of 0.1 to 2 mg per week, or 0.1 to 0.5 mg given 2 or 3 times per week, for the treatment of
menopausal symptoms such as hot flashes and vaginal atrophy,
and at a dosage of 0.1 to 1.0 mg weekly in single or divided doses for the treatment of female
hypogonadism,
surgical castration, and
primary ovarian failure
Primary ovarian insufficiency (POI) (also called premature ovarian insufficiency, premature menopause, and premature ovarian failure) is the partial or total loss of reproductive and hormonal function of the ovaries before age 40 because of foll ...
.
The range of single doses of estrone by intramuscular injection that are typically used clinically in women is 0.1 to 5 mg.
High doses of intramuscular estrone have been used for prostate cancer in men and for breast cancer in women.
Available forms
Estrone for
intramuscular injection
Intramuscular injection, often abbreviated IM, is the injection of a substance into a muscle. In medicine, it is one of several methods for parenteral administration of medications. Intramuscular injection may be preferred because muscles have ...
was provided as 1, 2, 2.5, 3, 4, and 5 mg/mL
aqueous suspension
In chemistry, a suspension is a Mixture#Homogeneous and heterogeneous mixtures, heterogeneous mixture of a fluid that contains solid particles sufficiently large for sedimentation. The particles may be macroscopic, visible to the naked eye, usual ...
s and/or
oil solution
An oil is any nonpolar chemical substance that is composed primarily of hydrocarbons and is hydrophobic (does not mix with water) & lipophilic (mixes with other oils). Oils are usually flammable and surface active. Most oils are unsaturated ...
s.
[https://www.micromedexsolutions.com/micromedex2/ ] It has also been available in the form of
vaginal
In mammals, the vagina is the elastic, muscular part of the female genital tract. In humans, it extends from the vestibule to the cervix. The outer vaginal opening is normally partly covered by a thin layer of mucosal tissue called the hyme ...
cream
Cream is a dairy product composed of the higher-fat layer skimmed from the top of milk before homogenization. In un-homogenized milk, the fat, which is less dense, eventually rises to the top. In the industrial production of cream, this process ...
s (1 mg/g (0.1%)) and
suppositories
A suppository is a dosage form used to deliver medications by insertion into a body orifice where it dissolves or melts to exert local or systemic effects. There are three types of suppositories, each to insert into a different sections: rectal su ...
(0.2 mg, 0.25 mg) as well as
subcutaneous pellet implant
In medicine, a subcutaneous implant, or subcutaneous pellet, is an implant that is delivered under the skin into the subcutaneous tissue by surgery or injection and is used to deliver a drug for a long period of time. Examples of drugs that can ...
s and
oral
The word oral may refer to:
Relating to the mouth
* Relating to the mouth, the first portion of the alimentary canal that primarily receives food and liquid
**Oral administration of medicines
** Oral examination (also known as an oral exam or oral ...
tablet
Tablet may refer to:
Medicine
* Tablet (pharmacy), a mixture of pharmacological substances pressed into a small cake or bar, colloquially called a "pill"
Computing
* Tablet computer, a mobile computer that is primarily operated by touching the s ...
s (1.25 mg).
A combined
oral
The word oral may refer to:
Relating to the mouth
* Relating to the mouth, the first portion of the alimentary canal that primarily receives food and liquid
**Oral administration of medicines
** Oral examination (also known as an oral exam or oral ...
tablet
Tablet may refer to:
Medicine
* Tablet (pharmacy), a mixture of pharmacological substances pressed into a small cake or bar, colloquially called a "pill"
Computing
* Tablet computer, a mobile computer that is primarily operated by touching the s ...
formulation containing
estradiol (0.3 mg, 0.6 mg), estrone (0.7 mg, 1.4 mg), and
estriol (0.135 mg, 0.27 mg) has been marketed under the brand name Hormonin as well.
In addition, a combined injectable preparation containing estrone (1 mg) and
progesterone
Progesterone (P4) is an endogenous steroid and progestogen sex hormone involved in the menstrual cycle, pregnancy, and embryogenesis of humans and other species. It belongs to a group of steroid hormones called the progestogens and is the m ...
(10 mg) is available in the form of
ampoules under the brand name Synergon.
[https://serp.mc/wp-content/uploads/2018/05/synergon.pdf ]
Although estrone by intramuscular injection was originally formulated as an oil solution, it was soon replaced by formulations of estrone as an aqueous suspension due to a longer duration of action of these formulations.
Side effects
Side effects of estrogens like estrone include
breast tenderness,
breast enlargement,
headache
Headache is the symptom of pain in the face, head, or neck. It can occur as a migraine, tension-type headache, or cluster headache. There is an increased risk of depression in those with severe headaches.
Headaches can occur as a result ...
,
nausea
Nausea is a diffuse sensation of unease and discomfort, sometimes perceived as an urge to vomit. While not painful, it can be a debilitating symptom if prolonged and has been described as placing discomfort on the chest, abdomen, or back of the ...
,
fluid retention, and
edema
Edema, also spelled oedema, and also known as fluid retention, dropsy, hydropsy and swelling, is the build-up of fluid in the body's Tissue (biology), tissue. Most commonly, the legs or arms are affected. Symptoms may include skin which feels t ...
, among others.
It can also cause
endometrial hyperplasia.
Pharmacology
Pharmacodynamics
Mechanism of action
Estrone is an estrogen, specifically an
agonist
An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...
of the
estrogen receptors (ERs)
ERα
Estrogen receptor alpha (ERα), also known as NR3A1 (nuclear receptor subfamily 3, group A, member 1), is one of two main types of estrogen receptor, a nuclear receptor (mainly found as a chromatin-binding protein)
that is activated by the sex ...
and
ERβ
Estrogen receptor beta (ERβ) also known as NR3A2 (nuclear receptor subfamily 3, group A, member 2) is one of two main types of estrogen receptor—a nuclear receptor which is activated by the sex hormone estrogen. In humans ERβ is encoded by ...
.
It is a far less
potent estrogen than is estradiol, and as such is a relatively weak estrogen.
Given by
subcutaneous injection
Subcutaneous administration is the insertion of medications beneath the skin either by injection or infusion.
A subcutaneous injection is administered as a bolus into the subcutis, the layer of skin directly below the dermis and epidermis, ...
in mice, estradiol is about 10-fold more potent than estrone and about 100-fold more potent than
estriol.
According to one study, the
relative binding affinities
In biochemistry and pharmacology, a ligand is a substance that forms a complex with a biomolecule to serve a biological purpose. The etymology stems from ''ligare'', which means 'to bind'. In protein-ligand binding, the ligand is usually a mole ...
of estrone for the human ERα and ERβ were 4.0% and 3.5% of those estradiol, respectively, and the
relative transactivational capacities
Intrinsic activity (IA) and efficacy refer to the relative ability of a drug-receptor complex to produce a maximum functional response. This must be distinguished from the affinity, which is a measure of the ability of the drug to bind to its mole ...
of estrone at the ERα and ERβ were 2.6% and 4.3% of those of estradiol, respectively.
In accordance, the estrogenic activity of estrone has been reported to be approximately 4% of that of estradiol.
Other studies have reported that estrone has about one-tenth of the potency of estradiol in activating the ERs ''in vitro''.
Because estrone can be
transformed into estradiol, which is far more potent as an estrogen in comparison, most or all of the estrogenic potency of estrone ''
in vivo
Studies that are ''in vivo'' (Latin for "within the living"; often not italicized in English) are those in which the effects of various biological entities are tested on whole, living organisms or cells, usually animals, including humans, and ...
'' is actually due to conversion into estradiol.
As such, similarly to the case of
estrone sulfate
Estrone sulfate, also known as E1S, E1SO4 and estrone 3-sulfate, is a natural, endogenous steroid and an estrogen ester and conjugate.
In addition to its role as a natural hormone, estrone sulfate is used as a medication, for instance in menop ...
, estrone is considered to be a
prodrug
A prodrug is a medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug ...
of estradiol.
Some ''
in vitro
''In vitro'' (meaning in glass, or ''in the glass'') studies are performed with microorganisms, cells, or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in biology an ...
'' research has suggested that estrone might be able to
partially antagonize the actions of estradiol,
but this does not appear to be of clinical significance.
In contrast to estradiol and estriol, estrone is not a
ligand
In coordination chemistry, a ligand is an ion or molecule (functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's electr ...
of the
G protein-coupled estrogen receptor
G protein-coupled estrogen receptor 1 (GPER), also known as G protein-coupled receptor 30 (GPR30), is a protein that in humans is encoded by the ''GPER'' gene. GPER binds to and is activated by the female sex hormone estradiol and is responsible ...
(affinity >10,000 nM).
Effects in the body and brain
In
clinical research
Clinical research is a branch of healthcare science that determines the safety and effectiveness ( efficacy) of medications, devices, diagnostic products and treatment regimens intended for human use. These may be used for prevention, treatm ...
in the 1930s, estrone was given via intramuscular injection to
ovariectomized women in order to study its effects and to elucidate the
biological properties of estrogens in humans.
In these studies, prior to administration of estrone,
amenorrhea,
atrophy
Atrophy is the partial or complete wasting away of a part of the body. Causes of atrophy include mutations (which can destroy the gene to build up the organ), poor nourishment, poor circulation, loss of hormonal support, loss of nerve supply t ...
of the
breast
The breast is one of two prominences located on the upper ventral region of a primate's torso. Both females and males develop breasts from the same embryological tissues.
In females, it serves as the mammary gland, which produces and secret ...
s (as well as
flaccidity
Flaccid paralysis is a neurological condition characterized by weakness or paralysis and reduced muscle tone without other obvious cause (e.g., trauma). This abnormal condition may be caused by disease or by trauma affecting the nerves associat ...
and small and non-erectile
nipple
The nipple is a raised region of tissue on the surface of the breast from which, in females, milk leaves the breast through the lactiferous ducts to feed an infant. The milk can flow through the nipple passively or it can be ejected by smooth mu ...
s),
vagina
In mammals, the vagina is the elastic, muscular part of the female genital tract. In humans, it extends from the vestibule to the cervix. The outer vaginal opening is normally partly covered by a thin layer of mucosal tissue called the hymen ...
, and
endometrium
The endometrium is the inner epithelial layer, along with its mucous membrane, of the mammalian uterus. It has a basal layer and a functional layer: the basal layer contains stem cells which regenerate the functional layer. The functional laye ...
,
vaginal dryness
Vaginal lubrication is a naturally produced fluid that lubricates a
vagina. Vaginal lubrication is always present, but production increases significantly near ovulation and during sexual arousal in anticipation of sexual intercourse. Vaginal ...
, and
subjective symptoms of ovariectomy (e.g.,
hot flashes,
mood changes) were all present in the women.
Treatment with estrone was found to dose- and time-dependently produce a variety of effects, including breast changes,
reproductive tract
The reproductive system of an organism, also known as the genital system, is the biological system made up of all the anatomical sex organs, organs involved in sexual reproduction. Many non-living substances such as fluids, hormones, and pherom ...
changes of the vagina,
cervix
The cervix or cervix uteri (Latin, 'neck of the uterus') is the lower part of the uterus (womb) in the human female reproductive system. The cervix is usually 2 to 3 cm long (~1 inch) and roughly cylindrical in shape, which changes during ...
, and
endometrium
The endometrium is the inner epithelial layer, along with its mucous membrane, of the mammalian uterus. It has a basal layer and a functional layer: the basal layer contains stem cells which regenerate the functional layer. The functional laye ...
/
uterus
The uterus (from Latin ''uterus'', plural ''uteri'') or womb () is the organ in the reproductive system of most female mammals, including humans that accommodates the embryonic and fetal development of one or more embryos until birth. The uter ...
, and relief from the subjective symptoms of ovariectomy, as well as increased
libido.
Breast changes specifically included
enlargement and a sense of
fullness, increased
sensitivity and
pigmentation of the nipples as well as
nipple erection
The nipple is a raised region of tissue on the surface of the breast from which, in females, milk leaves the breast through the lactiferous ducts to feed an infant. The milk can flow through the nipple passively or it can be ejected by smooth mu ...
,
tingling
Paresthesia is an abnormal sensation of the skin (tingling, pricking, chilling, burning, numbness) with no apparent physical cause. Paresthesia may be transient or chronic, and may have any of dozens of possible underlying causes. Paresthesias ar ...
within the breast
mammary gland
A mammary gland is an exocrine gland in humans and other mammals that produces milk to feed young offspring. Mammals get their name from the Latin word ''mamma'', "breast". The mammary glands are arranged in organs such as the breasts in primat ...
ular tissue, and
aching and soreness of the breasts.
Reproductive tract
The reproductive system of an organism, also known as the genital system, is the biological system made up of all the anatomical sex organs, organs involved in sexual reproduction. Many non-living substances such as fluids, hormones, and pherom ...
changes included increased
growth
Growth may refer to:
Biology
* Auxology, the study of all aspects of human physical growth
* Bacterial growth
* Cell growth
* Growth hormone, a peptide hormone that stimulates growth
* Human development (biology)
* Plant growth
* Secondary growth ...
, thickness, and
differentiation of the endometrium, and reversal of vaginal and cervical atrophy, which were accompanied by increased
congestion of the cervix and
mucous discharge from the cervix, uterine
cramps and
needle-like pains, pelvic fullness, a "bearing-down" sensation, and increased
vaginal lubrication
Vaginal lubrication is a naturally produced fluid that lubricates a
vagina. Vaginal lubrication is always present, but production increases significantly near ovulation and during sexual arousal in anticipation of sexual intercourse. Vaginal dr ...
, as well as
uterine bleeding
Vaginal bleeding is any expulsion of blood from the vagina. This bleeding may originate from the uterus, vaginal wall, or cervix. Generally, it is either part of a normal menstrual cycle or is caused by hormonal or other problems of the reproductiv ...
both during treatment and in the days following cessation of injections.
Endometrial hyperplasia also occurred with sufficiently high doses of estrone.
Clinical research has confirmed the nature of estrone as an
inactive prodrug
A prodrug is a medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug ...
of estradiol.
With
oral administration
Oral administration is a route of administration where a substance is taken through the mouth. Per os abbreviated to P.O. is sometimes used as a direction for medication to be taken orally. Many medications are taken orally because they are in ...
of estradiol, the ratio of estradiol levels to estrone levels is about 5 times higher on average than under normal
physiological
Physiology (; ) is the scientific study of functions and mechanisms in a living system. As a sub-discipline of biology, physiology focuses on how organisms, organ systems, individual organs, cells, and biomolecules carry out the chemical ...
circumstances in
premenopausal women and with
parenteral
A route of administration in pharmacology and toxicology is the way by which a drug, fluid, poison, or other substance is taken into the body.
Routes of administration are generally classified by the location at which the substance is applied. ...
(non-oral)
route
Route or routes may refer to:
* Route (gridiron football), a path run by a wide receiver
* route (command), a program used to configure the routing table
* Route, County Antrim, an area in Northern Ireland
* ''The Route'', a 2013 Ugandan film
* Ro ...
s of estradiol.
Oral administration of
menopausal replacement dosages of estradiol results in low,
follicular phase
The follicular phase, also known as the preovulatory phase or proliferative phase, is the phase of the estrous cycle (or, in primates for example, the menstrual cycle) during which follicles in the ovary mature from primary follicle to a ful ...
levels of estradiol, whereas estrone levels resemble the high levels seen during the
first trimester of
pregnancy
Pregnancy is the time during which one or more offspring develops ( gestates) inside a woman's uterus (womb). A multiple pregnancy involves more than one offspring, such as with twins.
Pregnancy usually occurs by sexual intercourse, but ca ...
.
In spite of markedly elevated levels of estrone with oral estradiol but not with
transdermal estradiol, clinical studies have shown that doses of oral and transdermal estradiol achieving similar levels of estradiol possess equivalent and non-significantly different
potency
Potency may refer to:
* Potency (pharmacology), a measure of the activity of a drug in a biological system
* Virility
* Cell potency, a measure of the differentiation potential of stem cells
* In homeopathic dilutions, potency is a measure of how ...
in terms of measures including suppression of
luteinizing hormone and
follicle-stimulating hormone
Follicle-stimulating hormone (FSH) is a gonadotropin, a glycoprotein polypeptide hormone. FSH is synthesized and secreted by the gonadotropic cells of the anterior pituitary gland and regulates the development, growth, pubertal maturation, an ...
levels, inhibition of
bone resorption, and relief of
menopausal symptoms such as
hot flash
Hot flashes (also known as hot flushes) are a form of flushing, often caused by the changing hormone levels that are characteristic of menopause. They are typically experienced as a feeling of intense heat with sweating and rapid heartbeat, and ...
es.
In addition, estradiol levels were found to correlate with these effects, while estrone levels did not.
These findings confirm that estrone has very low estrogenic activity, and also indicate that estrone does not diminish the estrogenic activity of estradiol.
This contradicts some
cell-free ''
in-vitro'' research suggesting that high concentrations of estrone might be able to
partially antagonize the actions of estradiol.
Pharmacokinetics
Absorption
Like estradiol, estrone has poor
oral
The word oral may refer to:
Relating to the mouth
* Relating to the mouth, the first portion of the alimentary canal that primarily receives food and liquid
**Oral administration of medicines
** Oral examination (also known as an oral exam or oral ...
bioavailability.
It has been said that, taken by mouth in non-
micronized
Micronization is the process of reducing the average diameter of a solid material's particles. Traditional techniques for micronization focus on mechanical means, such as milling and grinding. Modern techniques make use of the properties of superc ...
form, a dose of 25 mg estrone is approximately equivalent to 2.5 mg
conjugated estrogens, 50 µg
ethinylestradiol, or 1 mg
diethylstilbestrol
Diethylstilbestrol (DES), also known as stilbestrol or stilboestrol, is a nonsteroidal estrogen medication, which is presently rarely used. In the past, it was widely used for a variety of indications, including pregnancy support for those with a ...
in terms of estrogenic potency.
Due to its weak oral activity, estrone has been used
parenteral
A route of administration in pharmacology and toxicology is the way by which a drug, fluid, poison, or other substance is taken into the body.
Routes of administration are generally classified by the location at which the substance is applied. ...
ly instead, for instance by
intramuscular injection
Intramuscular injection, often abbreviated IM, is the injection of a substance into a muscle. In medicine, it is one of several methods for parenteral administration of medications. Intramuscular injection may be preferred because muscles have ...
or
vaginal administration
Intravaginal administration is a route of administration where the substance is applied inside the vagina. Pharmacologically, it has the potential advantage to result in effects primarily in the vagina or nearby structures (such as the vaginal po ...
.
The
pharmacokinetics
Pharmacokinetics (from Ancient Greek ''pharmakon'' "drug" and ''kinetikos'' "moving, putting in motion"; see chemical kinetics), sometimes abbreviated as PK, is a branch of pharmacology dedicated to determining the fate of substances administered ...
of vaginal estrone have been studied.
Estrone in oil solution by intramuscular injection has a shorter duration than estrone in aqueous suspension by intramuscular injection.
Estrone in oil solution by intramuscular injection is rapidly absorbed, while estrone in aqueous suspension has a prolonged period of absorption.
Upon intramuscular injection of estrone in aqueous solution, the water from the preparation is absorbed and a microcrystalline depot of estrone that is slowly absorbed by the body is formed.
This is responsible for the prolonged duration of estrone in aqueous suspension compared to oil solution.
Distribution
Unlike estradiol and estriol, estrone is not accumulated in target
tissues.
In terms of
plasma protein binding
Plasma protein binding refers to the degree to which medications attach to proteins within the blood. A drug's efficiency may be affected by the degree to which it binds. The less bound a drug is, the more efficiently it can traverse or diffuse th ...
, estrone is bound approximately 16% to
sex hormone-binding globulin (SHBG) and 80% to
albumin
Albumin is a family of globular proteins, the most common of which are the serum albumins. All the proteins of the albumin family are water-soluble, moderately soluble in concentrated salt solutions, and experience heat denaturation. Albumins ...
,
with the remainder (2.0 to 4.0%) circulating free or unbound.
Estrone has about 24% of the relative binding affinity of estradiol for SHBG, and hence is relatively poorly bound to SHBG.
Metabolism
Estrone is
conjugated into
estrogen conjugate
An estrogen conjugate is a conjugate of an endogenous estrogen. They occur naturally in the body as metabolites of estrogens and can be reconverted back into estrogens. They serve as a circulating reservoir for estrogen, particularly in the c ...
s such as
estrone sulfate
Estrone sulfate, also known as E1S, E1SO4 and estrone 3-sulfate, is a natural, endogenous steroid and an estrogen ester and conjugate.
In addition to its role as a natural hormone, estrone sulfate is used as a medication, for instance in menop ...
and
estrone glucuronide
Estrone glucuronide, or estrone-3-D-glucuronide, is a conjugated metabolite of estrone. It is formed from estrone in the liver by UDP-glucuronyltransferase via attachment of glucuronic acid and is eventually excreted in the urine by the kidneys. ...
by
sulfotransferases and
glucuronidases, and can also be
hydroxylated
In chemistry, hydroxylation can refer to:
*(i) most commonly, hydroxylation describes a chemistry, chemical process that introduces a hydroxyl group () into an organic compound.
*(ii) the ''degree of hydroxylation'' refers to the number of OH gr ...
by
cytochrome P450
Cytochromes P450 (CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that functions as monooxygenases. In mammals, these proteins oxidize steroids, fatty acids, and xenobiotics, and are ...
enzymes into
catechol estrogen
A catechol estrogen is a steroidal estrogen that contains catechol (1,2-dihydroxybenzene) within its structure. The catechol estrogens are endogenous metabolites of estradiol and estrone and include the following compounds:
* 2-Hydroxylated:
** ...
s such as
2-hydroxyestrone and
4-hydroxyestrone or into
estriol.
Both of these transformations take place predominantly in the
liver
The liver is a major Organ (anatomy), organ only found in vertebrates which performs many essential biological functions such as detoxification of the organism, and the Protein biosynthesis, synthesis of proteins and biochemicals necessary for ...
.
Estrone can also be reversibly converted into estradiol by
17β-hydroxysteroid dehydrogenase
A hydroxysteroid is a molecule derived from a steroid with a hydrogen replaced with a hydroxy group. When the hydroxy group is specifically at the C3 position, hydroxysteroids are referred to as sterols, with an example being cholesterol.
See ...
s (17β-HSDs), and this accounts for most or all of its estrogenic activity.
17β-HSD
isoform
A protein isoform, or "protein variant", is a member of a set of highly similar proteins that originate from a single gene or gene family and are the result of genetic differences. While many perform the same or similar biological roles, some isof ...
s that are involved in the conversion of estrone into estradiol include
17β-HSD1,
17β-HSD3,
17β-HSD4,
17β-HSD7,
17β-HSD8, and
17β-HSD12, although the relative contributions of the different isoforms is unknown.
The
biological half-lives of estrone and estradiol in the circulation are both about 10 to 70 minutes, whereas the biological half-life of estrone sulfate in the circulation is about 10 to 12 hours.
The
metabolic clearance rate of estrone is 1,050 L/day/m
2 and of estradiol is 580 L/day/m
2, while that of estrone sulfate is 80 L/day/m
2.
For comparison, the metabolic clearance rate of estriol is 1,110 L/day/m
2.
A single 1 to 2 mg dose of estrone in oil solution by intramuscular injection has a duration of about 2 or 3 days.
As an
aqueous suspension
In chemistry, a suspension is a Mixture#Homogeneous and heterogeneous mixtures, heterogeneous mixture of a fluid that contains solid particles sufficiently large for sedimentation. The particles may be macroscopic, visible to the naked eye, usual ...
by
intramuscular injection
Intramuscular injection, often abbreviated IM, is the injection of a substance into a muscle. In medicine, it is one of several methods for parenteral administration of medications. Intramuscular injection may be preferred because muscles have ...
, estrone was used at a dose of 0.1 to 0.5 mg 2 to 3 times per week, or at a dose of 0.1 to 2 mg once a week or in divided doses.
In one rodent study,
exogenous
In a variety of contexts, exogeny or exogeneity () is the fact of an action or object originating externally. It contrasts with endogeneity or endogeny, the fact of being influenced within a system.
Economics
In an economic model, an exogeno ...
estrone was administered and increased circulating estradiol levels by about 10-fold; co-administration of a
selective 17β-HSD1
inhibitor
Inhibitor or inhibition may refer to:
In biology
* Enzyme inhibitor, a substance that binds to an enzyme and decreases the enzyme's activity
* Reuptake inhibitor, a substance that increases neurotransmission by blocking the reuptake of a neurotra ...
decreased estradiol levels by about 50%.
The ratio of circulating estrone to circulating estradiol is the same at about 5:1 with both oral estradiol and oral estrone sulfate.
An investigational estrone
vaginal ring
Vaginal rings (also known as intravaginal rings, or V-Rings) are polymeric drug delivery devices designed to provide controlled release of drugs for intravaginal administration over extended periods of time. The ring is inserted into the vagina a ...
was found to result in a ratio of estrone to estradiol of 4:1 or 5:1 initially, but this decreased to about 1:1 with continuous therapy.
Excretion
Estrone is
excreted
Excretion is a process in which metabolic waste
is eliminated from an organism. In vertebrates this is primarily carried out by the lungs, kidneys, and skin. This is in contrast with secretion, where the substance may have specific tasks after lea ...
in
urine
Urine is a liquid by-product of metabolism in humans and in many other animals. Urine flows from the kidneys through the ureters to the urinary bladder. Urination results in urine being excretion, excreted from the body through the urethra.
Cel ...
in the form of
estrogen conjugate
An estrogen conjugate is a conjugate of an endogenous estrogen. They occur naturally in the body as metabolites of estrogens and can be reconverted back into estrogens. They serve as a circulating reservoir for estrogen, particularly in the c ...
s such as
estrone sulfate
Estrone sulfate, also known as E1S, E1SO4 and estrone 3-sulfate, is a natural, endogenous steroid and an estrogen ester and conjugate.
In addition to its role as a natural hormone, estrone sulfate is used as a medication, for instance in menop ...
and
estrone glucuronide
Estrone glucuronide, or estrone-3-D-glucuronide, is a conjugated metabolite of estrone. It is formed from estrone in the liver by UDP-glucuronyltransferase via attachment of glucuronic acid and is eventually excreted in the urine by the kidneys. ...
.
Following an intravenous injection of
labeled estrone in women, almost 90% is excreted in urine and
feces
Feces ( or faeces), known colloquially and in slang as poo and poop, are the solid or semi-solid remains of food that was not digested in the small intestine, and has been broken down by bacteria in the large intestine. Feces contain a relati ...
within 4 to 5 days.
Enterohepatic recirculation
Enterohepatic circulation refers to the circulation of biliary acids, bilirubin, drugs or other substances from the liver to the bile, followed by entry into the small intestine, absorption by the enterocyte and transport back to the liver. E ...
causes a delay in excretion of estrone.
Chemistry
Estrone, also known as estra-1,3,5(10)-trien-3-ol-17-one, is a
naturally occurring
A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synt ...
estrane
Estrane is a C18 steroid derivative, with a gonane core.
''Estrenes'' are estrane derivatives that contain a double bond, with an example being nandrolone. ''Estratrienes'' (estrins) are estrane derivatives that contain three double bonds, for i ...
steroid
A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and a ...
with
double bonds at the C1, C3, and C5 positions, a
hydroxyl group
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy g ...
at the C3 position, and a
ketone
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...
group at the C17 position.
The name ''estrone'' was derived from the chemical terms ''
estrin'' (estra-1,3,5(10)-triene) and ''ketone''.
A variety of
estrone esters have been
synthesized and described.
These include the marketed esters
estrone acetate
Estrone acetate (brand name Hovigal) is a semisynthetic, steroidal estrogen. It is an estrogen ester, specifically, an ester of estrone.
See also
* Hydroxyestrone diacetate
* Estradiol acetate
Estradiol acetate (EA), sold under the brand n ...
,
estrone sulfate
Estrone sulfate, also known as E1S, E1SO4 and estrone 3-sulfate, is a natural, endogenous steroid and an estrogen ester and conjugate.
In addition to its role as a natural hormone, estrone sulfate is used as a medication, for instance in menop ...
,
estrone tetraacetylglucoside
Estrone tetraacetylglucoside (brand name Glucovex, Glycovex) is a semisynthetic, steroidal estrogen. It is an estrogen ester, specifically, an ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in whic ...
, and
estropipate
Estropipate, also known as piperazine estrone sulfate and sold under the brand names Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others, is an estrogen medication which is used mainly in menopausal hormone therapy in the treatment ...
(piperazine estrone sulfate), and the never-marketed esters
estrone benzoate,
estrone cyanate
Estrone cyanate, or estrone 3-''O''-cyanate, also known as estrocyanate, is an estrogen and an estrogen ester – specifically, the 3-O-cyanate ester of estrone – which was investigated for potential use in birth control pills but was found to ...
,
estrone glucuronide
Estrone glucuronide, or estrone-3-D-glucuronide, is a conjugated metabolite of estrone. It is formed from estrone in the liver by UDP-glucuronyltransferase via attachment of glucuronic acid and is eventually excreted in the urine by the kidneys. ...
, and
estrone sulfamate.
History
In 1927,
Bernhard Zondek
Bernhard Zondek ( he, ברנרד צונדק; 29 July 1891 – 8 November 1966) was a German-born Israeli gynecologist who developed the first reliable pregnancy test in 1928.
Biography
Bernhard Zondek was born in Wronke, Germany, now Wronki, Po ...
and
Selmar Aschheim
Selmar Aschheim (4 October 1878 – 15 February 1965) was a German gynecologist who was a native resident of Berlin.
Born into a Jewish family, in 1902 he received a doctorate of medicine in Freiburg, and later became director of the laboratory ...
discovered that large amounts of estrogens were
excreted
Excretion is a process in which metabolic waste
is eliminated from an organism. In vertebrates this is primarily carried out by the lungs, kidneys, and skin. This is in contrast with secretion, where the substance may have specific tasks after lea ...
in the
urine
Urine is a liquid by-product of metabolism in humans and in many other animals. Urine flows from the kidneys through the ureters to the urinary bladder. Urination results in urine being excretion, excreted from the body through the urethra.
Cel ...
of
pregnant
Pregnancy is the time during which one or more offspring develops (gestation, gestates) inside a woman, woman's uterus (womb). A multiple birth, multiple pregnancy involves more than one offspring, such as with twins.
Pregnancy usually occur ...
women.
This rich source of estrogens allowed the development of potent estrogenic formulations for
scientific and
clinical use.
In 1929, pure crystalline estrone was isolated from the urine of pregnant women by various researchers.
By 1929,
pharmaceutical preparations including ''Amniotin'' (
Squibb
Squib or Squibb may refer to:
* Squib (explosive), a miniature explosive with a very small charge
** Bullet hit squib, a practical effect simulating a gunshot wound in film and theatre
* Squib (''Harry Potter'')
* Squib (''Star Wars'')
* Squib ( ...
), ''Progynon'' (
Schering), and ''Theelin'' (
Parke-Davis
Parke-Davis is a subsidiary of the pharmaceutical company Pfizer. Although Parke, Davis & Co. is no longer an independent corporation, it was once America's oldest and largest drug maker, and played an important role in medical history. In 1970 ...
), purified from pregnancy urine,
placenta
The placenta is a temporary embryonic and later fetal organ that begins developing from the blastocyst shortly after implantation. It plays critical roles in facilitating nutrient, gas and waste exchange between the physically separate mater ...
s, and/or
amniotic fluid
The amniotic fluid is the protective liquid contained by the amniotic sac of a gravid amniote. This fluid serves as a cushion for the growing fetus, but also serves to facilitate the exchange of nutrients, water, and biochemical products betwee ...
and containing purified estrone or
mixtures of estrogens that included estrone, were being sold commercially for use by
intramuscular injection
Intramuscular injection, often abbreviated IM, is the injection of a substance into a muscle. In medicine, it is one of several methods for parenteral administration of medications. Intramuscular injection may be preferred because muscles have ...
.
Other products and brand names of estrone marketed in the 1930s included ''Estrone'' (
Abbott,
Lilly), ''Oestroform'' (
British Drug Houses
The Merck Group, branded and commonly known as Merck, is a German multinational science and technology company headquartered in Darmstadt, with about 60,000 employees and present in 66 countries. The group includes around 250 companies; the m ...
), ''Folliculin'' (
Organon), ''Menformon'' (
Organon), and ''Ketodestrin'' (Paines & Byrne), among others.
These formulations included
ampoules of
oil or
aqueous solution
An aqueous solution is a solution in which the solvent is water. It is mostly shown in chemical equations by appending (aq) to the relevant chemical formula. For example, a solution of table salt, or sodium chloride (NaCl), in water would be re ...
for
intramuscular injection
Intramuscular injection, often abbreviated IM, is the injection of a substance into a muscle. In medicine, it is one of several methods for parenteral administration of medications. Intramuscular injection may be preferred because muscles have ...
,
oral
The word oral may refer to:
Relating to the mouth
* Relating to the mouth, the first portion of the alimentary canal that primarily receives food and liquid
**Oral administration of medicines
** Oral examination (also known as an oral exam or oral ...
tablet
Tablet may refer to:
Medicine
* Tablet (pharmacy), a mixture of pharmacological substances pressed into a small cake or bar, colloquially called a "pill"
Computing
* Tablet computer, a mobile computer that is primarily operated by touching the s ...
s, and
vaginal
In mammals, the vagina is the elastic, muscular part of the female genital tract. In humans, it extends from the vestibule to the cervix. The outer vaginal opening is normally partly covered by a thin layer of mucosal tissue called the hyme ...
suppositories
A suppository is a dosage form used to deliver medications by insertion into a body orifice where it dissolves or melts to exert local or systemic effects. There are three types of suppositories, each to insert into a different sections: rectal su ...
.
Estrone in
aqueous suspension
In chemistry, a suspension is a Mixture#Homogeneous and heterogeneous mixtures, heterogeneous mixture of a fluid that contains solid particles sufficiently large for sedimentation. The particles may be macroscopic, visible to the naked eye, usual ...
for use by intramuscular injection was first described in 1941 and was introduced for medical use under the brand name ''Theelin Aqueous Suspension'' by 1944.
Society and culture
Generic names
''Estrone'' is the
generic name of estrone in
American English
American English, sometimes called United States English or U.S. English, is the set of variety (linguistics), varieties of the English language native to the United States. English is the Languages of the United States, most widely spoken lan ...
and its , , , , , and .
''Oestrone'', in which the "O" is silent, was the former of estrone and its name in
British English
British English (BrE, en-GB, or BE) is, according to Lexico, Oxford Dictionaries, "English language, English as used in Great Britain, as distinct from that used elsewhere". More narrowly, it can refer specifically to the English language in ...
,
but the spelling was eventually changed to ''estrone''.
Brand names
Estrone has been marketed under a variety of brand names, including Andrestraq, Aquacrine, A.T.V., Bestrone, Centrogen, Cicatral, Cormone, Crinovaryl, Cristallovar, Crystogen, Destrone, Disynformon, Endofolliculina, Estragyn, Estroject, Estrol, Estrone, Estrone Aqueous Suspension, Estrone-A, Estrugenone, Estrusol, Femestrone, Femidyn, Folikrin, Folipex, Folisan, Folliculin, Follicunodis, Follidrin, Gineburno, Glandubolin, Grietalgen, Grietalgen Hidrocort, Gynogen, Hiestrone, Hormofollin, Hormonin, Hormovarine, Kestrin, Kestrone, Ketodestrin, Kolpon, Ladies Pearl, Livifolin, Menagen, Metharmon-F, Neo-Estrone, Oestrilin, Oestrin, Oestroform, Oestroperos, Ovex, Ovifollin, Perlatan, Progynon, Senikolp, Solliculin, Solutio Folliculinum, Synergon (in combination with
progesterone
Progesterone (P4) is an endogenous steroid and progestogen sex hormone involved in the menstrual cycle, pregnancy, and embryogenesis of humans and other species. It belongs to a group of steroid hormones called the progestogens and is the m ...
), Theelin, Thynestron, Tokokin, Unden, Unigen, Wehgen, and Wynestron.
Brand names of estrone in aqueous suspension specifically include Bestrone, Estaqua, Estrofol, Estroject, Estrone-A, Estronol, Femogen, Foygen Aqueous, Gravigen Aqueous, Gynogen, Hormogen-A, Kestrin Aqueous, Kestrone, Theelin Aqueous, Theogen, Unigen, and Wehgen.
Availability
Although estrone has been widely marketed in the past, it has mostly been discontinued and remains available in only a few countries.
These countries reportedly include
Canada
Canada is a country in North America. Its ten provinces and three territories extend from the Atlantic Ocean to the Pacific Ocean and northward into the Arctic Ocean, covering over , making it the world's second-largest country by tot ...
,
Georgia,
Monaco
Monaco (; ), officially the Principality of Monaco (french: Principauté de Monaco; Ligurian: ; oc, Principat de Mónegue), is a sovereign city-state and microstate on the French Riviera a few kilometres west of the Italian region of Lig ...
, and
Taiwan
Taiwan, officially the Republic of China (ROC), is a country in East Asia, at the junction of the East and South China Seas in the northwestern Pacific Ocean, with the People's Republic of China (PRC) to the northwest, Japan to the nort ...
.
However, estrone remains widely available throughout the world in the form of
estrone sulfate
Estrone sulfate, also known as E1S, E1SO4 and estrone 3-sulfate, is a natural, endogenous steroid and an estrogen ester and conjugate.
In addition to its role as a natural hormone, estrone sulfate is used as a medication, for instance in menop ...
, which can be found in
estropipate
Estropipate, also known as piperazine estrone sulfate and sold under the brand names Harmogen, Improvera, Ogen, Ortho-Est, and Sulestrex among others, is an estrogen medication which is used mainly in menopausal hormone therapy in the treatment ...
(piperazine estrone sulfate),
conjugated estrogens (Premarin), and
esterified estrogens (Estratab, Menest).
Research
An estrone
vaginal ring
Vaginal rings (also known as intravaginal rings, or V-Rings) are polymeric drug delivery devices designed to provide controlled release of drugs for intravaginal administration over extended periods of time. The ring is inserted into the vagina a ...
was developed and studied for use in menopausal hormone therapy.
It increased estrogen levels, suppressed
gonadotropin levels, and relieved menopausal symptoms.
Subcutaneous pellet implantation of estrone has also been studied.
See also
*
Estradiol/estrone/estriol
Estradiol/estrone/estriol (brand name Hormonin) is a combination pharmaceutical medication produced by Shire which contains the estrogens estradiol (0.3 or 0.6 mg), estrone (0.7 or 1.4 mg), and estriol (0.135 or 0.27 mg) in a singl ...
*
Estrone/progesterone
*
Estrogenic substances
Estrogenic substances, also referred to as natural estrogens and sold under the brand name Amniotin among others, is an estrogen medication which was marketed in the 1930s and 1940s and is no longer available. It was a purified extract of anima ...
References
Further reading
*
*
{{Estrogen receptor modulators
Abandoned drugs
Phenols
Sterols
Estranes
Estrogens
Ketones
Prodrugs