Norgesterone, also known as norvinodrel or vinylestrenolone and sold under the brand name Vestalin, is a

progestin A progestogen, also referred to as a progestagen, gestagen, or gestogen, is a type of medication which produces effects similar to those of the natural product, natural female sex hormone progesterone in the body. A progestin is a ''synthetic co ...

medication which was formerly used in

birth control pill The combined oral contraceptive pill (COCP), often referred to as the birth control pill or colloquially as "the pill", is a type of birth control that is designed to be taken orally by women. The pill contains two important hormones: progest ...

s for women but is now no longer marketed. It was used in combination with the

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 ...

ethinylestradiol Ethinylestradiol (EE) is an estrogen medication which is used widely in birth control pills in combination with progestins. In the past, EE was widely used for various indications such as the treatment of menopausal symptoms, gynecological disord ...

. It is 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 ...

.Samaja, B. A., & Prandini, B. (1974). The influence of estrogenic and/or progestogenic treatment on some parameters of lipid metabolism: a controlled clinical study. ''Endokrinologie'', 63(1), 76-84. https://www.popline.org/node/492815 Norgesterone is a progestin, or a synthetic

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. ...

, and hence is 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

progesterone receptor The progesterone receptor (PR), also known as NR3C3 or nuclear receptor subfamily 3, group C, member 3, is a protein found inside cells. It is activated by the steroid hormone progesterone. In humans, PR is encoded by a single ''PGR'' gene resid ...

, the

biological target A biological target is anything within a living organism to which some other entity (like an endogenous ligand or a drug) is directed and/or binds, resulting in a change in its behavior or function. Examples of common classes of biological targets ...

of progestogens like

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 ...

. It has no

androgen An androgen (from Greek ''andr-'', the stem of the word meaning "man") is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This inc ...

ic activity. Norgesterone was first described in 1962. It is no longer available.

Medical uses

Norgesterone was used in combination with

s to prevent

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 ...

. It is no longer available.

Pharmacology

Pharmacodynamics

Norgesterone is a

, and hence is an

of the

. Unlike related progestins, it is virtually devoid of

ic activity in

animal Animals are multicellular, eukaryotic organisms in the Kingdom (biology), biological kingdom Animalia. With few exceptions, animals Heterotroph, consume organic material, Cellular respiration#Aerobic respiration, breathe oxygen, are Motilit ...

assay An assay is an investigative (analytic) procedure in laboratory medicine, mining, pharmacology, environmental biology and molecular biology for qualitatively assessing or quantitatively measuring the presence, amount, or functional activity of a ...

Chemistry

Norgesterone, also known as 17α-vinyl-δ⁵⁽¹⁰⁾-19-nortestosterone or as 17α-vinylestr-5(10)-en-17β-ol-3-one, is a synthetic

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 ...

and a

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. F ...

testosterone Testosterone is the primary sex hormone and anabolic steroid in males. In humans, testosterone plays a key role in the development of Male reproductive system, male reproductive tissues such as testes and prostate, as well as promoting secondar ...

and 19-nortestosterone. Analogues of norgesterone include

norvinisterone Norvinisterone, sold under the brand names Neoprogestin and Nor-Progestelea, is a progestin and androgen/ anabolic steroid (AAS) medication which was used in Europe but is now no longer marketed. It is taken by mouth. Norvinisterone is a proge ...

(17α-vinyl-19-nortestosterone) and

vinyltestosterone Vinyltestosterone (also known as 17α-vinyltestosterone, 17α-vinylandrost-4-en-17β-ol-3-one, and 17α-hydroxypregna-4,20-dien-3-one) is a synthetic anabolic–androgenic steroid (AAS) that was never marketed. However, two 19-nortestosterone der ...

(17α-vinyltestosterone).

History

Norgesterone was first described in 1962.

Society and culture

Generic names

''Norgesterone'' is the generic name of the drug and its . It has also been referred to as ''norvinodrel'', ''vinylestrenolone'', and ''vinylnoretynodrel''.

Brand names

Norgesterone was marketed in combination with

, an

, as a

under the brand name Vestalin.

Availability

Norgesterone is no longer marketed and hence is no longer available in any country.http://www.micromedexsolutions.com/micromedex2/

References

{{Progesterone receptor modulators Abandoned drugs Alkene derivatives Estranes Hormonal contraception Ketones Progestogens Vinyl compounds