11β-Methyl-19-nortestosterone (11β-MNT) is a

synthetic Synthetic things are composed of multiple parts, often with the implication that they are artificial. In particular, 'synthetic' may refer to: Science * Synthetic chemical or compound, produced by the process of chemical synthesis * Synthetic o ...

and

orally active 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 ...

anabolic–androgenic steroid Anabolic steroids, also known more properly as anabolic–androgenic steroids (AAS), are steroidal androgens that include natural androgens like testosterone as well as synthetic androgens that are structurally related and have similar effects t ...

(AAS) 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 ...

of nandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and has not been marketed at this time. The C17β dodecyl

carbonate A carbonate is a salt of carbonic acid (H2CO3), characterized by the presence of the carbonate ion, a polyatomic ion with the formula . The word ''carbonate'' may also refer to a carbonate ester, an organic compound containing the carbonate g ...

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

of 11β-MNT, 11β-methyl-19-nortestosterone 17β-dodecylcarbonate (11β-MNTDC) (CDB-4754), 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 11β-MNT. Along with the closely related AAS

dimethandrolone Dimethandrolone (DMA), also known by its developmental code name CDB-1321, is an experimental androgen/anabolic steroid (AAS) and progestogen medication which is under investigation for potential clinical use. Dimethandrolone is an AAS, and he ...

(7α,11β-dimethyl-19-nortestosterone; CDB-1321) and its ester prodrug

dimethandrolone undecanoate Dimethandrolone undecanoate (DMAU), also known by its developmental code name CDB-4521, is an experimental androgen/ anabolic steroid (AAS) and progestogen medication which is under development as a potential birth control pill for men. It is t ...

(CDB-4521), 11β-MNT and 11β-MNTDC are under investigation as potential male contraceptives and to treat male hypogonadism.

Side effects

Pharmacology

Pharmacodynamics

11β-MNT does not undergo aromatization into the corresponding

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 ...

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...

11β-methylestradiol, and for this reason, has no potential for estrogenic side effects such as gynecomastia. In addition, unlike

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 ...

, 11β-MNT does not appear to undergo 5α-reduction into the corresponding 5α- dihydrogenated metabolite 5α-dihydro-11β-MNT (5α-DHMNT). This conclusion is based on the fact that 5α-DHMNT is 4 to 8 times as potent as 11β-MNT in terms of androgenicity 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 ...

bioassays, yet the co-administration of the

5α-reductase inhibitor 5α-Reductases, also known as 3-oxo-5α-steroid 4-dehydrogenases, are enzymes involved in steroid metabolism. They participate in three metabolic pathways: bile acid biosynthesis, androgen and estrogen metabolism. There are three isozymes of ...

dutasteride with 11β-MNT had no influence on its potency in assays using tissues that express 5α-reductase like the ventral prostate and seminal vesicles. Due to lack of potentiation by 5α-reductase in androgenic tissues like the

skin Skin is the layer of usually soft, flexible outer tissue covering the body of a vertebrate animal, with three main functions: protection, regulation, and sensation. Other cuticle, animal coverings, such as the arthropod exoskeleton, have diffe ...

hair follicle The hair follicle is an organ found in mammalian skin. It resides in the dermal layer of the skin and is made up of 20 different cell types, each with distinct functions. The hair follicle regulates hair growth via a complex interaction between h ...

s, and prostate gland, 11β-MNT may have a lower risk of certain side effects such as

oily skin The human skin is the outer covering of the body and is the largest organ of the integumentary system. The skin has up to seven layers of ectodermal tissue guarding muscles, bones, ligaments and internal organs. Human skin is similar to most ...

acne Acne, also known as ''acne vulgaris'', is a long-term Cutaneous condition, skin condition that occurs when Keratinocyte, dead skin cells and Sebum, oil from the skin clog hair follicles. Typical features of the condition include comedo, black ...

androgenic alopecia Pattern hair loss (also known as androgenetic alopecia (AGA)) is a hair loss condition that primarily affects the top and front of the scalp. In male-pattern hair loss (MPHL), the hair loss typically presents itself as either a receding front ha ...

(pattern hair loss),

prostate enlargement Benign prostatic hyperplasia (BPH), also called prostate enlargement, is a noncancerous increase in size of the prostate gland. Symptoms may include frequent urination, trouble starting to urinate, weak stream, inability to urinate, or loss o ...

, and

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 ...

than testosterone and certain other AAS. Similarly to nandrolone, dimethandrolone, and other 19-nortestosterone derivatives, 11β-MNT has been found to possess

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. ...

ic activity. Because of its dual activity as an AAS and progestogen, 11β-MNT may have greater

efficacy Efficacy is the ability to perform a task to a satisfactory or expected degree. The word comes from the same roots as ''effectiveness'', and it has often been used synonymously, although in pharmacology a pragmatic clinical trial#Efficacy versu ...

in suppression of

spermatogenesis Spermatogenesis is the process by which haploid spermatozoa develop from germ cells in the seminiferous tubules of the testis. This process starts with the mitotic division of the stem cells located close to the basement membrane of the tubule ...

and hence male fertility than pure AAS like testosterone. Oral 11β-MNT has shown little to no potential for hepatotoxicity in animals, similarly to testosterone but unlike 17α-alkylated AAS like

methyltestosterone Methyltestosterone, sold under the brand names Android, Metandren, and Testred among others, is an androgen and anabolic steroid (AAS) medication which is used in the treatment of low testosterone levels in men, delayed puberty in boys, at low ...

. The drug notably shows a much lower hepatotoxic potential than dimethandrolone and trestolone (7α-methyl-19-nortestosterone; MENT), which may have an increased risk due to their shared C7α methyl group (although a risk that is still significantly lower than that of 17α-alkylated AAS).

Chemistry

11β-MNT, or 11β-methyl-19-nortestosterone, also known as 11β-methylestr-4-en-17β-ol-3-one, is a

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 non-17α-alkylated

of nandrolone (19-nortestosterone).

References

{{DEFAULTSORT:Methyl-19-nortestosterone, 11β- Secondary alcohols Androgens and anabolic steroids Estranes Experimental drugs Contraception for males Enones Progestogens