|Oral, intramuscular injection|
|Synonyms||Dimethandrolone undecylate; CDB-4521; 7α,11β-Dimethyl-19-nortestosterone 17β-undecanoate; 7α,11β-Dimethylestr-4-en-17β-ol-3-one 17β-undecanoate|
|Chemical and physical data|
|Molar mass||470.7269 g/mol|
|3D model (Jmol)||Interactive image|
Dimethandrolone undecanoate (DMAU) (developmental code name CDB-4521), or dimethandrolone undecylate, also known as 7α,11β-dimethyl-19-nortestosterone 17β-undecanoate, is a synthetic, orally active anabolic-androgenic steroid (AAS) and a derivative of 19-nortestosterone (nandrolone) that was developed by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development and has not been marketed at this time. It is an androgen ester – specifically, the C17β undecanoate ester of dimethandrolone (7α,11β-dimethyl-19-nortestosterone) – and acts as a prodrug of dimethandrolone in the body. DMAU is or was under development as a potential male contraceptive.
A pharmacokinetic study of DMAU in men found that only 2 to 3% of the drug was hydrolyzed into dimethandrolone when it was administered orally in the form of powder in capsules. In contrast, hydrolysis of testosterone undecanoate into testosterone is rapid and appears to be complete. The difference in conversion efficiency with DMAU relative to testosterone undecanoate is attributed to steric hindrance in DMAU caused by its additional C7α and C11β methyl groups. Although the hydrolysis of DMAU into dimethandrolone was very limited, it was still sufficient to produce dose-dependent biological effects at the dosages assessed, including reversible suppression of luteinizing hormone (LH) and testosterone levels. A subsequent pharmacokinetic study found that the conversion of DMAU into dimethandrolone was improved when the drug was delivered orally in castor oil/benzyl benzoate or a self-emulsifying drug delivery system contained in capsules as opposed to powder in capsules.
Unlike testosterone but similarly to 17α-alkyated AAS like methyltestosterone (17α-methyltestosterone), DMAU has been found to produce some effects indicative of potential hepatotoxicity when it was administered orally to animals. However, it is noteworthy that the effects were significantly less than those of methyltestosterone. Both DMAU and trestolone (7α-methyl-19-nortestosterone; MENT) showed potential signs of hepatotoxicity whereas 11β-methyl-19-nortestosterone 17β-dodecylcarbonate (11β-MNTDC) showed few to no such effects, suggesting that the C7α methyl group of DMAU and trestolone could be an important contributing factor to their hepatotoxic potential.
- Dimethandrolone buciclate
- Dimethandrolone dodecylcarbonate
- Nandrolone cyclotate
- Testosterone buciclate
- Trestolone acetate
- Roth MY (2012). "Male hormonal contraception". Virtual Mentor. 14 (2): 126–32. doi:10.1001/virtualmentor.2012.14.2.stas1-1202. PMC 4062384. PMID 23116954.
- Attardi BJ, Hild SA, Reel JR (2006). "Dimethandrolone undecanoate: a new potent orally active androgen with progestational activity". Endocrinology. 147 (6): 3016–26. doi:10.1210/en.2005-1524. PMID 16497801.
- Surampudi P, Page ST, Swerdloff RS, Nya-Ngatchou JJ, Liu PY, Amory JK, Leung A, Hull L, Blithe DL, Woo J, Bremner WJ, Wang C (2014). "Single, escalating dose pharmacokinetics, safety and food effects of a new oral androgen dimethandrolone undecanoate in man: a prototype oral male hormonal contraceptive". Andrology. 2 (4): 579–87. doi:10.1111/j.2047-2927.2014.00216.x. PMID 24789057.
- Attardi BJ, Engbring JA, Gropp D, Hild SA (2011). "Development of dimethandrolone 17beta-undecanoate (DMAU) as an oral male hormonal contraceptive: induction of infertility and recovery of fertility in adult male rabbits". J. Androl. 32 (5): 530–40. doi:10.2164/jandrol.110.011817. PMID 21164142.
- Ayoub, R. J., Page, S. T., Swerdloff, R. S., Liu, P. Y., Amory, J. K., Leung, A., ... & Wang, C. (2015) SAT-121: Comparison of the Pharmacokinetics (PK) and Safety of Three Oral Formulations of Dimethandrolone Undecanoate (DMAU): A Potential Male Oral Contraceptive. http://press.endocrine.org/doi/abs/10.1210/endo-meetings.2015.RE.11.SAT-121
- Hild SA, Attardi BJ, Koduri S, Till BA, Reel JR (2010). "Effects of synthetic androgens on liver function using the rabbit as a model". J. Androl. 31 (5): 472–81. doi:10.2164/jandrol.109.009365. PMC 2943539. PMID 20378929.