Dimethandrolone undecanoate

Dimethandrolone undecanoate
Clinical data
Routes of
administration		 Oral, intramuscular injection[1]
Identifiers
Synonyms Dimethandrolone undecylate; CDB-4521; 7α,11β-Dimethyl-19-nortestosterone 17β-undecanoate; 7α,11β-Dimethylestr-4-en-17β-ol-3-one 17β-undecanoate
CAS Number 366472-45-9
Chemical and physical data
Formula C31H50O3
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.[2][3][4] 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.[2][3] DMAU is or was under development as a potential male contraceptive.[2][3]

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.[3] In contrast, hydrolysis of testosterone undecanoate into testosterone is rapid and appears to be complete.[3] 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.[3] 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.[3] 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.[5]

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.[6] However, it is noteworthy that the effects were significantly less than those of methyltestosterone.[6] 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.[6]

See also

References

  1. ↑ Roth MY (2012). "Male hormonal contraception". Virtual Mentor. 14 (2): 126–32. doi:10.1001/virtualmentor.2012.14.2.stas1-1202. PMC 4062384Freely accessible. PMID 23116954.
  2. 1 2 3 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.
  3. 1 2 3 4 5 6 7 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.
  4. ↑ 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.
  5. ↑ 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
  6. 1 2 3 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 2943539Freely accessible. PMID 20378929.


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