Dimethandrolone undecanoate

Dimethandrolone undecanoate
Clinical data
Other namesDimethandrolone undecylate; DMAU; CDB-4521; Dimethylnandrolone undecanoate; 7α,11β-Dimethyl-19-nortestosterone 17β-undecanoate; 7α,11β-Dimethylestr-4-en-17β-ol-3-one 17β-undecanoate
Routes of
administration		By mouth, intramuscular injection[1]
Drug classAndrogen; Anabolic steroid; Androgen ester; Progestogen
Identifiers
  • (1S,2R,9R,10R,11S,14S,15S,17S)-9,15,17-Trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl undecanoate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
Chemical and physical data
FormulaC31H47O3
Molar mass467.714 g·mol−1
3D model (JSmol)
  • O(C(CCCCCCCCCC)=O)[C@]1CC[C@]([H])2[C@@]([H])3[C@](C)CC4=CC(CC[C@]4([H])[C@@]3([H])[C@@](C)C[C@@]21C)=O
  • InChI=1S/C31H47O3/c1-5-6-7-8-9-10-11-12-13-28(33)34-27-17-16-26-30-21(2)18-23-19-24(32)14-15-25(23)29(30)22(3)20-31(26,27)4/h19,25-26,29-30H,5-18,20H2,1-4H3/t25-,26-,29+,30-,31-/m0/s1
  • Key:UITXCSFWQRCENT-SJDWCGKGSA-N

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.[2][3][4] It is taken by mouth, but can also be given by injection into muscle.[2][3][1]

Side effects of DMAU include mild weight gain and mild decreases in levels of HDL cholesterol.[5][6] It may also cause low estrogen levels and associated symptoms such as reduced sexual function and decreased bone mineral density.[7][8] DMAU is an AAS, and hence is an agonist of the androgen receptor, the biological target of androgens like testosterone.[2][3] It is also a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[2][3] Due to its androgenic and progestogenic activity, DMAU has antigonadotropic effects.[2][3] These effects result in reversible suppression of sperm production and are responsible for the contraceptive effects of DMAU in men.[2][3] The medication has no estrogenic activity.[7] DMAU is a prodrug of dimethandrolone.[2][3]

DMAU was first described in 2002.[9] It was developed by the Contraceptive Development Branch of the National Institute of Child Health and Human Development, an agency in the United States government.[2][3][4]

  1. ^ a b Roth MY (February 2012). "Male hormonal contraception". The Virtual Mentor. 14 (2): 126–132. doi:10.1001/virtualmentor.2012.14.2.stas1-1202. PMC 4062384. PMID 23116954.
  2. ^ a b c d e f g h Attardi BJ, Hild SA, Reel JR (June 2006). "Dimethandrolone undecanoate: a new potent orally active androgen with progestational activity". Endocrinology. 147 (6): 3016–3026. doi:10.1210/en.2005-1524. PMID 16497801. S2CID 45745191.
  3. ^ a b c d e f g h Surampudi P, Page ST, Swerdloff RS, Nya-Ngatchou JJ, Liu PY, Amory JK, et al. (July 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): 579–587. doi:10.1111/j.2047-2927.2014.00216.x. PMC 4069217. PMID 24789057.
  4. ^ a b 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". Journal of Andrology. 32 (5): 530–540. doi:10.2164/jandrol.110.011817. PMID 21164142.
  5. ^ Cite error: The named reference EndocrineSociety2018 was invoked but never defined (see the help page).
  6. ^ Rettner R (19 March 2018). "Male Birth Control Pill Blocks 'Sperm Hormones,' but Will It Work?". Live Science d.
  7. ^ a b Cite error: The named reference pmid18555683 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference pmid12788888 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference US20030069215 was invoked but never defined (see the help page).