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 taken by mouth, but can also be given by injection into muscle.

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
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)
SMILES
  • 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

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

DMAU was first described in 2002. 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.

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