Dimethandrolone

This article is about a non-clinically used compound. For the experimental contraceptive, see Dimethandrolone undecanoate.
Dimethandrolone
Clinical data
Other namesCDB-1321; Dimethylnandrolone; 7α,11β-Dimethyl-19-nortestosterone; 7α,11β-Dimethylestr-4-en-17β-ol-3-one; 7α,11β-Dimethyl-19-norandrost-4-en-17β-ol-3-one
Routes of
administration		By mouth
Drug classAndrogen; Anabolic steroid; Progestogen
Identifiers
  • (7R,8R,9S,10R,11S,13S,14S,17S)-17-hydroxy-7,11,13-trimethyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H30O2
Molar mass302.458 g·mol−1
3D model (JSmol)
  • CC1CC2=CC(=O)CCC2C3C1C4CCC(C4(CC3C)C)O
  • InChI=1S/C20H30O2/c1-11-8-13-9-14(21)4-5-15(13)18-12(2)10-20(3)16(19(11)18)6-7-17(20)22/h9,11-12,15-19,22H,4-8,10H2,1-3H3/t11-,12+,15+,16+,17+,18-,19+,20+/m1/s1
  • Key:KVIKZOGGZHCGFH-RJMNTABLSA-N

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.[1][2][3]

Dimethandrolone is an AAS, and hence is an agonist of the androgen receptor, the biological target of androgens like testosterone.[1] 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.[1] Due to its androgenic and progestogenic activity, dimethandrolone has antigonadotropic effects.[1] It has no estrogenic activity.[1][4]

Dimethandrolone was first described in 1997.[5] 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.[1][6]

An ester and prodrug of dimethandrolone, dimethandrolone undecanoate (DMAU) (CDB-4521), is under development for potential use as a birth control pill for men and in androgen replacement therapy for men.[1][2][3][7]

  1. ^ a b c d e f g Attardi BJ, Hild SA, Reel JR (June 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. S2CID 45745191.
  2. ^ a b Attardi BJ, Hild SA, Koduri S, Pham T, Pessaint L, Engbring J, et al. (October 2010). "The potent synthetic androgens, dimethandrolone (7α,11β-dimethyl-19-nortestosterone) and 11β-methyl-19-nortestosterone, do not require 5α-reduction to exert their maximal androgenic effects". The Journal of Steroid Biochemistry and Molecular Biology. 122 (4): 212–8. doi:10.1016/j.jsbmb.2010.06.009. PMC 2949447. PMID 20599615.
  3. ^ a b Wang C, Swerdloff RS (November 2010). "Hormonal approaches to male contraception". Current Opinion in Urology. 20 (6): 520–4. doi:10.1097/MOU.0b013e32833f1b4a. PMC 3078035. PMID 20808223.
  4. ^ Cite error: The named reference pmid18555683 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference US5952319A was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference pmid21164142 was invoked but never defined (see the help page).
  7. ^ "Dimethandrolone undecanoate shows promise as a male birth control pill". Press Release. Endocrine Society. March 18, 2018.