11β-Methyl-19-nortestosterone dodecylcarbonate

11β-Methyl-19-nortestosterone 17β-dodecylcarbonate (11β-MNTDC) (developmental code name CDB-4754) is a synthetic and orally active anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and has not been marketed for medical use at this time.[1][2][3][4] It is an androgen ester – specifically, the C17β dodecylcarbonate ester of 11β-methyl-19-nortestosterone (11β-MNT) – and acts as a prodrug of 11β-MNT in the body.[1][2][3][4]

11β-Methyl-19-nortestosterone dodecylcarbonate
Clinical data
Other names11β-MNTDC; CDB-4754
Routes of
administration		By mouth, intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester; Progestogen
Identifiers
IUPAC name
  • [(8R,9S,10R,11S,13S,14S,17S)-11,13-dimethyl-3-oxo-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl] dodecyl carbonate
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC32H52O4
Molar mass500.764 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCCCCCCCCOC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3[C@@H](C)C[C@]12C
InChI
  • InChI=1S/C32H52O4/c1-4-5-6-7-8-9-10-11-12-13-20-35-31(34)36-29-19-18-28-27-16-14-24-21-25(33)15-17-26(24)30(27)23(2)22-32(28,29)3/h21,23,26-30H,4-20,22H2,1-3H3/t23-,26-,27-,28-,29-,30+,32-/m0/s1
  • Key:JVTCGMMASZPYDR-UIRZMXPTSA-N

11β-MNTDC is under development as a birth control pill for men.[5][6][7] It has been described as the "sister compound" of dimethandrolone undecanoate, which is also under development as a birth control pill for men.[7][5]

Because 11β-MNTDC is not 5α-reduced, in contrast to testosterone, it may have less risk of scalp hair loss.[8]

See also

References
  1. Attardi BJ, Marck BT, Matsumoto AM, Koduri S, Hild SA (2011). "Long-term effects of dimethandrolone 17β-undecanoate and 11β-methyl-19-nortestosterone 17β-dodecylcarbonate on body composition, bone mineral density, serum gonadotropins, and androgenic/anabolic activity in castrated male rats". J. Androl. 32 (2): 183–92. doi:10.2164/jandrol.110.010371. PMID 20798389.
  2. Attardi BJ, Hild SA, Koduri S, Pham T, Pessaint L, Engbring J, Till B, Gropp D, Semon A, Reel JR (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". J. Steroid Biochem. Mol. Biol. 122 (4): 212–8. doi:10.1016/j.jsbmb.2010.06.009. PMC 2949447. PMID 20599615.
  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 2943539. PMID 20378929.
  4. Blye, Richard P., and Hyun K. Kim. "Nandrolone 17β-carbonates." U.S. Patent No. 7,820,642. 26 Oct. 2010.
  5. Thirumalai A, Page ST (January 2019). "Recent Developments in Male Contraception". Drugs. 79 (1): 11–20. doi:10.1007/s40265-018-1038-8. PMID 30588563. S2CID 56895132.
  6. "Second potential male birth control pill passes human safety tests".
  7. Yuen F, Thirumalai A, Pham C, et al. The novel androgen 11β-methyl-19-nortestosterone dodecylcarbonate (11β-MNTDC) effectively suppresses gonadotropins and testosterone in healthy men: a potential oral male hormonal contraceptive. Presented at: ENDO 2019; March 23-26, 2019; New Orleans, LA. Abstract SUN-LB042.
  8. Shapiro, Lawrence J.; Shapiro, Douglas B. (2018). Low Anabolic Profile in Assessing a Patient's Overall Hair Loss. pp. 687–698. doi:10.1007/978-4-431-56547-5_72. ISBN 978-4-431-56545-1.



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