Dimethandrolone buciclate

Dimethandrolone buciclate (developmental code name CDB-4386A), or dimethandrolone bucyclate, also known as 7α,11β-dimethyl-19-nortestosterone 17β-buciclate, is a synthetic 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 at this time.[1][2][3][4][5] It is an androgen ester – specifically, the C17β buciclate (4-butylcyclohexane-1-carboxylate) ester of dimethandrolone (7α,11β-dimethyl-19-nortestosterone) – and acts as a prodrug of dimethandrolone in the body.[1][2][3][4][5] Dimethandrolone buciclate is or was under investigation as a potential male contraceptive.[1][2][3][4][5]

Dimethandrolone buciclate
Clinical data
Other namesCDB-4386A; 7α,11β-Dimethyl-19-nortestosterone 17β-buciclate
Routes of
administration		Intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester; Progestogen
Identifiers
IUPAC name
  • (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 4-butylcyclohexane-1-carboxylate
PubChem CID
Chemical and physical data
FormulaC31H48O3
Molar mass468.722 g·mol−1
3D model (JSmol)
SMILES
  • [H][C@]12CCC(=O)C=C1C[C@@H](C)[C@H]1[C@@H]3CC[C@H](OC(=O)C4CCC(CCCC)CC4)[C@@]3(C)C[C@H](C)[C@H]21
InChI
  • InChI=1S/C31H48O3/c1-5-6-7-21-8-10-22(11-9-21)30(33)34-27-15-14-26-29-19(2)16-23-17-24(32)12-13-25(23)28(29)20(3)18-31(26,27)4/h17,19-22,25-29H,5-16,18H2,1-4H3/t19-,20+,21?,22?,25?,26+,27+,28-,29+,31?/m1/s1
  • Key:SQABEAOHFNPHNY-QFAUYDRKSA-N

See also

References
  1. US Abandoned 2003069215, Blye R, Kim H, "Methods of making and using 7a, 11b-dimethyl-17b-hydroxy-4-estren-3-one 17b-trans-4-n-butylcyclohexane carboxylate and 7a, 11b-dimethyl-17b-hydroxyestr-4-en-3-one 17-undecanoate.", published 10 April 2003, assigned to US Department of Health and Human Services
  2. US Abandoned 2005130944, Blye R, Kim H, "Method of making and using 7alpha, 11beta-dimethyl-17beta-hydroxyestr-4-en-3-one 17-undecanoate.", published 16 June 2005, assigned to US Department of Health and Human Services
  3. US Granted 7196074, Blye R, Kim H, "Methods of making, using and pharmaceutical formulations comprising 7α, 11β-dimethyl-17β-hydroxyestra-4, 14-dien-3-one and 17 esters thereof", issued 7 March 2007, assigned to US Department of Health and Human Services
  4. US Abandoned 2009023695, Blye R, Kim H, "Method of making and using 7alpha, 11beta-dimethyl-17beta-hydroxyestr-4-en-3-one 17-undecanoate.", published 22 January 2009, assigned to US Department of Health and Human Services
  5. Brown AE, Sorbera LA (2013). "Therapeutic targets for male contraception". Drugs of the Future. 38 (7): 499. doi:10.1358/dof.2013.038.07.1980494. ISSN 0377-8282.



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