Dimethandrolone buciclate

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

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]

See also

References

  1. 1 2 3 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. 1 2 3 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. 1 2 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. 1 2 3 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. 1 2 3 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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