Dimethandrolone buciclate

Dimethandrolone buciclate

Clinical data
Routes of administration	Intramuscular injection
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
Synonyms	CDB-4386A; 7α,11β-Dimethyl-19-nortestosterone 17β-buciclate
Chemical and physical data
Formula	C31H48O3
Molar mass	468.7110 g/mol
3D model (Jmol)	Interactive image
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 19-nortestosterone (nandrolone) that 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

• 11β-Methyl-19-nortestosterone
• 11β-Methyl-19-nortestosterone dodecylcarbonate
• Dimethandrolone dodecylcarbonate
• Dimethandrolone undecanoate
• Nandrolone cyclotate
• Testosterone buciclate
• Testosterone undecanoate
• Trestolone acetate

References

1. Blye, Richard, and Hyun Kim. "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." U.S. Patent Application No. 10/260,854.
2. Blye, Richard, and Hyun Kim. "Method of making and using 7alpha, 11beta-dimethyl-17beta-hydroxyestr-4-en-3-one 17-undecanoate." U.S. Patent Application No. 11/040,964.
3. Blye, Richard P., et al. "Methods of making, using and pharmaceutical formulations comprising 7α, 11β-dimethyl-17β-hydroxyestra-4, 14-dien-3-one and 17 esters thereof." U.S. Patent No. 7,196,074. 27 Mar. 2007.
4. Blye, Richard P., and Hyun K. Kim. "Method of making and using 7alpha, 11beta-dimethyl-17beta-hydroxyestr-4-en-3-one 17-undecanoate." U.S. Patent Application No. 12/184,600.
5. Brown, A.E.; Sorbera, L.A. (2013). "Therapeutic targets for male contraception". Drugs of the Future. 38 (7): 499. doi:10.1358/dof.2013.038.07.1980494. ISSN 0377-8282.