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Dimethandrolone buciclate Other names CDB-4386A; 7α,11β-Dimethyl-19-nortestosterone 17β-buciclate Routes of administration Intramuscular injection Drug class Androgen ; Anabolic steroid ; Androgen ester ; Progestogen
(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
Formula C 31 H 48 O 3 Molar mass 468.7110 g/mol g·mol−1 3D model (JSmol )
[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=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
^ a b c 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.
^ a b c 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.
^ a b c 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.
^ a b c 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.
^ a b c 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 .
AR Tooltip Androgen receptor
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GPRC6A
PR Tooltip Progesterone receptor
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Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
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Tosagestin ; Anabolic–androgenic steroids: 11β-Methyl-19-nortestosterone
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RU-2309
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mPR Tooltip Membrane progesterone receptor (PAQR Tooltip Progestin and adipoQ receptor )