Androstanolone enanthate

Androstanolone enanthate (brand name Anaboleen Depot), also known as stanolone enanthate or dihydrotestosterone heptanoate (DHTH), as well as 5α-androstan-17β-ol-3-one 17β-heptanoate, is a synthetic androgen and anabolic steroid and a dihydrotestosterone ester.[1][2] It is used as an injectable and acts as a prodrug of androstanolone (stanolone, dihydrotestosterone, DHT). The drug has been studied in and found to be effective in the treatment of gynecomastia in boys and adult men.[3][4][5] The pharmacology of androstanolone enanthate has been studied.[6][7]

Androstanolone enanthate
Clinical data
Trade namesAnaboleen Depot
Other namesStanolone enanthate; Dihydrotestosterone enanthate; DHT enanthate; Dihydrotestosterone heptanoate; DHTH; 5α-Androstan-17β-ol-3-one 17β-heptanoate
Routes of
administration		Intramuscular injection
Drug classAndrogen; Anabolic steroid; Androgen ester
Identifiers
IUPAC name
  • [(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl] heptanoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H42O3
Molar mass402.619 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CCC(=O)C4)C)C
InChI
  • InChI=1S/C26H42O3/c1-4-5-6-7-8-24(28)29-23-12-11-21-20-10-9-18-17-19(27)13-15-25(18,2)22(20)14-16-26(21,23)3/h18,20-23H,4-17H2,1-3H3/t18-,20-,21-,22-,23-,25-,26-/m0/s1
  • Key:DDYHAKNCTGGYOK-LVYWIKMTSA-N

See also

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 640–. ISBN 978-1-4757-2085-3.
  2. I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 261–. ISBN 978-94-011-4439-1.
  3. Swerdloff, Ronald S.; Wang, Christina (1998). "Dihydrotestosterone: A rationale for its use as a non-aromatizable androgen replacement therapeutic agent". Baillière's Clinical Endocrinology and Metabolism. 12 (3): 501–506. doi:10.1016/S0950-351X(98)80267-X. ISSN 0950-351X. PMID 10332569.
  4. Eberle AJ, Sparrow JT, Keenan BS (1986). "Treatment of persistent pubertal gynecomastia with dihydrotestosterone heptanoate". J. Pediatr. 109 (1): 144–9. doi:10.1016/s0022-3476(86)80596-0. PMID 3088241.
  5. Swerdloff, Ronald S.; Dudley, Robert E.; Page, Stephanie T.; Wang, Christina; Salameh, Wael A. (2017). "Dihydrotestosterone: Biochemistry, Physiology, and Clinical Implications of Elevated Blood Levels". Endocrine Reviews. 38 (3): 220–254. doi:10.1210/er.2016-1067. ISSN 0163-769X. PMC 6459338. PMID 28472278.
  6. Keenan, Bruce S.; Eberle, Andrea J.; Sparrow, James T.; Greger, Nancy G.; Panko, Walter B. (1987). "Dihydrotestosterone Heptanoate: Synthesis, Pharmacokinetics, and Effects on Hypothalamic-Pituitary-Testicular Function". The Journal of Clinical Endocrinology & Metabolism. 64 (3): 557–562. doi:10.1210/jcem-64-3-557. ISSN 0021-972X. PMID 3546348.
  7. Coutts SB, Kicman AT, Hurst DT, Cowan DA (November 1997). "Intramuscular administration of 5 alpha-dihydrotestosterone heptanoate: changes in urinary hormone profile". Clin. Chem. 43 (11): 2091–8. doi:10.1093/clinchem/43.11.2091. PMID 9365393.


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