5α-Dihydroethisterone

5α-Dihydroethisterone
Clinical data
Other names	HE-3562; 5α-Dihydro-17α-Ethynyltestosterone; 17α-Ethynyl-DHT; 17α-Ethynyl-5α-androstan-17β-ol-3-one; 5α,17α-Pregn-20-yn-17β-ol-3-one; Ethynylandrostanolone
Drug class	Progestin; Progestogen; Androgen; Anabolic steroid
Identifiers
	IUPAC name (5S,8R,9S,10S,13S,14S,17R)-17-ethynyl-17-hydroxy-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-one;
CAS Number	13611-97-7;
PubChem CID	14887213;
ChemSpider	23317316;
ChEMBL	ChEMBL260202;
Chemical and physical data
Formula	C21H30O2
Molar mass	314.469 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C#C)O)C;
	InChI InChI=1S/C21H30O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,14,16-18,23H,5-13H2,2-3H3/t14-,16+,17-,18-,19-,20-,21-/m0/s1; Key:PVHMKHVQVIUQIP-JJFNZWTKSA-N;

5α-Dihydroethisterone (5α-DHET; developmental code name HE-3562) is an active metabolite of the formerly clinically used but now-discontinued progestin ethisterone and the experimental and never-marketed hormonal antineoplastic agent ethynylandrostanediol (HE-3235).^[1]^[2] Its formation from its parent drugs is catalyzed by 5α-reductase in tissues that express the enzyme in high amounts like the liver, skin, hair follicles, and prostate gland.^[1]^[2]^[3] 5α-DHET has significant affinity for steroid hormone receptors and may contribute importantly to the activities of its parent drugs.^[1]^[2]

^ ^a ^b ^c Lemus AE, Enríquez J, García GA, Grillasca I, Pérez-Palacios G (January 1997). "5alpha-reduction of norethisterone enhances its binding affinity for androgen receptors but diminishes its androgenic potency". J. Steroid Biochem. Mol. Biol. 60 (1–2): 121–9. doi:10.1016/S0960-0760(96)00172-0. PMID 9182866. S2CID 33771349.
^ ^a ^b ^c Ahlem C, Kennedy M, Page T, Bell D, Delorme E, Villegas S, Reading C, White S, Stickney D, Frincke J (February 2012). "17α-alkynyl 3α, 17β-androstanediol non-clinical and clinical pharmacology, pharmacokinetics and metabolism". Invest New Drugs. 30 (1): 59–78. doi:10.1007/s10637-010-9517-0. PMID 20814732. S2CID 24785562.
^ Dunaway G (1 April 2009). "Androgens and Antiandrogens". In Watts S, Faingold C, Dunaway G, Crespo L (eds.). Brody's Human Pharmacology - E-Book. Elsevier Health Sciences. pp. 468–. ISBN 978-0-323-07575-6.

[pmid9182866-1] Lemus AE, Enríquez J, García GA, Grillasca I, Pérez-Palacios G (January 1997). "5alpha-reduction of norethisterone enhances its binding affinity for androgen receptors but diminishes its androgenic potency". J. Steroid Biochem. Mol. Biol. 60 (1–2): 121–9. doi:10.1016/S0960-0760(96)00172-0. PMID 9182866. S2CID 33771349.

[pmid20814732-2] Ahlem C, Kennedy M, Page T, Bell D, Delorme E, Villegas S, Reading C, White S, Stickney D, Frincke J (February 2012). "17α-alkynyl 3α, 17β-androstanediol non-clinical and clinical pharmacology, pharmacokinetics and metabolism". Invest New Drugs. 30 (1): 59–78. doi:10.1007/s10637-010-9517-0. PMID 20814732. S2CID 24785562.

[WattsFaingold2009-3] Dunaway G (1 April 2009). "Androgens and Antiandrogens". In Watts S, Faingold C, Dunaway G, Crespo L (eds.). Brody's Human Pharmacology - E-Book. Elsevier Health Sciences. pp. 468–. ISBN 978-0-323-07575-6.

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