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(Top) 1 Pharmacology 2 Androstanes 3 See also 4 References

Androstane

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Androstane
Names

IUPAC name 5ξ-Androstane
Systematic IUPAC name (3aS,3bS,5aΞ,9aS,9bS,11aS)-9a,11a-Dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene
Other names Etioallocholane; 10β,13β-Dimethylgonane
Identifiers
CAS Number	24887-75-0^Y 438-22-2 (5α)^N 438-23-3 (5β)^N
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:35509^Y
ChemSpider	5256872^Y
PubChem CID	94144
UNII	KT649U81FE (5α)^Y
CompTox Dashboard (EPA)	DTXSID40179587
InChI InChI=1S/C19H32/c1-18-11-5-7-16(18)15-9-8-14-6-3-4-12-19(14,2)17(15)10-13-18/h14-17H,3-13H2,1-2H3/t14?,15-,16-,17-,18-,19-/m0/s1^Y Key: QZLYKIGBANMMBK-FZFXZXLVSA-N^Y
SMILES C[C@@]12[C@](CCC2)([H])[C@]3([H])CCC4([H])CCCC[C@]4(C)[C@@]3([H])CC1 C3C1CCCC[C@@]1([C@H]2CC[C@]4([C@H]([C@@H]2C3)CCC4)C)C
Properties
Chemical formula	C₁₉H₃₂
Molar mass	260.465 g·mol⁻¹
Density	0.95 g/ml
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Androstane is a C19 steroidal hydrocarbon with a gonane core. Androstane can exist as either of two isomers, known as 5α-androstane and 5β-androstane.

5α-Androstane
5β-Androstane

Pharmacology

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5α-Androstane is reported to be effective as an androgen, in spite of having no oxygen containing functional groups.^[1]^[2]

Androstanes

[edit]

Androstanes are steroid derivatives with carbons present at positions 1 through 19.

References

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^ Wilson JD (1996). "Role of dihydrotestosterone in androgen action". Prostate Suppl. 6 (S6): 88–92. doi:10.1002/(SICI)1097-0045(1996)6+<88::AID-PROS17>3.0.CO;2-N. PMID 8630237. S2CID 41352599.

^ Segaloff A, Gabbard RB (1960). "5α-Androstane—An Androgenic Hydrocarbon". Endocrinology. 67 (6): 887–889. doi:10.1210/endo-67-6-887. ISSN 0013-7227. PMID 13749674.

v t e Steroid classification
C₁₇	Gonane
C₁₈	Estrane: Dehydrogenated: Estrene Estradiene Estratriene; Substituted: Estratrienolone Estratrienediol Estratrienetriol
C₁₉	Androstane: Dehydrogenated: Androstene Androstadiene Androstatriene; Substituted: Androstanol Androstenol Androstanone Androstenone Androstanediol Androstenediol Androstanedione Androstenedione Androstenetrione Androstanolone Androstenolone Androstadienol Androstadienone; Etiocholane
C₂₀	19-Norpregnane
C₂₁	Pregnane: Dehydrogenated: Pregnene Pregnadiene Pregnatriene; Substituted: Pregnanediol Pregnanetriol Pregnenediol Pregnanedione Pregnenedione 5α-Pregnane 5β-Pregnane
C₂₃	Cardanolide
C₂₄	Cholane Bile acid
C₂₇	Cholestane
Functional group	17-Ketosteroid Hydroxysteroid Halogenated steroid
Elements removed	Norsteroid Secosteroid
Elements replaced	Azasteroid