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Androstane

From Wikipedia, the free encyclopedia
(Redirected from5α-Androstane)
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
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 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 checkY
    Key: QZLYKIGBANMMBK-FZFXZXLVSA-N checkY
  • 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
C19H32
Molar mass260.465 g·mol−1
Density0.95 g/ml
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Androstane is a C19steroidalhydrocarbon with agonane core. Androstane can exist as either of twoisomers, known as5α-androstane and5β-androstane.

  • 5α-Androstane
    5α-Androstane
  • 5β-Androstane
    5β-Androstane

Pharmacology

[edit]

5α-Androstane is reported to be effective as anandrogen, in spite of having nooxygen containingfunctional groups.[1][2]

Androstanes

[edit]

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

See also:List of androstanes


See also

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References

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  1. ^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.
  2. ^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.


Steroid classification
C17
C18
C19
C20
C21
C23
C24
C27
Functional group
Elements removed
Elements replaced
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
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