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Androstane

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Androstane
Names
IUPAC name 5ξ-Androstane
Systematic IUPAC name (3aS,3bS,5aΞ,9aS,9bS,11aS)-9a,11a-Dimethylhexadecahydro-1H-cyclopentaphenanthrene
Other names Etioallocholane; 10β,13β-Dimethylgonane
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: QZLYKIGBANMMBK-FZFXZXLVSA-N
SMILES
  • C12(CCC2)()3()CCC4()CCCC4(C)3()CC1
  • C3C1CCCC1(2CC4((2C3)CCC4)C)C
Properties
Chemical formula C19H32
Molar mass 260.465 g·mol
Density 0.95 g/ml
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

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

Pharmacology

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

Androstanes

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

See also: List of androstanes


See also

References

  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
Androgen receptor modulators
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens and anabolic steroids
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