Androstane

Androstane

Names
IUPAC name (8S,9S,10S,13S,14S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene
Other names Etioallocholane
Identifiers
CAS Number	24887-75-0 Y 438-22-2 (5α) N 438-23-3 (5β) N
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:35509 Y
ChemSpider	5256872 Y
PubChem	94144
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 InChI=1/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 Key: QZLYKIGBANMMBK-FZFXZXLVBX
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	260.46 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 steroid with a gonane core. Androstane can exist as either of two isomers, known as 5α-androstane and 5β-androstane.

• 

  5α-Androstane

• 

  5β-Androstane

Derivatives

Androstanes

• Androstanol
  • 3α,5α-Androstanol (5α-androstan-3α-ol) – an endogenous CAR antagonist
  • 3α,5β-Androstanol (5α-androstan-3β-ol) – an endogenous CAR antagonist
  • 5α,17-Androstanol (5α-androstan-17-ol) – an endogenous CAR antagonist
• Androstanone
  • 5α-Androstanone (5α-androstan-3-one)
• Androstanediol
  • 3α-Androstanediol (5α-androstane-3α,17β-diol) – an endogenous androgen, estrogen, and neurosteroid
  • 3β-Androstanediol (5α-androstane-3β,17β-diol) – an endogenous estrogen
• Androstanedione
  • 5α-Androstanedione (5α-androstane-3,17-dione)
  • 5β-Androstanedione (5β-androstane-3,17-dione)
• Androstanolone
  • Dihydrotestosterone (5α-androstan-17β-ol-3-one) – an endogenous androgen
  • 5β-Dihydrotestosterone (5β-androstan-17β-ol-3-one)
  • Androsterone (5α-androstan-3α-ol-17-one) – an endogenous androgen and neurosteroid
  • Epiandrosterone (5α-androstan-3β-ol-17-one) – an endogenous androgen
  • Etiocholanolone (5β-androstan-3α-ol-17-one) – an endogenous neurosteroid
  • Epietiocholanolone (5β-androstan-3β-ol-17-one)

Androstenes

• Androstenol
  • 3α,5α-Androstenol (5α-androst-16-en-3α-ol) – an endogenous pheromone, neurosteroid, and CAR antagonist
  • 3β,5α-Androstenol (5α-androst-16-en-3β-ol) – an endogenous pheromone
• Androstenone
  • 5α-Androstenone (5α-androst-16-en-3-one) – an endogenous pheromone
• Androstenediol
  • Δ⁵-Androstenediol (Δ⁵-androsten-3β,17β-diol) – an endogenous androgen, estrogen, and testosterone intermediate
  • Δ⁴-Androstenediol (Δ⁴-androsten-3β,17β-diol) – an androgen and testosterone prodrug
  • Δ¹-Androstenediol (Δ¹-androsten-3β,17β-diol) – an androgen and δ¹-testosterone prodrug
• Androstenedione
  • Δ⁴-Androstenedione (Δ⁴-androsten-3,17-dione) – an endogenous androgen and testosterone intermediate
  • Δ⁵-Androstenedione (Δ⁵-androsten-3,17-dione) – an androgen and testosterone prodrug
  • Δ¹-Androstenedione (Δ¹-androsten-3,17-dione) – an androgen and δ¹-testosterone prodrug
• Androstenetrione
  • δ⁴-Androstenetrione (δ⁴-androstene-3,6,17-trione) – an aromatase inhibitor
• Androstenolone
  • Testosterone (δ⁴-androsten-17β-ol-3-one) – an endogenous androgen
  • δ¹-Testosterone (δ¹-androsten-17β-ol-3-one) – an androgen
  • Epitestosterone (δ⁴-androsten-17α-ol-3-one) – an inactive steroid
  • Dehydroepiandrosterone (δ⁵-androsten-3β-ol-17-one) – an endogenous androgen, neurosteroid, agonist of PPARα, PXR, and CAR, and testosterone intermediate

Androstadienes

• Androstadienol
  • δ⁵-Androstadienol (δ⁵,16-androstadien-3β-ol) – an endogenous pheromone
  • δ⁴-Androstadienol (δ⁴,16-androstadien-3β-ol) – a synthetic pherine
• Androstadienone
  • δ⁴-Androstadienone (δ⁴,16-androstadien-3-one) – an endogenous pheromone

Anabolic steroids

Synthetic androgens and anabolic steroids are androstane derivatives.

Some progestins, such as ethisterone and dimethisterone, are also androstane derivatives.

See also

• Estrane
• Pregnane