Pregnane























































Pregnane

Skeletal formula of pregnane

Ball-and-stick model of the pregnane molecule
Names

IUPAC name
(8S,9S,10S,13R,14S,17S)-17-ethyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene

Identifiers

CAS Number

  • 24909-91-9 ☒N

3D model (JSmol)
  • Interactive image

ChEBI

  • CHEBI:8386 ☑Y

ChemSpider

  • 5256760 ☑Y


PubChem CID
  • 6857422




Properties

Chemical formula

 C21H36

Molar mass
 288.511 g/mol

Density
 0.926 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 ☑Y☒N ?)

Infobox references

Pregnane, also known as 17β-ethylandrostane or as 10β,13β-dimethyl-17β-ethylgonane, is a C21 steroid and, indirectly, a parent of progesterone. It is a parent hydrocarbon for two series of steroids stemming from 5α-pregnane (originally allopregnane) and 5β-pregnane (17β-ethyletiocholane). It has a gonane core.


5β-Pregnane is the parent of pregnanediones, pregnanolones, and pregnanediols, and is found largely in urine as a metabolic product of 5β-pregnane compounds.




Contents






  • 1 Pregnanes


  • 2 Pregnenes


  • 3 Pregnadienes


  • 4 See also


  • 5 References


  • 6 External links





Pregnanes





Steroid nomenclature: Pregnanes have carbons 1 through 21.


Pregnanes are steroid derivatives with carbons present at positions 1 through 21.


Most biologically significant pregnane derivatives fall into one of two groups: pregnenes and pregnadienes. Another class is pregnatrienes.



Pregnenes


Main article: Pregnene




Cortisone


Pregnenes have a double bond. Examples include:



  • Cortisone

  • Hydrocortisone

  • Progesterone



Pregnadienes


Main article: Pregnadiene




Cyproterone acetate


Pregnadienes have two double bonds. Examples include:



  • Cyproterone acetate

  • Danazol

  • Fluocinonide



See also



  • 5β-Pregnane

  • Pregnanedione

  • Pregnanediol

  • 19-Norpregnane

  • Androstane

  • Estrane



References





External links




  • Pregnanes at the US National Library of Medicine Medical Subject Headings (MeSH)

  • PubChem

  • Diagram at qmul.ac.uk

  • Definition of Pregnane

  • Progesterone Chemistry

  • Progesterone record in European Bioinformatics database














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