Pregnane

Pregnane

Names
IUPAC names (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
CompTox Dashboard (EPA)	DTXSID10425881
InChI InChI=1S/C21H36/c1-4-15-9-11-18-17-10-8-16-7-5-6-13-20(16,2)19(17)12-14-21(15,18)3/h15-19H,4-14H2,1-3H3/t15-,16?,17-,18-,19-,20-,21+/m0/s1 Y Key: JWMFYGXQPXQEEM-WZBAXQLOSA-N Y InChI=1/C21H36/c1-4-15-9-11-18-17-10-8-16-7-5-6-13-20(16,2)19(17)12-14-21(15,18)3/h15-19H,4-14H2,1-3H3/t15-,16?,17-,18-,19-,20-,21+/m0/s1 Key: JWMFYGXQPXQEEM-WZBAXQLOBZ
SMILES C41CCCC[C@@]1([C@@H]3[C@H]([C@@H]2CC[C@@H]([C@@]2(C)CC3)CC)CC4)C
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 YN ?) Infobox references

Pregnane is, 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).

5β-Pregnane is the parent of the progesterones, pregnane alcohols, ketones, and several adrenocortical hormones and is found largely in urine as a metabolic product of 5β-pregnane compounds.

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

• Pregnanedione
• Pregnanediol
• Androstane
• Estrane

External links

• Pregnanes at the U.S. 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