Pregnane

Pregnane
Names
	IUPAC name 5ξ-Pregnane
	Systematic IUPAC name (1S,3aS,3bS,5aΞ,9aS,9bS,11aR)-1-Ethyl-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
CAS Number	481-26-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:8386 ;
ChemSpider	5256760 ;
PubChem CID	6857422;
UNII	10Z78HHV4C ;
	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 Key: JWMFYGXQPXQEEM-WZBAXQLOSA-N ; 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).
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	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.

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 page: Biology:Pregnene

Cortisone

Pregnenes have a double bond. Examples include:

Cortisone
Hydrocortisone
Progesterone

Pregnadienes

Main page: Biology:Pregnadiene

Cyproterone acetate

Pregnadienes have two double bonds. Examples include:

Cyproterone acetate
Danazol
Fluocinonide

References

↑ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. pp. 1530. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

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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[1] International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. pp. 1530. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

v t e Steroid classification
C₁₇	Gonane
C₁₈	Estrane: Dehydrogenated: Estrene Estradiene Estratriene; Substituted: Estratrienolone Estratrienediol Estratrienetriol
C₁₉	Androstane: Dehydrogenated: Androstene Androstadiene Androstatriene; Substituted: Androstanol Androstenol Androstanone Androstenone Androstanediol Androstenediol Androstanedione Androstenedione Androstenetrione Androstanolone Androstenolone Androstadienol Androstadienone; Etiocholane
C₂₀	19-Norpregnane
C₂₁	Pregnane: Dehydrogenated: Pregnene Pregnadiene Pregnatriene; Substituted: Pregnanediol Pregnanetriol Pregnenediol Pregnanedione Pregnenedione 5α-Pregnane 5β-Pregnane
C₂₃	Cardanolide
C₂₄	Cholane Bile acid
C₂₇	Cholestane
Functional group	17-Ketosteroid Hydroxysteroid Halogenated steroid
Elements removed	Norsteroid Secosteroid
Elements replaced	Azasteroid