View source for Pregnane

{{No footnotes|date=April 2024}}
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 464213607
| ImageFile=Pregnane.svg
| ImageSize=
| ImageAlt=Skeletal formula of pregnane
| ImageFile1=Pregnane 3D ball.png
| ImageAlt1=Ball-and-stick model of the pregnane molecule
| IUPACName=5ξ-Pregnane<ref>{{cite book |author=[[International Union of Pure and Applied Chemistry]] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=[[Royal Society of Chemistry|The Royal Society of Chemistry]] |pages=1530 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
| SystematicName=(1''S'',3a''S'',3b''S'',5a''Ξ'',9a''S'',9b''S'',11a''R'')-1-Ethyl-9a,11a-dimethylhexadecahydro-1''H''-cyclopenta[''a'']phenanthrene
| OtherNames=
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5256760
| 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
| InChIKey = JWMFYGXQPXQEEM-WZBAXQLOBZ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JWMFYGXQPXQEEM-WZBAXQLOSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 481-26-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 10Z78HHV4C
| PubChem=6857422
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 8386
| SMILES = C41CCCC[C@@]1([C@@H]3[C@H]([C@@H]2CC[C@@H]([C@@]2(C)CC3)CC)CC4)C
}}
|Section2={{Chembox Properties
| Formula=C<sub>21</sub>H<sub>36</sub>
| MolarMass=288.511 g/mol
| Appearance=
| Density=0.926 g/ml
| MeltingPt=
| BoilingPt=
| Solubility=
  }}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
  }}
}}

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

5β-Pregnane is the parent of [[pregnanedione]]s, [[pregnanolone]]s, and [[pregnanediol]]s, and is found largely in [[urine]] as a [[metabolism|metabolic]] product of 5β-pregnane [[chemical compound|compound]]s.

==Pregnanes==
[[Image:Steroid numbering.svg|thumb|260px|[[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: [[pregnene]]s and [[pregnadiene]]s. Another class is [[pregnatriene]]s.

==Pregnenes==
{{main|Pregnene}}
[[Image:Cortisone structure.png|thumb|260px|[[Cortisone]]]]

Pregnenes have a [[double bond]]. Examples include:
* [[Cortisone]]
* [[Hydrocortisone]]
* [[Progesterone]]

==Pregnadienes==
{{main|Pregnadiene}}
[[Image:Cyproterone_acetate.svg|thumb|260px|[[Cyproterone acetate]]]]

Pregnadienes have two [[double bond]]s. Examples include:
* [[Cyproterone acetate]]
* [[Danazol]]
* [[Fluocinonide]]

==See also==
* [[5β-Pregnane]]
* [[Pregnanedione]]
* [[Pregnanediol]]
* [[19-Norpregnane]]
* [[Androstane]]
* [[Estrane]]

==References==
{{Reflist|2}}

==External links==
* {{Commonscatinline}}
* {{MeshName|Pregnanes}}
* [https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=439513 PubChem]
* [https://web.archive.org/web/20110514155935/http://www.chem.qmul.ac.uk/iupac/sectionF/steroid/ster13.html Diagram at qmul.ac.uk]
* [http://cancerweb.ncl.ac.uk/cgi-bin/omd?pregnane Definition of Pregnane]
* [https://web.archive.org/web/20080618062909/http://users.rcn.com/jkimball.ma.ultranet/BiologyPages/P/Progesterone.html Progesterone Chemistry]
* [http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17026 Progesterone record in European Bioinformatics database]

{{Steroid classification}}

[[Category:Endocrinology]]
[[Category:Pregnanes| ]]


{{steroid-stub}}