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Revision as of 09:49, 26 October 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChemSpiderID InChI1 InChIKey1 SMILES.← Previous edit		Latest revision as of 07:57, 18 August 2023 edit undoOAbot (talk | contribs)Bots440,440 editsm Open access bot: doi updated in citation with #oabot.
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	{{Unreferenced stub|auto=yes|date=December 2009}}
	{{Chembox		{{Chembox
	| verifiedrevid = 322374594		| verifiedrevid = 392964651
	| Name = 20-α-Dihydroprogesterone		| Name = 20α-Dihydroprogesterone
	| ImageFile = 20-alpha-dihydroprogesterone.svg		| ImageFile = 20-alpha-dihydroprogesterone.svg
	| ImageSize = 200px		| ImageSize = 225px
			| ImageAlt = Skeletal formula of 20α-dihydroprogesterone
	| IUPACName =
		⚫	| ImageFile1 = 20alpha-Dihydroprogesterone 3D ball.png
	| OtherNames =
			| ImageSize1 = 225px
			| ImageAlt1 = Ball-and-stick model of the 20α-dihydroprogesterone molecule
			| IUPACName = 20α-Hydroxypregn-4-en-3-one
			| SystematicName = (1''S'',3a''S'',3b''S'',9a''R'',9b''S'',11a''S'')-1--9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7''H''-cyclopentaphenanthren-7-one
			| OtherNames = 20α-DHP; 20α-Hydroxyprogesterone; 20α-OHP; Pregn-4-en-20α-ol-3-one
	| Section1 = {{Chembox Identifiers		| Section1 = {{Chembox Identifiers
	| ChemSpiderID = 83725		| ChemSpiderID = 83725
	| InChI1 = 1/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12-13,16-19,22H,4-11H2,1-3H3/t13-,16+,17-,18+,19+,20+,21-/m1/s1		| InChI1 = 1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12-13,16-19,22H,4-11H2,1-3H3/t13-,16-,17+,18-,19-,20-,21+/m0/s1
	| InChIKey1 = RWBRUCCWZPSBFC-SJOKZOANBK		| InChIKey1 = RWBRUCCWZPSBFC-RXRZZTMXSA-N
	| CASNo_Ref = {{cascite|correct|??}}		| CASNo_Ref = {{cascite|correct|yes}}
	| CASNo =		| CASNo = 145-14-2
	| PubChem = 8956		| PubChem = 8956
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| SMILES = O=C4\C=C2/(1CC3((CC31CC2)(O)C)C)(C)CC4
			| UNII = 45630A64AC
⚫	| MeSHName = 20-alpha-Dihydroprogesterone
			| EINECS = 205-649-5
		⚫	| SMILES = C(1CC21(CC32CCC4=CC(=O)CC34C)C)O
			| MeSHName = 20-alpha-Dihydroprogesterone
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
	| Formula = C<sub>21</sub>H<sub>32</sub>O<sub>2</sub>		| Formula = C<sub>21</sub>H<sub>32</sub>O<sub>2</sub>
	| MolarMass = 316.478 g/mol		| MolarMass = 316.478 g/mol
	| Appearance =		| Appearance =
	| Density =		| Density =
	| MeltingPt =		| MeltingPt =
	| BoilingPt =		| BoilingPt =
	}}		}}
	| Section3 = {{Chembox Hazards		| Section3 = {{Chembox Hazards
	| Solubility =		| MainHazards =
	| MainHazards =		| FlashPt =
	| FlashPt =		| AutoignitionPt =
	| Autoignition =
	}}		}}
	}}		}}
			'''20α-Dihydroprogesterone''' ('''20α-DHP'''), also known as '''20α-hydroxyprogesterone''' ('''20α-OHP'''), is a ], ] ].<ref name="pmid21182831">{{cite journal | vauthors = Beranič N, Gobec S, Rižner TL | title = Progestins as inhibitors of the human 20-ketosteroid reductases, AKR1C1 and AKR1C3 | journal = Chem. Biol. Interact. | volume = 191 | issue = 1–3 | pages = 227–33 | year = 2011 | pmid = 21182831 | doi = 10.1016/j.cbi.2010.12.012 }}</ref><ref name="PlantZeleznik2014">{{cite book|author1=Tony M. Plant|author2=Anthony J. Zeleznik|title=Knobil and Neill's Physiology of Reproduction: Two-Volume Set|url=https://books.google.com/books?id=I1ACBAAAQBAJ&pg=RA1-PA1205|date=15 November 2014|publisher=Academic Press|isbn=978-0-12-397769-4|pages=1–}}</ref><ref name="Darlington2009">{{cite book|author=Cynthia L. Darlington|title=The Female Brain|url=https://books.google.com/books?id=2CasCQAAQBAJ&pg=PA4|date=27 April 2009|publisher=CRC Press|isbn=978-1-4200-7745-2|pages=4–}}</ref> It is a ] of ], formed by the ]s (20α-HSDs) ], ], and ] and the ] (17β-HSD) ].<ref name="Legato2009">{{cite book|author=Marianne J. Legato|title=Principles of Gender-Specific Medicine|url=https://books.google.com/books?id=whb9hsUgZtwC&pg=PA617|date=29 October 2009|publisher=Academic Press|isbn=978-0-08-092150-1|pages=617–}}</ref><ref name="pmid24189185">{{cite journal | vauthors = Rižner TL, Penning TM | title = Role of aldo-keto reductase family 1 (AKR1) enzymes in human steroid metabolism | journal = Steroids | volume = 79 | pages = 49–63 | date = January 2014 | pmid = 24189185 | pmc = 3870468 | doi = 10.1016/j.steroids.2013.10.012 }}</ref> 20α-DHP can be transformed back into progesterone by 20α-HSDs and by the 17β-HSD ].<ref name="pmid11983494" /><ref name="PhungPaul2020">{{cite book|last1=Phung|first1=Jason|last2=Paul|first2=Jonathan|last3=Smith|first3=Roger|title=Maternal-Fetal and Neonatal Endocrinology|chapter=Maintenance of Pregnancy and Parturition|year=2020|pages=169–187|doi=10.1016/B978-0-12-814823-5.00013-1|isbn=9780128148235|s2cid=208410112 }}</ref> HSD17B2 is expressed in the human ] and ] among other tissues.<ref name="pmid7962560">{{cite journal | vauthors = Casey ML, MacDonald PC, Andersson S | title = 17 beta-Hydroxysteroid dehydrogenase type 2: chromosomal assignment and progestin regulation of gene expression in human endometrium | journal = J. Clin. Invest. | volume = 94 | issue = 5 | pages = 2135–41 | date = November 1994 | pmid = 7962560 | pmc = 294662 | doi = 10.1172/JCI117569 }}</ref><ref name="Ellenson2016">{{cite book|author=Lora Hedrick Ellenson|title=Molecular Genetics of Endometrial Carcinoma|url=https://books.google.com/books?id=wLqiDQAAQBAJ&pg=PA12|date=1 December 2016|publisher=Springer|isbn=978-3-319-43139-0|pages=12–}}</ref><ref name="pmid23410596">{{cite journal | vauthors = Byrns MC | title = Regulation of progesterone signaling during pregnancy: implications for the use of progestins for the prevention of preterm birth | journal = J. Steroid Biochem. Mol. Biol. | volume = 139 | pages = 173–81 | date = January 2014 | pmid = 23410596 | doi = 10.1016/j.jsbmb.2013.01.015 | s2cid = 23414730 }}</ref><ref name="PhungPaul2020" /> In animal studies, 20α-DHP has been found to be selectively taken up into and retained in target ]s such as the ], ], and ].<ref name="pmid11983494" />
	'''20-α-Dihydroprogesterone''' is a reduced form of ].
			20α-DHP has very low ] for the ] and is much less ] as a progestogen in comparison to progesterone, with about one-fifth of the relative progestogenic activity.<ref name="pmid21182831" /><ref name="PlantZeleznik2014" /><ref name="Darlington2009" /><ref name="Katzung2017">{{cite book|author=Bertram G. Katzung|title=Basic and Clinical Pharmacology 14th Edition|url=https://books.google.com/books?id=-W5ADwAAQBAJ|date=30 November 2017|publisher=McGraw-Hill Education|isbn=978-1-259-64116-9|page=728|quote=In addition to progesterone, 20α- and 20β-hydroxyprogesterone (20α- and 20β-hydroxy-4-pregnene-3-one) also are found. These compounds have about one-fifth the progestational activity of progesterone in humans and other species.}}</ref><ref name="pmid7078152">{{cite journal | vauthors = Ogle TF, Beyer BK | title = Steroid-binding specificity of the progesterone receptor from rat placenta | journal = J. Steroid Biochem. | volume = 16 | issue = 2 | pages = 147–50 | date = February 1982 | pmid = 7078152 | doi = 10.1016/0022-4731(82)90160-1 }}</ref><ref name="pmid11983494">{{cite journal | vauthors = Nowak FV | title = Distribution and metabolism of 20 alpha-hydroxylated progestins in the female rat | journal = J. Steroid Biochem. Mol. Biol. | volume = 80 | issue = 4–5 | pages = 469–79 | date = April 2002 | pmid = 11983494 | doi = 10.1016/S0960-0760(02)00039-0 | s2cid = 54366844 }}</ref><ref name="pmid13513735">{{cite journal | vauthors = Zander J, Forbes TR, Von Munstermann AM, Neher R | title = Delta 4-3-Ketopregnene-20 alpha-ol and delta 4-3-ketopregnene-20 beta-ol, two naturally occurring metabolites of progesterone; isolation, identification, biologic activity and concentration in human tissues | journal = J. Clin. Endocrinol. Metab. | volume = 18 | issue = 4 | pages = 337–53 | date = April 1958 | pmid = 13513735 | doi = 10.1210/jcem-18-4-337 | doi-access = free }}</ref> It has also been found to act as an ] and to inhibit the production of ] in ] tissue '']''.<ref name="pmid18751385">{{cite journal | vauthors = Pasqualini JR, Chetrite G | title = The anti-aromatase effect of progesterone and of its natural metabolites 20alpha- and 5alpha-dihydroprogesterone in the MCF-7aro breast cancer cell line | journal = Anticancer Res. | volume = 28 | issue = 4B | pages = 2129–33 | year = 2008 | pmid = 18751385 }}</ref>
			A single 200-mg oral dose of micronized progesterone has been found to result in peak levels of 20α-DHP of around 1&nbsp;ng/mL after 2&nbsp;hours.<ref name="pmid3327648">{{cite journal | vauthors = Sitruk-Ware R, Bricaire C, De Lignieres B, Yaneva H, Mauvais-Jarvis P | title = Oral micronized progesterone. Bioavailability pharmacokinetics, pharmacological and therapeutic implications--a review | journal = Contraception | volume = 36 | issue = 4 | pages = 373–402 | date = October 1987 | pmid = 3327648 | doi = 10.1016/0010-7824(87)90088-6 }}</ref> In another study however, peak levels of 20α-DHP were around 10&nbsp;ng/mL during therapy with 300&nbsp;mg/day oral micronized progesterone.<ref name="pmid3743792">{{cite journal | vauthors = Padwick ML, Endacott J, Matson C, Whitehead MI | title = Absorption and metabolism of oral progesterone when administered twice daily | journal = Fertil. Steril. | volume = 46 | issue = 3 | pages = 402–7 | date = September 1986 | pmid = 3743792 | doi = 10.1016/S0015-0282(16)49576-2 | doi-access = }}</ref> 20α-DHP is formed from progesterone in the ] and in target tissues such as the ].<ref name="pmid3743792" /> It appears to be more slowly eliminated than progesterone.<ref name="pmid3743792" />
			Levels of 5α-DHP have been quantified.<ref name="pmid26353176">{{cite journal | vauthors = Trabert B, Falk RT, Stanczyk FZ, McGlynn KA, Brinton LA, Xu X | title = Reproducibility of an assay to measure serum progesterone metabolites that may be related to breast cancer risk using liquid chromatography-tandem mass spectrometry | journal = Horm Mol Biol Clin Investig | volume = 23 | issue = 3 | pages = 79–84 | date = September 2015 | pmid = 26353176 | pmc = 4966666 | doi = 10.1515/hmbci-2015-0026 }}</ref>
	==See also==		==See also==
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			==References==
			{{Reflist}}
			{{Steroid hormones}}
⚫	{{DEFAULTSORT:Dihydroprogesterone, 20-Alpha-}}
			{{Progesterone receptor modulators}}
⚫	]
		⚫	{{DEFAULTSORT:Dihydroprogesterone, 20alpha}}
			]
	{{steroid-stub}}
			]
			]
		⚫	]
			]
			]
			]