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21-Deoxycortisone

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21-Deoxycortisone
Names
IUPAC name 17α-Hydroxypregn-4-ene-3,11,20-trione
Systematic IUPAC name (1R,3aS,3bS,9aR,9bS,11aS)-1-Acetyl-1-hydroxy-9a,11a-dimethyl-2,3,3a,3b,4,5,8,9,9a,9b,11,11a-dodecahydro-1H-cyclopentaphenanthrene-7,10-dione
Other names 21-Desoxycortisone; 11-Keto-17α-hydroxyprogesterone; 17α-Hydroxy-11-ketoprogesterone
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.015.947 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C21H28O4/c1-12(22)21(25)9-7-16-15-5-4-13-10-14(23)6-8-19(13,2)18(15)17(24)11-20(16,21)3/h10,15-16,18,25H,4-9,11H2,1-3H3/t15-,16-,18+,19-,20-,21-/m0/s1Key: PUKLDDOGISCFCP-JSQCKWNTSA-N
SMILES
  • CC(=O)1(CC21(CC(=O)32CCC4=CC(=O)CC34C)C)O
Properties
Chemical formula C21H28O4
Molar mass 344.451 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

21-Deoxycortisone, also known as 21-desoxycortisone, 11-keto-17α-hydroxyprogesterone, or 17α-hydroxypregn-4-ene-3,11,20-trione, is a naturally occurring, endogenous steroid and minor intermediate and metabolite in corticosteroid metabolism. It is related to 21-deoxycortisol (11β,17α-dihydroxyprogesterone) and is reversibly formed from it by 11β-hydroxysteroid dehydrogenase, analogously to the reversible formation of cortisone from cortisol. 21-Deoxycortisone can be transformed into cortisone by 21-hydroxylase.

See also

References

  1. Homma K, Hasegawa T, Takeshita E, Watanabe K, Anzo M, Toyoura T, Jinno K, Ohashi T, Hamajima T, Takahashi Y, Takahashi T, Matsuo N (2004). "Elevated urine pregnanetriolone definitively establishes the diagnosis of classical 21-hydroxylase deficiency in term and preterm neonates". J. Clin. Endocrinol. Metab. 89 (12): 6087–91. doi:10.1210/jc.2004-0473. PMID 15579762.
  2. ROSENFELD G, UNGAR F, DORFMAN RI, PINCUS G (1955). "Irradiation and adrenal steroidogenesis: steroid transformations by irradiated isolated perfused calf adrenals". Endocrinology. 56 (1): 24–9. doi:10.1210/endo-56-1-24. PMID 13220521.


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