11-Deoxycortisol

11-Deoxycortisol
Cortodoxone chemical structure
Cortodoxone 3D ball molecule view
Names
IUPAC name
17α,21-Dihydroxypregn-4-ene-3,20-dione
Systematic IUPAC name
(1R,3aS,3bR,9aR,9bS,11aS)-1-Hydroxy-1-(2-hydroxy-1-oxoethyl)-9a,11a-dimethyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one
Other names
11-Deoxycortisol; 11-Deoxycortisone; Cortoxelone; 17α,21-Dihydroxyprogesterone; 11-Desoxycortisol; 11-Deoxyhydrocortisone; 11-Desoxyhydrocortisone; 17α-Hydroxy-11-deoxycorticosterone; Reichstein's Substance S; Compound S; Cortodoxone; Cortexolone,
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.279 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1 ☒N
    Key: WHBHBVVOGNECLV-OBQKJFGGSA-N ☒N
  • InChI=1/C21H30O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h11,15-17,22,25H,3-10,12H2,1-2H3/t15-,16+,17+,19+,20+,21+/m1/s1
    Key: WHBHBVVOGNECLV-OBQKJFGGBG
  • O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@](O)(C(=O)CO)CC[C@H]3[C@@H]1CC2)C)(C)CC4
Properties
C21H30O4
Molar mass 346.467 g·mol−1
Melting point 215 °C (419 °F; 488 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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11-Deoxycortisol, also known as cortodoxone (INN), cortexolone[1][2][3][4] as well as 17α,21-dihydroxyprogesterone or 17α,21-dihydroxypregn-4-ene-3,20-dione,[5] is an endogenous glucocorticoid steroid hormone, and a metabolic intermediate toward cortisol. It was first described by Tadeusz Reichstein in 1938 as Substance S,[6] thus has also been referred to as Reichstein's Substance S[5] or Compound S.[7][8]

  1. ^ Rosette C, Agan FJ, Rosette N, Mazzetti A, Moro L, Gerloni M (August 2020). "The dual androgen receptor and glucocorticoid receptor antagonist CB-03-10 as a potential treatment for tumors that have acquired GR-mediated resistance to AR blockade". Molecular Cancer Therapeutics. 19 (11): 2256–2266. doi:10.1158/1535-7163.MCT-19-1137. PMID 32847976. S2CID 221345484.
  2. ^ Iaderets VV, Andriushina VA, Bartoshevich IE, Domracheva AG, Novak MI, Stytsenko TS, Voĭshvillo NE (2007). "[A study of steroid hydroxylation activity of Curvularia lunata mycelium]". Prikladnaia Biokhimiia I Mikrobiologiia (in Russian). 43 (6): 695–700. PMID 18173113.
  3. ^ Manosroi J, Chisti Y, Manosroi A (2006). "Biotransformation of cortexolone to hydrocortisone by molds using a rapid color development assay". Prikladnaia Biokhimiia I Mikrobiologiia. 42 (5): 547–51. PMID 17066954.
  4. ^ Lisowska K, Długoński J (May 2003). "Concurrent corticosteroid and phenanthrene transformation by filamentous fungus Cunninghamella elegans". The Journal of Steroid Biochemistry and Molecular Biology. 85 (1): 63–9. doi:10.1016/s0960-0760(03)00136-5. PMID 12798358. S2CID 384672.
  5. ^ a b R.A. Hill, H.L.J. Makin, D.N. Kirk, G.M. Murphy (23 May 1991). Dictionary of Steroids. CRC Press. pp. 338–. ISBN 978-0-412-27060-4.
  6. ^ Reichstein T (1938). "Über Bestandteile der Nebennierenrinde. 21. Mitteilung. Die Konstitution der Substanzen R und S". Helvetica Chimica Acta. 21: 1490–1497. doi:10.1002/hlca.193802101183. Archived from the original on 10 October 2020. Retrieved 5 October 2020.
  7. ^ Wudy SA, Hartmann M, Homoki J (September 2002). "Determination of 11-deoxycortisol (Reichstein's compound S) in human plasma by clinical isotope dilution mass spectrometry using benchtop gas chromatography-mass selective detection". Steroids. 67 (10): 851–7. doi:10.1016/s0039-128x(02)00052-1. PMID 12231120. S2CID 29970823.
  8. ^ Berneis K, Staub JJ, Gessler A, Meier C, Girard J, Müller B (December 2002). "Combined stimulation of adrenocorticotropin and compound-S by single dose metyrapone test as an outpatient procedure to assess hypothalamic-pituitary-adrenal function". The Journal of Clinical Endocrinology and Metabolism. 87 (12): 5470–5. doi:10.1210/jc.2001-011959. PMID 12466339.