11-Deoxycorticosterone

11-Deoxycorticosterone
Names
IUPAC name
21-Hydroxypregn-4-ene-3,20-dione
Systematic IUPAC name
(1S,3aS,3bS,9aR,9bS,11aS)-1-(Hydroxyacetyl)-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
Deoxycorticosterone; Desoxycortone; Deoxycortone; Cortexone; 21-Hydroxyprogesterone; 21-Hydroxy-4-pregnene-3,20-dione; Reichstein's substance Q; Kendall's desoxy compound B; NSC-11319
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.543 Edit this at Wikidata
UNII
  • InChI=1S/C21H30O3/c1-20-9-7-14(23)11-13(20)3-4-15-16-5-6-18(19(24)12-22)21(16,2)10-8-17(15)20/h11,15-18,22H,3-10,12H2,1-2H3/t15-,16-,17-,18+,20-,21-/m0/s1
    Key: ZESRJSPZRDMNHY-YFWFAHHUSA-N
  • O=C4\C=C2/[C@]([C@H]1CC[C@@]3([C@@H](C(=O)CO)CC[C@H]3[C@@H]1CC2)C)(C)CC4
Properties
C21H30O3
Molar mass 330.461 g/mol
Pharmacology
H02AA03 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

11-Deoxycorticosterone (DOC), or simply deoxycorticosterone, also known as 21-hydroxyprogesterone, as well as desoxycortone (INN), deoxycortone, and cortexone,[1][2] is a steroid hormone produced by the adrenal gland that possesses mineralocorticoid activity and acts as a precursor to aldosterone.[3] It is an active (Na+-retaining) mineralocorticoid.[4] As its names indicate, 11-deoxycorticosterone can be understood as the 21-hydroxy-variant of progesterone or as the 11-deoxy-variant of corticosterone.

DOCA is the abbreviation for the ester 11-deoxycorticosterone acetate.[5]

  1. ^ Buckingham, MacDonald & Heilbron 1995.
  2. ^ Swiss Pharmaceutical Society 2011.
  3. ^ Costanzo 2014.
  4. ^ Harper's Illustrated Biochemistry 30th Edition
  5. ^ Wang D, Luo Y, Myakala K, Orlicky DJ, Dobrinskikh E, Wang X, Levi M (August 2017). "Serelaxin improves cardiac and renal function in DOCA-salt hypertensive rats". Scientific Reports. 7 (1): 9793. Bibcode:2017NatSR...7.9793W. doi:10.1038/s41598-017-09470-0. PMC 5574886. PMID 28851937.