18-Hydroxy-11-deoxycorticosterone

18-Hydroxy-11-deoxycorticosterone.svg 18,21-Dihydroxypregn-4-ene-3,20-dione (1S,3aS,3bR,9aR,9bS,11aR)-1-(Hydroxyacetyl)-11a-(hydroxymethyl)-9a-methyl-1,2,3,3a,3b,4,5,8,9,9a,9b,10,11,11a-tetradecahydro-7H-cyclopenta[a]phenanthren-7-one 18,21-dihydroxy-4-pregnene-3,20-dione 64970 C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4C(=O)CO)CO 379-68-0 58495 206-834-3 1S/C21H30O4/c1-20-8-6-14(24)10-13(20)2-3-15-16(20)7-9-21(12-23)17(15)4-5-18(21)19(25)11-22/h10,15-18,22-23H,2-9,11-12H2,1H3/t15-,16+,17+,18-,20+,21-/m1/s1 VPJHREHKRNIYDB-TZGXILGRSA-N 18-hydroxydeoxycorticosterone C21H30O4 346.5 18-Hydroxy-11-deoxycorticosterone (also known as 18-OH-DOC, 18,21-dihydroxyprogesterone, and 18,21-dihydroxypregn-4-ene-3,20-dione) is an endogenous steroid and a mineralocorticoid. It is a hydroxylated metabolite of 11-deoxycorticosterone. Fujii S, Momoi K, Okamoto M, Yamano T, Okada T, Terasawa T 18,19-Dihydroxydeoxycorticosterone, a new metabolite produced from 18-hydroxydeoxycorticosterone by cytochrome P-450(11) beta. Chemical synthesis and structural analysis by 1H NMR Biochemistry 23 12 2558–64 June 1984 6466598 10.1021/bi00307a004 In rats, conversion of 11-deoxycorticosterone into 18-OH-DOC is catalyzed by the CYP11B3 enzyme. Zhou MY, Gomez-Sanchez EP, Foecking MF, Gomez-Sanchez CE Cloning and expression of the rat adrenal cytochrome P-450 11B3 (CYP11B3) enzyme cDNA: preferential 18-hydroxylation over 11 beta-hydroxylation of DOC Molecular and Cellular Endocrinology 114 1–2 137–45 October 1995 8674838 10.1016/0303-7207(95)03653-o 53252461 In humans, 18-OH-DOC is a weak mineralocorticoid. Williams GH, Braley LM, Underwood RH The regulation of plasma 18-hydroxy 11-deoxycorticosterone in man The Journal of Clinical Investigation 58 1 221–9 July 1976 180059 333173 10.1172/JCI108453 It may be increased in 17α-hydroxylase (CYP17A1) deficiency, in aldosterone synthase (CYP11B2) deficiency, Riepe FG, Krone N, Peter M, Sippell WG, Partsch CJ Chromatographic system for the simultaneous measurement of plasma 18-hydroxy-11-deoxycorticosterone and 18-hydroxycorticosterone by radioimmunoassay: reference data for neonates and infants and its application in aldosterone-synthase deficiency Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences 785 2 293–301 March 2003 12554142 10.1016/s1570-0232(02)00921-2 in primary aldosteronism, and may also indicate a histologic variant of the aldosteronoma. Ulick S Adrenocortical factors in hypertension. I. Significance of 18-hydroxy-11-deoxycorticosterone The American Journal of Cardiology 38 6 814–24 November 1976 187051 10.1016/0002-9149(76)90360-x Excessive secretion of 18-OH-DOC can cause mineralocorticoid excess syndrome, although these cases are very rare. Kawamura M, Owada M, Ino J, Sugawara T, Nakano T, Mochizuki I, Sakuma T, Segawa T, Motegi I, Sasano H Effect of uni-adrenalectomy on blood pressure in a patient with excessive adrenal 18-hydroxy-11-deoxycorticosterone production bilaterally Internal Medicine (Tokyo, Japan) 42 6 507–12 June 2003 12857050 10.2169/internalmedicine.42.507 free References External links 18-hydroxydeoxycorticosterone Category:Mineralocorticoids Category:Steroid hormones