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18-Hydroxy-11-deoxycorticosterone

18-Hydroxy-11-deoxycorticosterone
Names
IUPAC name
18,21-Dihydroxypregn-4-ene-3,20-dione
Systematic IUPAC name
(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
Other names
18,21-dihydroxy-4-pregnene-3,20-dione
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 206-834-3
MeSH 18-hydroxydeoxycorticosterone
  • InChI=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
    Key: VPJHREHKRNIYDB-TZGXILGRSA-N
  • C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4C(=O)CO)CO
Properties
C21H30O4
Molar mass 346.5
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.[1]

In rats, conversion of 11-deoxycorticosterone into 18-OH-DOC is catalyzed by the CYP11B3 enzyme.[2]

In humans, 18-OH-DOC is a weak mineralocorticoid.[3] It may be increased in 17α-hydroxylase (CYP17A1) deficiency,[4] in aldosterone synthase (CYP11B2) deficiency,[5] in primary aldosteronism, and may also indicate a histologic variant of the aldosteronoma.[4] Excessive secretion of 18-OH-DOC can cause mineralocorticoid excess syndrome, although these cases are very rare.[6]

References

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  1. ^ Fujii S, Momoi K, Okamoto M, Yamano T, Okada T, Terasawa T (June 1984). "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. doi:10.1021/bi00307a004. PMID 6466598.
  2. ^ Zhou MY, Gomez-Sanchez EP, Foecking MF, Gomez-Sanchez CE (October 1995). "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. doi:10.1016/0303-7207(95)03653-o. PMID 8674838. S2CID 53252461.
  3. ^ Williams GH, Braley LM, Underwood RH (July 1976). "The regulation of plasma 18-hydroxy 11-deoxycorticosterone in man". The Journal of Clinical Investigation. 58 (1): 221–9. doi:10.1172/JCI108453. PMC 333173. PMID 180059.
  4. ^ a b Ulick S (November 1976). "Adrenocortical factors in hypertension. I. Significance of 18-hydroxy-11-deoxycorticosterone". The American Journal of Cardiology. 38 (6): 814–24. doi:10.1016/0002-9149(76)90360-x. PMID 187051.
  5. ^ Riepe FG, Krone N, Peter M, Sippell WG, Partsch CJ (March 2003). "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. doi:10.1016/s1570-0232(02)00921-2. PMID 12554142.
  6. ^ Kawamura M, Owada M, Ino J, Sugawara T, Nakano T, Mochizuki I, Sakuma T, Segawa T, Motegi I, Sasano H (June 2003). "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. doi:10.2169/internalmedicine.42.507. PMID 12857050.
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