18-Hydroxy-11-deoxycorticosterone

18-Hydroxy-11-deoxycorticosterone
Names
	IUPAC name (8R,9S,10R,13R,14S,17S)-17-(2-hydroxyacetyl)-13-(hydroxymethyl)-10-methyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
	Other names 18,21-dihydroxy-4-pregnene-3,20-dione
Identifiers
CAS Number	379-68-0;
3D model (JSmol)	Interactive image;
ChemSpider	58495;
EC Number	206-834-3;
MeSH	18-hydroxydeoxycorticosterone
PubChem CID	64970;
CompTox Dashboard (EPA)	DTXSID90958920 ;
	InChI 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;
	SMILES C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4C(=O)CO)CO;
Properties
Chemical formula	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).
	Infobox references

18-Hydroxy-11-deoxycorticosterone (18-OH-DOC), also known as 18,21-dihydroxyprogesterone, as well as 18,21-dihydroxypregn-4-ene-3,20-dione, is an endogenous steroid, 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

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.
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.
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.
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.
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.
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.

External links

18-hydroxydeoxycorticosterone at the US National Library of Medicine Medical Subject Headings (MeSH)

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[pmid6466598-1] 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.

[pmid180059-3] 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.

[pmid187051-4] 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.

[pmid12554142-5] 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.

[pmid12857050-6] 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.