18-Hydroxycortisol

18-Hydroxycortisol
Names
	IUPAC name (11β,17α)-11,17,18,21-Tetrahydroxypregn-4-ene-3,20-dione
	Preferred IUPAC name (1S,3aS,3bS,9aR,9bS,10S,11aS)-1,10-Dihydroxy-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
Identifiers
CAS Number	144302-17-0 ; 86002-90-6 (non-specific) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:89455;
ChemSpider	17215950;
PubChem CID	102029;
UNII	T8YUY43659 ;
	InChI InChI=1S/C21H30O6/c1-19-6-4-13(24)8-12(19)2-3-14-15-5-7-21(27,17(26)10-22)20(15,11-23)9-16(25)18(14)19/h8,14-16,18,22-23,25,27H,2-7,9-11H2,1H3/t14-,15-,16-,18+,19-,20+,21+/m0/s1;
	SMILES C1(=O)CC[C@@]2([C@]3([C@H](C[C@@]4([C@@](CC[C@]4([C@@]3(CCC2=C1)[H])[H])(C(=O)CO)O)CO)O)[H])C;
Properties
Chemical formula	C21H30O6
Molar mass	378.465 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

18-Hydroxycortisol is an endogenous steroid.^[1]^[2]^[3]^[4]

Function

18-hydroxycortisol has been proposed as a biomarker for certain diseases. In humans, 18-hydroxycortisol has no biological activity on glucocorticoid or mineralocorticoid receptors. In healthy subjects, the biosynthesis of 18-hydroxycortisol is low. The highest synthesis of 18-hydroxycortisol was found in certain cases of hypertension like in type 1 familial hyperaldosteronism (glucocorticoid-curable hyperaldosteronism) and type 3 familial hyperaldosteronism, where the adrenal glands are enlarged up to six times their normal size. Increased synthesis is also found in patients with aldosterone-producing adenomas. ACTH stimulation test increases urinary excretion of 18-hydroxycortisol, and dexamethasone inhibits the excretion.^[1]

References

^ ^a ^b Lenders J, Williams T, Reincke M, Gomez-Sanchez C (January 2018). "18-Oxocortisol and 18-hydroxycortisol: is there clinical utility of these steroids?". European Journal of Endocrinology. 178 (1): R1–R9. doi:10.1530/EJE-17-0563. PMC 5705277. PMID 28904009.
^ Jin S, Wada N, Takahashi Y, Hui SP, Sakurai T, Fuda H, Takeda S, Fujikawa M, Yanagisawa K, Ikegawa S, Kurosawa T, Chiba H (September 2013). "Quantification of urinary 18-hydroxycortisol using LC-MS/MS". Annals of Clinical Biochemistry. 50 (Pt 5): 450–6. doi:10.1177/0004563213476272. PMID 23847032.
^ Mulatero P, di Cella SM, Monticone S, Schiavone D, Manzo M, Mengozzi G, Rabbia F, Terzolo M, Gomez-Sanchez EP, Gomez-Sanchez CE, Veglio F (March 2012). "18-hydroxycorticosterone, 18-hydroxycortisol, and 18-oxocortisol in the diagnosis of primary aldosteronism and its subtypes". The Journal of Clinical Endocrinology and Metabolism. 97 (3): 881–9. doi:10.1210/jc.2011-2384. PMID 22238407.
^ Chiba H (July 2010). "18-Hydroxycortisol, 18-oxocortisol, and 6beta-hydroxycortisol". Nihon Rinsho. Japanese Journal of Clinical Medicine (in Japanese). 68 Suppl 7: 339–43. PMID 20963880.

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[pmid28904009-1] Lenders J, Williams T, Reincke M, Gomez-Sanchez C (January 2018). "18-Oxocortisol and 18-hydroxycortisol: is there clinical utility of these steroids?". European Journal of Endocrinology. 178 (1): R1–R9. doi:10.1530/EJE-17-0563. PMC 5705277. PMID 28904009.

[pmid23847032-2] Jin S, Wada N, Takahashi Y, Hui SP, Sakurai T, Fuda H, Takeda S, Fujikawa M, Yanagisawa K, Ikegawa S, Kurosawa T, Chiba H (September 2013). "Quantification of urinary 18-hydroxycortisol using LC-MS/MS". Annals of Clinical Biochemistry. 50 (Pt 5): 450–6. doi:10.1177/0004563213476272. PMID 23847032.

[pmid22238407-3] Mulatero P, di Cella SM, Monticone S, Schiavone D, Manzo M, Mengozzi G, Rabbia F, Terzolo M, Gomez-Sanchez EP, Gomez-Sanchez CE, Veglio F (March 2012). "18-hydroxycorticosterone, 18-hydroxycortisol, and 18-oxocortisol in the diagnosis of primary aldosteronism and its subtypes". The Journal of Clinical Endocrinology and Metabolism. 97 (3): 881–9. doi:10.1210/jc.2011-2384. PMID 22238407.

[pmid20963880-4] Chiba H (July 2010). "18-Hydroxycortisol, 18-oxocortisol, and 6beta-hydroxycortisol". Nihon Rinsho. Japanese Journal of Clinical Medicine (in Japanese). 68 Suppl 7: 339–43. PMID 20963880.

[1]

[2]

[3]

[4]

Function

See also

References