18-Hydroxycortisol

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18-Hydroxycortisol
Names
IUPAC name
11β,17α,18,21-Tetrahydroxypregn-4-ene-3,20-dione
Systematic 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
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 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
  • 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
C21H30O6
Molar mass 378.465 g·mol−1
Related compounds
Related compounds
 18-Oxocortisol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

18-Hydroxycortisol is an endogenous steroid,[1][2][3] a metabolite of cortisol.[4]

Clinical significance

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.[4]

Biosynthesis

In patients with familial hyperaldosteronism type 1, there is a genetic crossover between specific regions of the CYP11B1 and CYP11B2 genes. This crossover results in the expression of an additional gene in the zona fasciculata, which is regulated by ACTH. The additional gene plays a role in synthesizing 18-hydroxycortisol by 18-hydroxylation of cortisol.[4] This gene also plays a role in the biosynthesis of aldosterone and 18-oxocortisol.[4]

See also

References

  1. ^ Jin S, Wada N, Takahashi Y, Hui SP, Sakurai T, Fuda H, et al. (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. S2CID 32894100.
  2. ^ Mulatero P, di Cella SM, Monticone S, Schiavone D, Manzo M, Mengozzi G, et al. (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.
  3. ^ 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.
  4. ^ a b c d 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.
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