6β-Hydroxycortisol

6β-Hydroxycortisol is an endogenous steroid. In humans, it is a metabolite of cortisol produced by cytochrome p450-3A monooxygenases, mainly, CYP3A4.[2][3][4][5] 6β-hydroxycortisol is used as a biomarker of CYP3A4 activity.[6] Drugs that induce CYP3A4 may accelerate cortisol clearance, by accelerating cortisol conversion to 6β-hydroxycortisol.[7][8]

6β-Hydroxycortisol
Names
IUPAC name
(6R,8S,9S,10R,11S,13S,14S,17R)-6,11,17-trihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
Other names
6-beta-hydroxycortisol, 6-beta-hydroxy-cortisol, 6beta-hydroxycortisol, 6beta-hydroxy-cortisol, 6β-OH-cortisol, 6beta-OH-cortisol, 6β-OHF, 6beta-OHF, 6β,11β,17,21-tetrahydroxypregn-4-ene-3,20-dione, (6β,11β)-6,11,17,21-tetrahydroxypregn-4-ene-3,20-dione, 6β,11β,17α,21-tetrahydroxypregn-4-ene-3,20-dione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C21H30O6/c1-19-5-3-11(23)7-14(19)15(24)8-12-13-4-6-21(27,17(26)10-22)20(13,2)9-16(25)18(12)19/h7,12-13,15-16,18,22,24-25,27H,3-6,8-10H2,1-2H3/t12-,13-,15+,16-,18+,19-,20-,21-/m0/s1
    Key: GNFTWPCIRXSCQF-UJXAPRPESA-N
  • InChI=1S/C21H30O6/c1-19-5-3-11(23)7-14(19)15(24)8-12-13-4-6-21(27,17(26)10-22)20(13,2)9-16(25)18(12)19/h7,12-13,15-16,18,22,24-25,27H,3-6,8-10H2,1-2H3/t12-,13-,15+,16-,18+,19-,20-,21-/m0/s1
  • C1[C@@]2([C@@]([C@@]3(C([C@@H]1O)=CC(CC3)=O)C)([C@H](C[C@@]4([C@@](CC[C@@]24[H])(O)C(CO)=O)C)O)[H])[H]
Properties
C21H30O6
Molar mass 378.46
Melting point 239-241°C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. "CAS Common Chemistry 6β-Hydroxycortisol Compound Properties".
  2. "PubChem 6beta-Hydroxycortisol compound summary".
  3. Luceri F, Fattori S, Luceri C, Zorn M, Mannaioni P, Messeri G (December 2001). "Gas chromatography-mass spectrometry measurement of 6beta-OH-cortisol/cortisol ratio in human urine: a specific marker of enzymatic induction". Clin Chem Lab Med. 39 (12): 1234–9. doi:10.1515/CCLM.2001.198. PMID 11798083. S2CID 12216877.
  4. Finken MJ, Andrews RC, Andrew R, Walker BR (September 1999). "Cortisol metabolism in healthy young adults: sexual dimorphism in activities of A-ring reductases, but not 11beta-hydroxysteroid dehydrogenases". J Clin Endocrinol Metab. 84 (9): 3316–21. doi:10.1210/jcem.84.9.6009. PMID 10487705.
  5. Huang FR, Zhou C, Zhang XY, Shen Y, Zhang HW, Wang YQ, Sun LN (October 2021). "Impact of CYP2C19 genotype on voriconazole exposure and effect of voriconazole on the activity of CYP3A in patients with haematological malignancies". Xenobiotica. 51 (10): 1199–1206. doi:10.1080/00498254.2021.1969481. PMID 34402388. S2CID 237150260.
  6. Lutz U, Bittner N, Ufer M, Lutz WK (January 2010). "Quantification of cortisol and 6 beta-hydroxycortisol in human urine by LC-MS/MS, and gender-specific evaluation of the metabolic ratio as biomarker of CYP3A activity". J Chromatogr B. 878 (1): 97–101. doi:10.1016/j.jchromb.2009.11.023. PMID 19959402.
  7. Aquinos BM, García Arabehety J, Canteros TM, de Miguel V, Scibona P, Fainstein-Day P (2021). "[Adrenal crisis associated with modafinil use]". Medicina (B Aires) (in Spanish). 81 (5): 846–849. PMID 34633961.
  8. Peng CC, Templeton I, Thummel KE, Davis C, Kunze KL, Isoherranen N (June 2011). "Evaluation of 6β-hydroxycortisol, 6β-hydroxycortisone, and a combination of the two as endogenous probes for inhibition of CYP3A4 in vivo". Clin Pharmacol Ther. 89 (6): 888–95. doi:10.1038/clpt.2011.53. PMC 3481835. PMID 21490593.
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