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UC148

Sigma-Aldrich

6-Hydroxychlorzoxazone

≥98% (HPLC), solid, chlorzoxazone metabolite

Synonym(s):

5-Chloro-6-hydroxy-2(3H)-benzoxazolone, 5-Chloro-6-hydroxybenzoxazone

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About This Item

Empirical Formula (Hill Notation):
C7H4ClNO3
CAS Number:
1750-45-4
Molecular Weight:
185.56
MDL number:
MFCD00143502
UNSPSC Code:
12161501
PubChem Substance ID:
24724641
NACRES:
NA.77

Product Name

6-Hydroxychlorzoxazone, ≥98% (HPLC)

Quality Level

200

assay

≥98% (HPLC)

form

solid

color

white to pink

solubility

methanol: soluble

storage temp.

2-8°C

SMILES string

Oc1cc2OC(=O)Nc2cc1Cl

InChI

1S/C7H4ClNO3/c8-3-1-4-6(2-5(3)10)12-7(11)9-4/h1-2,10H,(H,9,11)

InChI key

AGLXDWOTVQZHIQ-UHFFFAOYSA-N

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Application

6-Hydroxychlorzoxazone has been used for HPLC-based metabolic assays of chlorzoxazone.
6-hydroxy Chlorzoxazone has been used: as a reference standard to monitor substrate depletion or 6-hydroxy chlorzoxazone formation by cytochrome P450 family 2 subfamily E member 1 (CYP2E1)in recombinant human enzyme screening. 6-Hydroxychlorzoxazone has been used for high-performance liquid chromatography (HPLC)-based metabolic assays of chlorzoxazone.
CYP2E1 & 1A2 metabolite of chlorzoxazone.

Biochem/physiol Actions

6-hydroxy Chlorzoxazone is a novel metabolite of chlorzoxazone. It is formed by the hydroxylation of chlorzoxazone by cytochrome P450 family 2 subfamily E member 1 (CYP2E1) enzyme. The determination of formation and clearance of 6-hydroxychlorzoxazone is used as a reliable marker of CYP2E1 metabolic activity.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

6-Hydroxychlorzoxazone is soluble in methanol.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000154565
1385519V
1385519
065K3252
065K32521

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In vitro CYP/FMO Reaction Phenotyping
Optimization in Drug Discovery: In Vitro Methods, 137-169 (2014)
Drug Metabolism in Chronic Kidney Disease
Chronic Renal Disease, 1035-1051 (2020)
C B Eap et al.
Journal of chromatography. B, Biomedical sciences and applications, 705(1), 139-144 (1998-03-14)
A gas chromatographic-mass spectrometric method is presented which allows the determination of chlorzoxazone and 6-hydroxychlorzoxazone after derivatization with the reagent N-tert.-butyldimethylsilyl-N-methyltrifluoroacetamide. No interference was observed from endogenous compounds following the extraction of plasma samples from six different human subjects. The
Young Jin Moon et al.
Drug metabolism and disposition: the biological fate of chemicals, 31(6), 776-784 (2003-05-21)
The purpose of this study is to report the changes of CYP2E1, CYP1A2, CYP2B1/2, CYP2C11, CYP3A23, and CYP3A2 expression and pharmacokinetics and tissue distribution of chlorzoxazone (CZX) and 6-hydroxychlorzoxazone (OH-CZX) in rats with acute renal failure induced by uranyl nitrate
Hye W Baek et al.
Journal of pharmaceutical sciences, 95(11), 2452-2462 (2006-08-04)
Pharmacokinetic parameters of chlorzoxazone (CZX) and its main metabolite, 6-hydroxychlorzoxazone (OH-CZX), were compared after intravenous (20 mg/kg) and oral (50 mg/kg) administration of CZX in rat model of diabetes induced by alloxan (DMIA) or streptozotocin (DMIS), and their respective control
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