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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

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
Choong Y Ahn et al.
Drug metabolism and disposition: the biological fate of chemicals, 36(7), 1233-1241 (2008-04-02)
Protein expression of the hepatic CYP2E1 has been reported to be increased in diabetic rats. This enzyme is the primary metabolizer of chlorzoxazone (CZX) to 6-hydroxychlorzoxazone (OH-CZX). Although patients with liver cirrhosis have a higher prevalence of diabetes mellitus, there
Yang Li et al.
Pharmaceutical biology, 58(1), 695-700 (2020-07-17)
Lysionotin, a major extraction of Lysionotus pauciflorus Maxim (Gesneriaceae), has a variety of pharmacological properties commonly used in the treatment of lung disease. A study of lysionotin on the activity of human liver cytochrome P450 (CYP) enzymes can provide guidance
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