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C4397

Sigma-Aldrich

Chlorzoxazone

Synonym(s):

5-Chloro-2(3H)-benzoxazolone, 5-Chloro-2-hydroxybenzoxazole

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About This Item

Empirical Formula (Hill Notation):
C7H4ClNO2
CAS Number:
Molecular Weight:
169.57
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Assay

≥98% (TLC)

Quality Level

form

powder

color

white to off-white

mp

191-192 °C (lit.)

solubility

DMSO: 50 mg/mL, clear

originator

Johnson & Johnson

storage temp.

room temp

SMILES string

Clc1ccc2OC(=O)Nc2c1

InChI

1S/C7H4ClNO2/c8-4-1-2-6-5(3-4)9-7(10)11-6/h1-3H,(H,9,10)

InChI key

TZFWDZFKRBELIQ-UHFFFAOYSA-N

Gene Information

human ... KCNN4(3783)

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Application

Chlorzoxazone may be used:
  • as a calcium-activated potassium (KCa) channel activator in patch-clamp electrophysiology to test its effect on dendritic hyperexcitability
  • as a substrate for cytochrome P450 2E1 (CYP2E1) enzyme in cultured human hepatocytes
  • as a benzimidazolone compound to test its effect on epithelial sodium (Na+) transport

Biochem/physiol Actions

Chlorzoxazone inhibits the multisynaptic reflex arcs primarily in the spinal cord and brain subcortical areas. It is an activator of calcium activated potassium channels and may contribute to the aortic artery relaxation in mice. Chlorzoxazone also activates the calcium-activated potassium (KCa) channel and small conductance calcium-activated potassium channels (SK). It is metabolized by cytochrome P450 2E1 (CYP2E1) and serves as a probe for monitoring this enzyme function.
Chlorzoxazone is a skeletal muscle relaxant.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Potassium Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

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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B J Powers et al.
Archives of internal medicine, 146(6), 1183-1186 (1986-06-01)
A drug rechallenge proved chlorzoxazone to be hepatotoxic in a patient who had been treated with a combination of it and acetaminophen (Parafon Forte) for several months. Failure to demonstrate a toxic response to acetaminophen coupled with a dramatic response
Karina Alviña et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 30(21), 7258-7268 (2010-05-28)
Episodic ataxia type 2 (EA2) is a hereditary cerebellar ataxia associated with mutations in the P/Q-type voltage-gated calcium (Ca(2+)) channels. Therapeutic approaches for treatment of EA2 are very limited. Presently, the potassium (K(+)) channel blocker 4-aminopyridine (4-AP) constitutes the most
Sanjeev Kumar et al.
International journal of applied & basic medical research, 4(2), 101-105 (2014-08-22)
The fixed dose combinations (FDCs) of muscle relaxants, non-steroidal anti-inflammatory drugs and paracetamol are commonly prescribed in the treatment of acute lower backache. The present study was undertaken with the aim of comparing the efficacy and safety of FDCs of
F Woodward Hopf et al.
Biological psychiatry, 69(7), 618-624 (2011-01-05)
Alcoholism imposes a tremendous social and economic burden. There are relatively few pharmacological treatments for alcoholism, with only moderate efficacy, and there is considerable interest in identifying additional therapeutic options. Alcohol exposure alters SK-type potassium channel (SK) function in limbic
C A Syme et al.
American journal of physiology. Cell physiology, 278(3), C570-C581 (2000-03-11)
We previously characterized 1-ethyl-2-benzimidazolinone (1-EBIO), as well as the clinically useful benzoxazoles, chlorzoxazone (CZ), and zoxazolamine (ZOX), as pharmacological activators of the intermediate-conductance Ca(2+)-activated K(+) channel, hIK1. The mechanism of activation of hIK1, as well as the highly homologous small-conductance

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