C4397
Chlorzoxazone
Sinónimos:
5-Chloro-2(3H)-benzoxazolone, 5-Chloro-2-hydroxybenzoxazole
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About This Item
Fórmula empírica (notación de Hill):
C7H4ClNO2
Número CAS:
Peso molecular:
169.57
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
202-403-9
MDL number:
InChI key
TZFWDZFKRBELIQ-UHFFFAOYSA-N
InChI
1S/C7H4ClNO2/c8-4-1-2-6-5(3-4)9-7(10)11-6/h1-3H,(H,9,10)
SMILES string
Clc1ccc2OC(=O)Nc2c1
assay
≥98% (TLC)
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
Quality Level
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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Clase de almacenamiento
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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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
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
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
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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