Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C7H4ClNO2 |
| Molecular Weight | 169.565 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
ClC1=CC2=C(OC(=O)N2)C=C1
InChI
InChIKey=TZFWDZFKRBELIQ-UHFFFAOYSA-N
InChI=1S/C7H4ClNO2/c8-4-1-2-6-5(3-4)9-7(10)11-6/h1-3H,(H,9,10)
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68002753
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68002753
Chlorzoxazone is a centrally acting central muscle relaxant with sedative properties. It is claimed to inhibit muscle spasm by exerting an effect primarily at the level of the spinal cord and subcortical areas of the brain where it inhibits multisynaptic reflex arcs involved in producing and maintaining skeletal muscle spasm of varied etiology. The clinical result is a reduction of the skeletal muscle spasm with relief of pain and increased mobility of the involved muscles. Chlorzoxazone is indicated as an adjunct to rest, physical therapy, and other measures for the relief of discomfort associated with acute, painful musculoskeletal conditions. The mode of action of this drug has not been clearly identified, but may be related to its sedative properties. Chlorzoxazone does not directly relax tense skeletal muscles in man.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL4305 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | CHLORZOXAZONE Approved UseINDICATIONS & USAGE SECTION Chlorzoxazone is indicated as an adjunct to rest, physical therapy, and other measures for the relief of discomfort associated with acute, painful musculoskeletal conditions. The mode of action of this drug has not been clearly identified, but may be related to its sedative properties. Chlorzoxazone does not directly relax tense skeletal muscles in man. Launch Date1988 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
15 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
12.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
5.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
3.45 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
6-HYDROXYCHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
5.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: QUERCETIN |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.14 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: QUERCETIN |
6-HYDROXYCHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
36.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6631711/ |
750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
43.5 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
32.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
15.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
9.86 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.95 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
6-HYDROXYCHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
16.69 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: QUERCETIN |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
0.64 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: QUERCETIN |
6-HYDROXYCHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
4084 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6631711/ |
750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
1.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
1.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
1.21 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.65 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28983678/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: QUERCETIN |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6631711/ |
750 mg single, oral dose: 750 mg route of administration: Oral experiment type: SINGLE co-administered: ACETAMINOPHEN |
CHLORZOXAZONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.9% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
4% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
3.2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12534643/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CHLORZOXAZONE serum | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
PubMed
| Title | Date | PubMed |
|---|---|---|
| ATP release triggered by activation of the Ca2+-activated K+ channel in human airway Calu-3 cells. | 2004-03 |
|
| Effects of cigarette smoking and carbon monoxide on chlorzoxazone and caffeine metabolism. | 2003-11 |
|
| Mechanism-based inhibition of human liver microsomal cytochrome P450 1A2 by zileuton, a 5-lipoxygenase inhibitor. | 2003-11 |
|
| GYKI-47261, a new AMPA [2-amino-3-(3-hydroxymethylisoxazole-4-yl)propionic acid] antagonist, is a CYP2E1 inducer. | 2003-11 |
|
| CYP2E1 regulation by benzene and other small organic chemicals in rat liver and peripheral lymphocytes. | 2003-09-15 |
|
| Simultaneous determination of aspirin and isosorbide 5-mononitrate in formulation by reversed phase high pressure liquid chromatography. | 2003-08-21 |
|
| Maintenance of liver functions in rat hepatocytes cultured as spheroids in a rotating wall vessel. | 2003-08-02 |
|
| Phorbol ester induces CYP2E1 in astrocytes, through a protein kinase C- and tyrosine kinase-dependent mechanism. | 2003-08 |
|
| Effects of glucose on the pharmacokinetics of intravenous chlorzoxazone in rats with acute renal failure induced by uranyl nitrate. | 2003-08 |
|
| CYP2E1 activity before and after weight loss in morbidly obese subjects with nonalcoholic fatty liver disease. | 2003-08 |
|
| Rates of metabolism of chlorzoxazone, dextromethorphan, 7-ethoxycoumarin, imipramine, quinidine, testosterone and verapamil by fresh and cryopreserved rat liver slices, and some comparisons with microsomes. | 2003-08 |
|
| Characterization of vectorial chloride transport pathways in the human pancreatic duct adenocarcinoma cell line HPAF. | 2003-08 |
|
| Differential inhibition of human cytochrome P450 enzymes by epsilon-viniferin, the dimer of resveratrol: comparison with resveratrol and polyphenols from alcoholized beverages. | 2003-07-18 |
|
| Effects of recombinant human growth hormone on the pharmacokinetics of intravenous chlorzoxazone in rats with acute renal failure induced by uranyl nitrate. | 2003-06-06 |
|
| Diterpene quinone tanshinone IIA selectively inhibits mouse and human cytochrome p4501A2. | 2003-06 |
|
| Functional characterization of three human cytochrome p450 2E1 variants with amino acid substitutions. | 2003-06 |
|
| How useful is the "cocktail approach" for evaluating human hepatic drug metabolizing capacity using cytochrome P450 phenotyping probes in vivo? | 2003-06 |
|
| Effects of acute renal failure on the pharmacokinetics of chlorzoxazone in rats. | 2003-06 |
|
| Cytochrome P450 expression and testosterone metabolism in the liver of deer. | 2003-05-01 |
|
| Construction and assessment of models of CYP2E1: predictions of metabolism from docking, molecular dynamics, and density functional theoretical calculations. | 2003-04-24 |
|
| Kinetic study of alkaline induced hydrolysis of the skeletal muscle relaxant chlorzoxazone using ratio spectra first derivative spectrophotometry. | 2003-04 |
|
| The cytochrome P-450 isoenzyme CYP2E1 in the biological processing of industrial chemicals: consequences for occupational and environmental medicine. | 2003-04 |
|
| Cytochrome P450 2E1 genotype and the susceptibility to antituberculosis drug-induced hepatitis. | 2003-04 |
|
| Lipopolysaccharide-mediated modulation of cytochromes P450 in Stat1 null mice. | 2003-04 |
|
| Isozyme-specific induction of low-dose aspirin on cytochrome P450 in healthy subjects. | 2003-03 |
|
| Pharmacokinetics of intravenous chlorzoxazone in rats with dehydration and rehydration: effects of food intakes. | 2003-03 |
|
| Hepatic cytochrome P450 2E1 activity in nondiabetic patients with nonalcoholic steatohepatitis. | 2003-03 |
|
| Metabolism of chloroform in the human liver and identification of the competent P450s. | 2003-03 |
|
| Study of the fragmentation mechanism of protonated 6-hydroxychlorzoxazone: application in simultaneous analysis of CYP2E1 activity with major human cytochrome P450s. | 2003-02-01 |
|
| Unexpected down-regulation of the hIK1 Ca2+-activated K+ channel by its opener 1-ethyl-2-benzimidazolinone in HaCaT keratinocytes. Inverse effects on cell growth and proliferation. | 2003-01-31 |
|
| Determination of 6-hydroxychlorzoxazone and chlorzoxazone in porcine microsome samples. | 2003-01-25 |
|
| Stimulatory effects of chlorzoxazone, a centrally acting muscle relaxant, on large conductance calcium-activated potassium channels in pituitary GH3 cells. | 2003-01-03 |
|
| Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes. | 2003-01-01 |
|
| Diabetes mellitus increases the in vivo activity of cytochrome P450 2E1 in humans. | 2003-01 |
|
| Validated HPLC method for determination of chlorzoxazone in human serum and its application in a clinical pharmacokinetic study. | 2002-12 |
|
| Potentiation of 2,2-dichloro-1,1,1-trifluoroethane (HCFC-123)-induced liver toxicity by ethanol in guinea-pigs. | 2002-12 |
|
| Evaluation of cytochrome P450 probe substrates commonly used by the pharmaceutical industry to study in vitro drug interactions. | 2002-12 |
|
| Conformational changes in nitric oxide synthases induced by chlorzoxazone and nitroindazoles: crystallographic and computational analyses of inhibitor potency. | 2002-11-26 |
|
| Monolithic silica rod liquid chromatography with ultraviolet or fluorescence detection for metabolite analysis of cytochrome P450 marker reactions. | 2002-11-25 |
|
| [Simultaneous determination of three probe drugs by reversed-phase high performance liquid chromatography]. | 2002-11 |
|
| Phenotype distribution and gender-related differences of CYP2E1 activity in a Chinese population. | 2002-11 |
|
| Inhibition of cytochrome P450 2E1 by propofol in human and porcine liver microsomes. | 2002-10-01 |
|
| Cytochrome P450 2E1 expression induces hepatocyte resistance to cell death from oxidative stress. | 2002-10 |
|
| Plasma levels of TNF-alpha and IL-6 are inversely related to cytochrome P450-dependent drug metabolism in patients with congestive heart failure. | 2002-10 |
|
| Metabolizing enzyme localization and activities in the first trimester human placenta: the effect of maternal and gestational age, smoking and alcohol consumption. | 2002-10 |
|
| Watercress has no Importance for the elimination of ethanol by CYP2E1 inhibition. | 2002-09 |
|
| Cytochrome P450 2E1 and 3A activities do not differ between Mexicans and European Americans. | 2002-09 |
|
| Cytochrome P450 phenotypic ratios for predicting herb-drug interactions in humans. | 2002-09 |
|
| Mechanism of aerobic transformation of carbon tetrachloride by poplar cells. | 2002 |
|
| Fondaparinux sodium is not metabolised in mammalian liver fractions and does not inhibit cytochrome P450-mediated metabolism of concomitant drugs. | 2002 |
Patents
Sample Use Guides
One tablet three or four times daily. If adequate response is not obtained with this dose, it may be increased to one and one-half tablets (750 mg) three or four times daily. As improvement occurs dosage can usually be reduced.
Route of Administration:
Oral
Chlorzoxazone did not affect the tension of the rat thoracic artery rings at rest, but relaxed the precontraction induced by 1 uM noradrenaline in an endothelium independent manner. Preincubation with chlorzoxazone also antagonized the contraction induced by 1 uM noradrenaline or 25 mM KCl.
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| Classification Tree | Code System | Code | ||
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LIVERTOX |
NBK548137
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NDF-RT |
N0000175737
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WHO-VATC |
QM03BB53
Created by
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WHO-ATC |
M03BB03
Created by
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WHO-VATC |
QM03BB03
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WHO-ATC |
M03BB53
Created by
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NDF-RT |
N0000175730
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WHO-ATC |
M03BB73
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NCI_THESAURUS |
C29696
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WHO-VATC |
QM03BB73
Created by
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202-403-9
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DTXSID9022813
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D002753
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H0DE420U8G
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H0DE420U8G
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2322
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95-25-0
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SUB06215MIG
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CHLORZOXAZONE
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2410
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CHEMBL1371
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3655
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748
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m3471
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1130505
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100000081896
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C28926
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626
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2733
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DB00356
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE INACTIVE (PARENT)
