Chlorzoxazone (CED0006658)

Record Information
Version1.0
Creation Date2016-05-22 03:38:53 UTC
Update Date2026-08-24 01:08:13 UTC
Accession NumberCHEM016630
Identification
Common NameChlorzoxazone
ClassSmall Molecule
Description
Chlorzoxazone is an organic compound with the chemical formula C7H4ClNO2 and an average molecular weight of 169.56 g/mol. Chlorzoxazone belongs to the benzoxazolones, a subclass of benzoxazoles within the organic compounds. In terms of pharmacological activity, it acts as an inhibitor of the protein target Calcium-activated potassium channel subunit alpha-1 (KCNMA1). The compound is utilized in healthcare, pharmaceuticals, and veterinary products as a muscle relaxant. Recorded exposure routes for chlorzoxazone include oral administration and the occlusive dressing technique. It has been identified in or released from 11 recorded sources across various categories. Within household cleaning and consumer products, it is found in tobacco smoke filters, perfumes within detergents and soaps, and non-electric simulated smoking devices. In the sector of electrical and electronic equipment, sources include electrodes, electric hearing aids, electrically stimulated smoking devices, communication cables or conductors, and conductors or conductive bodies characterised by the conductive materials, among two other sources.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
2-Hydroxy-5-chlorobenzoxazoleChEBI
5-Chloro-2(3H)-benzoxazoloneChEBI
5-Chloro-2-benzoxazolinoneChEBI
5-Chloro-2-benzoxazololChEBI
5-Chloro-2-benzoxazoloneChEBI
5-Chloro-2-hydroxybenzoxazoleChEBI
5-ChlorobenzoxazolidoneChEBI
5-Chlorobenzoxazolin-2-oneChEBI
ChlorzoxaneChEBI
ChlorzoxazonaChEBI
ChlorzoxazonumChEBI
ParaflexKegg
ChloroxazoneHMDB
ChlorzoxazonHMDB
McNeil brand OF chlorzoxazoneHMDB
Ortho brand OF chlorzoxazoneHMDB
Parafon forte DSCHMDB
ParafonHMDB
Chemical FormulaC7H4ClNO2
Average Molecular Mass169.565 g/mol
Monoisotopic Mass168.993 g/mol
CAS Registry Number95-25-0
IUPAC Name5-chloro-2,3-dihydro-1,3-benzoxazol-2-one
Traditional Namechlorzoxazone
SMILESClC1=CC2=C(OC(=O)N2)C=C1
InChI IdentifierInChI=1S/C7H4ClNO2/c8-4-1-2-6-5(3-4)9-7(10)11-6/h1-3H,(H,9,10)
InChI KeyTZFWDZFKRBELIQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoxazolones. These are organic compounds containing a benzene fused to an oxazole ring (a five-member aliphatic ring with three carbon atoms, one oxygen atom, and one nitrogen atom) bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxazoles
Sub ClassBenzoxazolones
Direct ParentBenzoxazolones
Alternative Parents
Substituents
  • Benzoxazolone
  • Aryl chloride
  • Aryl halide
  • Benzenoid
  • Azole
  • Oxazole
  • Heteroaromatic compound
  • Azacycle
  • Oxacycle
  • Organic oxide
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.96 g/LALOGPS
logP2.09ALOGPS
logP1.94ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.39ChemAxon
pKa (Strongest Basic)-2.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.07 m³·mol⁻¹ChemAxon
Polarizability14.94 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-02t9-7900000000-bf1beeca5227a276a1a9Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-02t9-7900000000-bf1beeca5227a276a1a9Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-014i-1900000000-77df83a0769511baeb96Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-60a947f3a3a65702c43bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-5049b81b3f21c5158973Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0900000000-c7ee77e191a097d4e0baNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lr-0900000000-004a71f655e522e841deNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-4900000000-b7b03cbc9d434e2b03f2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-003i-9100000000-8a0cf328f650c7cd4780Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-60a947f3a3a65702c43bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-b157f14bda84940ce6f0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-1160c69f5a00e22b993dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0900000000-4ad343b03b4421d4d5efNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0900000000-8f6b0f1e098737ec9a8bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0900000000-77cf5afa849168e0d47cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001l-2900000000-4530cefc3528a1ea69aaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0900000000-17303fd327c77e9416c7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014r-0900000000-ca9ae316c33b4d133176Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-1900000000-71762abc7b749630bea6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-b64f4a6255327486b59aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-57d2d934c4c43717f60cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ox-2900000000-e68db7b29f08e0ca69feNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
866.0Log mg/kg[490:1500]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
365Muscle relaxantsHealthcare, pharmaceuticals & veterinary productsNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
540X Ray TubesElectrical & Electronic EquipmentNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)1889.95
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)2156.97
SRSF protein kinase 1 structureClick to view 3D structureSRSF protein kinase 1Q96SB4HumansPredicted (SEA)878.139
Casein kinase I isoform gamma-1 structureClick to view 3D structureCasein kinase I isoform gamma-1Q9HCP0HumansPredicted (SEA)899.081
Cyclin-dependent kinase 5 structureClick to view 3D structureCyclin-dependent kinase 5Q00535HumansPredicted (SEA)1317.99
Mitogen-activated protein kinase kinase kinase kinase 4 structureClick to view 3D structureMitogen-activated protein kinase kinase kinase kinase 4O95819HumansPredicted (SEA)1401.6
STE20-like serine/threonine-protein kinase structureClick to view 3D structureSTE20-like serine/threonine-protein kinaseQ9H2G2HumansPredicted (SEA)1076.58
Lymphokine-activated killer T-cell-originated protein kinase structureClick to view 3D structureLymphokine-activated killer T-cell-originated protein kinaseQ96KB5HumansPredicted (SEA)820.142
Click to view 3D structureSerine/threonine-protein kinase TAO1Q7L7X3HumansPredicted (SEA)1247.61
Serine/threonine-protein kinase Chk1 structureClick to view 3D structureSerine/threonine-protein kinase Chk1O14757HumansPredicted (SEA)1520.78
Serine/threonine-protein kinase PLK4 structureClick to view 3D structureSerine/threonine-protein kinase PLK4O00444HumansPredicted (SEA)1237.26
Serine/threonine-protein kinase PLK3 structureClick to view 3D structureSerine/threonine-protein kinase PLK3Q9H4B4HumansPredicted (SEA)1179.49
Amine oxidase [flavin-containing] B structureClick to view 3D structureAmine oxidase [flavin-containing] BP27338HumansPredicted (SEA)594.612
LIM domain kinase 1 structureClick to view 3D structureLIM domain kinase 1P53667HumansPredicted (SEA)1251.43
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)654.011
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)822.788
Glycogen synthase kinase-3 alpha structureClick to view 3D structureGlycogen synthase kinase-3 alphaP49840HumansPredicted (SEA)1679.05
Cyclin-dependent kinase 1 structureClick to view 3D structureCyclin-dependent kinase 1P06493HumansPredicted (SEA)1507.32
Serine/threonine-protein kinase pim-1 structureClick to view 3D structureSerine/threonine-protein kinase pim-1P11309HumansPredicted (SEA)653.778
Dual specificity protein kinase CLK4 structureClick to view 3D structureDual specificity protein kinase CLK4Q9HAZ1HumansPredicted (SEA)612.284
Tyrosine-protein kinase JAK2 structureClick to view 3D structureTyrosine-protein kinase JAK2O60674HumansPredicted (SEA)1104.06
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)996.859
GTP-binding protein Rheb structureClick to view 3D structureGTP-binding protein RhebQ15382HumansPredicted (SEA)3.03612
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)858.443
Glycogen synthase kinase-3 beta structureClick to view 3D structureGlycogen synthase kinase-3 betaP49841HumansPredicted (SEA)1425.5
Concentrations
Not Available
External Links
DrugBank IDDB00356
HMDB IDHMDB0014500
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDCLW
Wikipedia LinkChlorzoxazone
Chemspider ID2632
ChEBI ID3655
PubChem Compound ID2733
Kegg Compound IDC07931
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Wan J, Ernstgard L, Song BJ, Shoaf SE: Chlorzoxazone metabolism is increased in fasted Sprague-Dawley rats. J Pharm Pharmacol. 2006 Jan;58(1):51-61.
2. Park JY, Kim KA, Park PW, Ha JM: Effect of high-dose aspirin on CYP2E1 activity in healthy subjects measured using chlorzoxazone as a probe. J Clin Pharmacol. 2006 Jan;46(1):109-14.
3. Dong DL, Luan Y, Feng TM, Fan CL, Yue P, Sun ZJ, Gu RM, Yang BF: Chlorzoxazone inhibits contraction of rat thoracic aorta. Eur J Pharmacol. 2006 Sep 18;545(2-3):161-6. Epub 2006 Jun 29.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=10640318
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=11727787
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=12437348
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=16763012
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=16859676
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=17621748
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21195386
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23975871
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24210069
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=25815637
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=6631711