Details of the Drug

General Information of Drug (ID: DMCYVDT)

Drug Name
Chlorzoxazone
Synonyms
Biomioran; CLW; Chloroxazone; Chlorsoxazone; Chlorzoxane; Chlorzoxazon; Chlorzoxazona; Chlorzoxazonum; Clorzoxazona; Escoflex; Klorzoxazon; Mioran; Miotran; Myoflexin; Myoflexine; Neoflex; Nyoflex; Paraflex; Parafon; Pathorysin; Relaxazone; Remofleks; Remular; Solaxin; Component of Parafon Forte; McNeil Brand of Chlorzoxazone; Ortho Brand of Chlorzoxazone; Parafon Forte; Parafon Forte DSC; Strifon Forte Dsc; C 4397; Chlorzoxazonum [INN-Latin]; Clorzoxazona [INN-Spanish]; EZE-DS; Muscol (TN); Paraflex (TN); Parafon Forte (TN); Remular-S; Usaf ma-10; Chlorzoxazone [INN:BAN:JAN]; Chlorzoxazone (JAN/USP/INN); 2-Hydroxy-5-chlorobenzoxazole; 5-Chlorbenzoxazolin-2-on; 5-Chloro-1,3-benzoxazol-2(3H)-one; 5-Chloro-2(3H)-benzoxazolone; 5-Chloro-2-benzoxazolinone; 5-Chloro-2-benzoxazolol; 5-Chloro-2-benzoxazolone; 5-Chloro-2-hydroxybenzoxazole; 5-Chloro-3(H)-2-benzoxazolone; 5-Chlorobenzoksazolinon-2; 5-Chlorobenzoksazolinon-2 [Polish]; 5-Chlorobenzoksazolon-2; 5-Chlorobenzoksazolon-2 [Polish]; 5-Chlorobenzoxazol-2-one; 5-Chlorobenzoxazolidone; 5-Chlorobenzoxazolone; 5-chloro-1,3-benzoxazol-2-ol; 5-chloro-3H-1,3-benzoxazol-2-one; 5-chlorobenzoxazolin-2-one
Indication
Disease Entry ICD 11 Status REF
Acute pain MG31 Approved [1]
Therapeutic Class
Analgesics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 169.56
Logarithm of the Partition Coefficient (xlogp) 1.8
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
Elimination
0.5% of drug is excreted from urine in the unchanged form [2]
Metabolism
The drug is metabolized via the liver []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 196.38089 micromolar/kg/day [3]
Water Solubility
The ability of drug to dissolve in water is measured as 0.25 mg/mL [2]
Chemical Identifiers
Formula
C7H4ClNO2
IUPAC Name
5-chloro-3H-1,3-benzoxazol-2-one
Canonical SMILES
C1=CC2=C(C=C1Cl)NC(=O)O2
InChI
InChI=1S/C7H4ClNO2/c8-4-1-2-6-5(3-4)9-7(10)11-6/h1-3H,(H,9,10)
InChIKey
TZFWDZFKRBELIQ-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
2733
ChEBI ID
CHEBI:3655
CAS Number
95-25-0
DrugBank ID
DB00356
TTD ID
D08ZEB
VARIDT ID
DR00571
INTEDE ID
DR0312
ACDINA ID
D00127
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Calcium-activated potassium channel (KCN) TTMNI76 NOUNIPROTAC Activator [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [5]
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Substrate [6]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [7]
Cytochrome P450 2A6 (CYP2A6) DEJVYAZ CP2A6_HUMAN Substrate [7]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [8]
Cytochrome P450 102A1 (cyp102) DE4OGUF CPXB_BACMB Substrate [9], [10]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Arylamine N-acetyltransferase 2 (NAT2) OTBPDQOY ARY2_HUMAN Regulation of Drug Effects [11]
Cytochrome P450 1B1 (CYP1B1) OTYXFLSD CP1B1_HUMAN Gene/Protein Processing [12]
Intermediate conductance calcium-activated potassium channel protein 4 (KCNN4) OTQKQ346 KCNN4_HUMAN Gene/Protein Processing [13]
Xanthine dehydrogenase/oxidase OTT40HOD XDH_HUMAN Regulation of Drug Effects [11]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Chlorzoxazone
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Oliceridine DM6MDCF Major Additive CNS depression effects by the combination of Chlorzoxazone and Oliceridine. Acute pain [MG31] [14]
Coadministration of a Drug Treating the Disease Different from Chlorzoxazone (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Remdesivir DMBFZ6L Moderate Increased risk of hepatotoxicity by the combination of Chlorzoxazone and Remdesivir. 1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019] [15]
Bedaquiline DM3906J Moderate Increased risk of hepatotoxicity by the combination of Chlorzoxazone and Bedaquiline. Antimicrobial drug resistance [MG50-MG52] [16]
Pexidartinib DMS2J0Z Major Increased risk of hepatotoxicity by the combination of Chlorzoxazone and Pexidartinib. Bone/articular cartilage neoplasm [2F7B] [17]
Dihydrocodeine DMB0FWL Major Additive CNS depression effects by the combination of Chlorzoxazone and Dihydrocodeine. Chronic pain [MG30] [18]
Olopatadine DMKMWQG Moderate Additive CNS depression effects by the combination of Chlorzoxazone and Olopatadine. Conjunctiva disorder [9A60] [19]
Alfentanil DMVO0UB Major Additive CNS depression effects by the combination of Chlorzoxazone and Alfentanil. Corneal disease [9A76-9A78] [14]
Remifentanil DMZTXCH Major Additive CNS depression effects by the combination of Chlorzoxazone and Remifentanil. Corneal disease [9A76-9A78] [14]
Ethanol DMDRQZU Moderate Additive CNS depression effects by the combination of Chlorzoxazone and Ethanol. Cystitis [GC00] [19]
Esketamine DMVU687 Moderate Additive CNS depression effects by the combination of Chlorzoxazone and Esketamine. Depression [6A70-6A7Z] [15]
Cannabidiol DM0659E Moderate Increased risk of hepatotoxicity by the combination of Chlorzoxazone and Cannabidiol. Epileptic encephalopathy [8A62] [20]
Brimonidine DMQLT4N Moderate Additive CNS depression effects by the combination of Chlorzoxazone and Brimonidine. Glaucoma [9C61] [21]
Isoniazid DM5JVS3 Moderate Decreased metabolism of Chlorzoxazone caused by Isoniazid mediated inhibition of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [22]
Brentuximab vedotin DMWLC57 Moderate Increased risk of hepatotoxicity by the combination of Chlorzoxazone and Brentuximab vedotin. Hodgkin lymphoma [2B30] [23]
Efavirenz DMC0GSJ Moderate Increased risk of hepatotoxicity by the combination of Chlorzoxazone and Efavirenz. Human immunodeficiency virus disease [1C60-1C62] [24]
Abacavir DMMN36E Minor Increased plasma concentrations of Chlorzoxazone and Abacavir due to competitive inhibition of the same metabolic pathway. Human immunodeficiency virus disease [1C60-1C62] [25]
Mipomersen DMGSRN1 Major Increased risk of hepatotoxicity by the combination of Chlorzoxazone and Mipomersen. Hyper-lipoproteinaemia [5C80] [26]
Teriflunomide DMQ2FKJ Major Increased risk of hepatotoxicity by the combination of Chlorzoxazone and Teriflunomide. Hyper-lipoproteinaemia [5C80] [27]
Methotrexate DM2TEOL Moderate Increased risk of hepatotoxicity by the combination of Chlorzoxazone and Methotrexate. Leukaemia [2A60-2B33] [20]
Ceritinib DMB920Z Moderate Decreased metabolism of Chlorzoxazone caused by Ceritinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [15]
Calaspargase pegol DMQZBXI Moderate Increased risk of hepatotoxicity by the combination of Chlorzoxazone and Calaspargase pegol. Malignant haematopoietic neoplasm [2B33] [28]
Idelalisib DM602WT Moderate Increased risk of hepatotoxicity by the combination of Chlorzoxazone and Idelalisib. Mature B-cell leukaemia [2A82] [29]
Clofarabine DMCVJ86 Moderate Increased risk of hepatotoxicity by the combination of Chlorzoxazone and Clofarabine. Mature B-cell lymphoma [2A85] [30]
Allopregnanolone DMNLHAC Moderate Additive CNS depression effects by the combination of Chlorzoxazone and Allopregnanolone. Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z] [31]
Lasmiditan DMXLVDT Moderate Additive CNS depression effects by the combination of Chlorzoxazone and Lasmiditan. Migraine [8A80] [32]
Flibanserin DM70DTN Moderate Additive CNS depression effects by the combination of Chlorzoxazone and Flibanserin. Mood disorder [6A60-6E23] [33]
Levomethadyl Acetate DM06HG5 Major Additive CNS depression effects by the combination of Chlorzoxazone and Levomethadyl Acetate. Opioid use disorder [6C43] [18]
Apraclonidine DMO4PVE Moderate Additive CNS depression effects by the combination of Chlorzoxazone and Apraclonidine. Optic nerve disorder [9C40] [21]
Pentazocine DM1XBHS Major Additive CNS depression effects by the combination of Chlorzoxazone and Pentazocine. Pain [MG30-MG3Z] [14]
Butorphanol DM5KYPJ Major Additive CNS depression effects by the combination of Chlorzoxazone and Butorphanol. Pain [MG30-MG3Z] [14]
Oxymorphone DM65AGJ Major Additive CNS depression effects by the combination of Chlorzoxazone and Oxymorphone. Pain [MG30-MG3Z] [14]
Levorphanol DMGS80V Major Additive CNS depression effects by the combination of Chlorzoxazone and Levorphanol. Pain [MG30-MG3Z] [14]
Dezocine DMJDB0Y Major Additive CNS depression effects by the combination of Chlorzoxazone and Dezocine. Pain [MG30-MG3Z] [14]
Nalbuphine DMOSQGU Major Additive CNS depression effects by the combination of Chlorzoxazone and Nalbuphine. Pain [MG30-MG3Z] [14]
Buprenorphine DMPRI8G Major Additive CNS depression effects by the combination of Chlorzoxazone and Buprenorphine. Pain [MG30-MG3Z] [34]
Hydrocodone DMQ2JO5 Major Additive CNS depression effects by the combination of Chlorzoxazone and Hydrocodone. Pain [MG30-MG3Z] [14]
Meperidine DMX4GND Major Additive CNS depression effects by the combination of Chlorzoxazone and Meperidine. Pain [MG30-MG3Z] [14]
Oxycodone DMXLKHV Major Additive CNS depression effects by the combination of Chlorzoxazone and Oxycodone. Pain [MG30-MG3Z] [14]
Leflunomide DMR8ONJ Major Increased risk of hepatotoxicity by the combination of Chlorzoxazone and Leflunomide. Rheumatoid arthritis [FA20] [27]
Fentanyl DM8WAHT Major Additive CNS depression effects by the combination of Chlorzoxazone and Fentanyl. Sensation disturbance [MB40] [14]
Sufentanil DMU7YEL Major Additive CNS depression effects by the combination of Chlorzoxazone and Sufentanil. Sensation disturbance [MB40] [14]
Trabectedin DMG3Y89 Moderate Increased risk of hepatotoxicity by the combination of Chlorzoxazone and Trabectedin. Solid tumour/cancer [2A00-2F9Z] [20]
Disulfiram DMCL2OK Moderate Decreased metabolism of Chlorzoxazone caused by Disulfiram mediated inhibition of CYP450 enzyme. Substance abuse [6C40] [35]
Naltrexone DMUL45H Moderate Increased risk of hepatotoxicity by the combination of Chlorzoxazone and Naltrexone. Substance abuse [6C40] [36]
Tizanidine DMR2IQ4 Moderate Additive CNS depression effects by the combination of Chlorzoxazone and Tizanidine. Tonus and reflex abnormality [MB47] [37]
⏷ Show the Full List of 44 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Docusate sodium E00563 23673837 Surfactant
FD&C blue no. 1 E00263 19700 Colorant
Quinoline yellow WS E00309 24671 Colorant
Sodium benzoate E00432 517055 Antimicrobial preservative; lubricant
Beta-D-lactose E00099 6134 Diluent; Dry powder inhaler carrier; Lyophilization aid
Carmellose sodium E00625 Not Available Disintegrant
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate E00208 11177 lubricant
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
⏷ Show the Full List of 9 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Chlorzoxazone 500 mg tablet 500 mg Oral Tablet Oral
Chlorzoxazone 250 mg tablet 250 mg Oral Tablet Oral
Chlorzoxazone 375 mg tablet 375 mg Oral Tablet Oral
Chlorzoxazone 750 mg tablet 750 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

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2 BDDCS applied to over 900 drugs
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6 Trimethadione metabolism by human liver cytochrome P450: evidence for the involvement of CYP2E1. Xenobiotica. 1998 Nov;28(11):1041-7.
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11 Effects of cigarette smoking and carbon monoxide on chlorzoxazone and caffeine metabolism. Clin Pharmacol Ther. 2003 Nov;74(5):468-74. doi: 10.1016/j.clpt.2003.07.001.
12 Association of CYP1A1 and CYP1B1 inhibition in in vitro assays with drug-induced liver injury. J Toxicol Sci. 2021;46(4):167-176. doi: 10.2131/jts.46.167.
13 Functional and molecular identification of intermediate-conductance Ca(2+)-activated K(+) channels in breast cancer cells: association with cell cycle progression. Am J Physiol Cell Physiol. 2004 Jul;287(1):C125-34. doi: 10.1152/ajpcell.00488.2003. Epub 2004 Feb 25.
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18 US Food and Drug Administration "FDA warns about serious risks and death when combining opioid pain or cough medicines with benzodiazepines requires its strongest warning.".
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23 Product Information. Adcetris (brentuximab vedotin). Seattle Genetics Inc, Bothell, WA.
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25 Product Information. Ziagen (abacavir). Glaxo Wellcome, Research Triangle Pk, NC.
26 Product Information. Kynamro (mipomersen). Genzyme Corporation, Cambridge, MA.
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30 Product Information. Clolar (clofarabine). sanofi-aventis, Bridgewater, NJ.
31 Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
32 Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
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37 Product Information. Zanaflex (tizanidine). Acorda Therapeutics, Hawthorne, NY.