chlorzoxazone 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |

Stem definitionDrug idCAS RN
626 95-25-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • chlorzoxazone
  • 5-Chlorobenzoxazolidone
  • chlorzoxazon
  • chloroxazone
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. (From Martindale, The Extra Pharmacopoea, 30th ed, p1202)
  • Molecular weight: 169.56
  • Formula: C7H4ClNO2
  • CLOGP: 1.87
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 38.33
  • ALOGS: -1.76
  • ROTB: 0
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
1.50 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.25 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 196.38 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 100 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 2.165 Moderate 0.78
caco2-efflux Caco-2 efflux ratio (BA/AB) 0.877 Moderate 0.78
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 92.470 10^-6 cm/s Moderate 0.78
dh-clint Dog hepatocyte intrinsic clearance 19.770 uL/min/10^6 cells Moderate 0.78
dppb Dog plasma protein binding (% unbound) 12.230 % Moderate 0.78
fcs-ppb Fetal calf serum protein binding (% unbound) 14.040 % Moderate 0.78
herg hERG pIC50 4.069 pIC50 Moderate 0.78
hh-clint Human hepatocyte intrinsic clearance 4.539 uL/min/10^6 cells Moderate 0.78
hlm-clint Human liver microsomal intrinsic clearance 60.674 uL/min/mg protein Moderate 0.78
hppb Human plasma protein binding (% unbound) 9.070 % Moderate 0.78
kinase-safety-class ACVR2A,ACVR2B,ALK,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,ERBB2,FLT3,GRK2,GSK3B,ITK,JAK1,JAK2,MAP3K1,MAP3K21,MAP3K7,MAPK7,MAPK9,MARK4,MTOR,NTRK2,PAK4,PDK1,PDK4,PDPK1,PIK3CB,PIK3CD,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,TEK,TTK,ULK1 44
kinase-selectivity-class ACVR2B,AXL,CDK9,DYRK1B,GRK2,MAPK7,TTK 7
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 0.818 Moderate 0.78
mh-clint Mouse hepatocyte intrinsic clearance 93.972 Moderate 0.78
mppb Mouse plasma protein binding (% unbound) 20.260 Moderate 0.78
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 0.256 Moderate 0.78
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 6.680 % Moderate 0.78
rh-clint Rat hepatocyte intrinsic clearance 9.099 uL/min/10^6 cells Moderate 0.78
rh-fuinc Rat hepatocyte fraction unbound in incubation 90.640 % Moderate 0.78
rppb Rat plasma protein binding (% unbound) 19.280 % Moderate 0.78
solubility-dd Solubility at pH 7.4 in DMSO 778.037 uM Moderate 0.78

Approvals:

DateAgencyCompanyOrphan
Aug. 15, 1958 FDA JANSSEN R AND D

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Intentional overdose 136.90 21.99 57 1869 93777 90532744
Intentional self-injury 110.97 21.99 36 1890 29298 90597223
Completed suicide 65.96 21.99 40 1886 145018 90481503
Toxicity to various agents 37.79 21.99 38 1888 287808 90338713
Pulmonary renal syndrome 37.36 21.99 7 1919 578 90625943
Stress cardiomyopathy 37.04 21.99 13 1913 13342 90613179
Depressed level of consciousness 30.28 21.99 19 1907 72765 90553756
Anti-neutrophil cytoplasmic antibody positive vasculitis 28.47 21.99 8 1918 3985 90622536
Stevens-Johnson syndrome 27.13 21.99 13 1913 29363 90597158
Loss of consciousness 27.09 21.99 23 1903 140215 90486306

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Secondary adrenocortical insufficiency 77.88 34.74 14 395 2085 42618841
Spinal column injury 49.38 34.74 8 401 639 42620287
Sensory disturbance 35.22 34.74 9 400 7014 42613912

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Intentional overdose 118.34 25.01 54 1906 132447 110454892
Intentional self-injury 89.08 25.01 31 1929 37398 110549941
Completed suicide 65.43 25.01 45 1915 242336 110345003
Secondary adrenocortical insufficiency 58.69 25.01 14 1946 4420 110582919
Stress cardiomyopathy 37.21 25.01 13 1947 15793 110571546
Pulmonary renal syndrome 36.09 25.01 7 1953 834 110586505
Spinal column injury 34.19 25.01 8 1952 2323 110585016
Toxicity to various agents 33.82 25.01 42 1918 480513 110106826
Dizziness 32.56 25.01 50 1910 698143 109889196
Loss of consciousness 31.95 25.01 27 1933 196279 110391060
Sensory disturbance 28.64 25.01 11 1949 17418 110569921
Anti-neutrophil cytoplasmic antibody positive vasculitis 27.49 25.01 8 1952 5409 110581930

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC M03BB03 MUSCULO-SKELETAL SYSTEM
MUSCLE RELAXANTS
MUSCLE RELAXANTS, CENTRALLY ACTING AGENTS
Oxazol, thiazine, and triazine derivatives
ATC M03BB53 MUSCULO-SKELETAL SYSTEM
MUSCLE RELAXANTS
MUSCLE RELAXANTS, CENTRALLY ACTING AGENTS
Oxazol, thiazine, and triazine derivatives
ATC M03BB73 MUSCULO-SKELETAL SYSTEM
MUSCLE RELAXANTS
MUSCLE RELAXANTS, CENTRALLY ACTING AGENTS
Oxazol, thiazine, and triazine derivatives
CHEBI has role CHEBI:35717 sedative
CHEBI has role CHEBI:51371 muscle relaxant
MeSH PA D009125 Muscle Relaxants, Central
MeSH PA D009465 Neuromuscular Agents
FDA PE N0000175730 Centrally-mediated Muscle Relaxation
FDA EPC N0000175737 Muscle Relaxant

Related Drugs by ATC class:

M03BB Oxazol, thiazine, and triazine derivatives 1 drug
chlormezanone

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Spasticity indication 221360009
Muscle Spasm with Pain indication
Alcoholism contraindication 7200002
Hepatic failure contraindication 59927004
Poisoning by acetaminophen contraindication 70273001
Liver function tests abnormal contraindication 166603001
Disease of liver contraindication 235856003 DOID:409
Drug-induced hepatitis contraindication 235876009




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.22 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Calcium-activated potassium channel subunit alpha-1 Ion channel OPENER EC50 4.52 SCIENTIFIC LITERATURE SCIENTIFIC LITERATURE
Nitric oxide synthase, inducible Enzyme IC50 4.85 CHEMBL
Nitric oxide synthase, brain Enzyme IC50 4.30 CHEMBL
Intermediate conductance calcium-activated potassium channel protein 4 Ion channel ACTIVATOR EC50 4 IUPHAR
Nitric oxide synthase, endothelial Enzyme IC50 5.06 CHEMBL
Nitric oxide synthase, brain Enzyme IC50 5.55 DRUG MATRIX
Small conductance calcium-activated potassium channel protein 2 Ion channel ACTIVATOR EC50 4.10 IUPHAR

External reference:

IDSource
4017882 VUID
N0000146235 NUI
D00771 KEGG_DRUG
2410 RXNORM
C0008296 UMLSCUI
CHEBI:3655 CHEBI
CLW PDB_CHEM_ID
CHEMBL1371 ChEMBL_ID
DB00356 DRUGBANK_ID
D002753 MESH_DESCRIPTOR_UI
2733 PUBCHEM_CID
748 INN_ID
2322 IUPHAR_LIGAND_ID
H0DE420U8G UNII
4369 MMSL
4433 MMSL
d00962 MMSL
001671 NDDF
400361007 SNOMEDCT_US
44908000 SNOMEDCT_US
4017882 VANDF
H0DE420U8G INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 0254-2005 TABLET 750 mg ORAL ANDA 11 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 0254-2053 TABLET 375 mg ORAL ANDA 11 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 0591-2520 TABLET 500 mg ORAL ANDA 12 sections
CHLORZOXAZONE Human Prescription Drug Label 1 16571-725 TABLET 375 mg ORAL ANDA 11 sections
CHLORZOXAZONE Human Prescription Drug Label 1 16571-726 TABLET 500 mg ORAL ANDA 11 sections
CHLORZOXAZONE Human Prescription Drug Label 1 16571-727 TABLET 750 mg ORAL ANDA 11 sections
CHLORZOXAZONE HUMAN PRESCRIPTION DRUG LABEL 1 16590-478 TABLET 500 mg ORAL ANDA 12 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 21695-569 TABLET 500 mg ORAL ANDA 12 sections
CHLORZOXAZONE HUMAN PRESCRIPTION DRUG LABEL 1 24470-923 TABLET 250 mg ORAL ANDA 12 sections
CHLORZOXAZONE HUMAN PRESCRIPTION DRUG LABEL 1 24470-940 TABLET 500 mg ORAL ANDA 13 sections
CHLORZOXAZONE HUMAN PRESCRIPTION DRUG LABEL 1 31722-974 TABLET 250 mg ORAL ANDA 10 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 33261-021 TABLET 500 mg ORAL ANDA 12 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 42254-076 TABLET 500 mg ORAL ANDA 12 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 42494-426 TABLET 500 mg ORAL ANDA 14 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 42494-427 TABLET 500 mg ORAL ANDA 14 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 45865-434 TABLET 500 mg ORAL ANDA 12 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 50090-0315 TABLET 500 mg ORAL ANDA 12 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 50090-0316 TABLET 500 mg ORAL ANDA 12 sections
CHLORZOXAZONE Human Prescription Drug Label 1 50090-7504 TABLET 500 mg ORAL ANDA 11 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 51862-338 TABLET 375 mg ORAL ANDA 14 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 51862-339 TABLET 500 mg ORAL ANDA 14 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 51862-340 TABLET 750 mg ORAL ANDA 14 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 53002-5760 TABLET 500 mg ORAL ANDA 12 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 54868-0735 TABLET 500 mg ORAL ANDA 12 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 55045-1594 TABLET 500 mg ORAL ANDA 12 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 55289-633 TABLET 500 mg ORAL ANDA 12 sections
Chlorzoxazone HUMAN PRESCRIPTION DRUG LABEL 1 55289-633 TABLET 500 mg ORAL ANDA 12 sections
CHLORZOXAZONE Human Prescription Drug Label 1 55700-951 TABLET 500 mg ORAL ANDA 12 sections
CHLORZOXAZONE Human Prescription Drug Label 1 59651-305 TABLET 375 mg ORAL ANDA 12 sections
CHLORZOXAZONE Human Prescription Drug Label 1 59651-306 TABLET 500 mg ORAL ANDA 12 sections