General Information of Drug (ID: DR0312)
Drug Name
Chlorzoxazone
Synonyms
Chloroxazone; Chlorzoxane; Chlorzoxazon; Chlorzoxazonum; Escoflex; Mioran; Miotran; Myoflexin; Myoflexine; Neoflex; Biomioran; Paraflex; Parafon Forte DSC; Pathorysin; Solaxin; Strifon Forte Dsc; Usaf ma-10; chlorzoxazone; 2(3H)-Benzoxazolone, 5-chloro-; 2-Hydroxy-5-chlorobenzoxazole; 5-Chloro-2(3H)-benzoxazolone; 5-Chloro-2-benzoxazolinone; 5-Chloro-2-benzoxazolol; 5-Chloro-2-benzoxazolone; 5-Chloro-2-hydroxybenzoxazole; 5-Chlorobenzoxazol-2-one; 5-Chlorobenzoxazolidone; 5-Chlorobenzoxazolone; 95-25-0
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 169.56 Topological Polar Surface Area 38.3
Heavy Atom Count 11 Rotatable Bond Count 0
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
2733
PubChem SID
10133 ; 87091 ; 826390 ; 826422 ; 3139748 ; 6867174 ; 7767972 ; 7847836 ; 7886649 ; 8139927 ; 8149257 ; 8151769 ; 10321163 ; 10538622 ; 11110945 ; 11110946 ; 11336070 ; 11361309 ; 11363042 ; 11365604 ; 11368166 ; 11371339 ; 11373953 ; 11376328 ; 11462281 ; 11466191 ; 11467311 ; 11484813 ; 11485682 ; 11488965 ; 11490166 ; 11492102 ; 11493962 ; 16935856 ; 17404816 ; 24277702 ; 26611661 ; 26679366 ; 26747469 ; 26747470 ; 29221889 ; 46507755 ; 47291196 ; 47662345 ; 47736550 ; 47810813 ; 47959818 ; 48035200 ; 48334567 ; 48334568
ChEBI ID
CHEBI:3655
CAS Number
95-25-0
TTD Drug ID
D08ZEB
Formula
C7H4ClNO2
Canonical SMILES
C1=CC2=C(C=C1Cl)NC(=O)O2
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
6-hydroxychlorzoxazone DM001833
2734
Oxidation - 6-Hydroxylation 1 [6] , [7] , [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000651 Chlorzoxazone 6-hydroxychlorzoxazone Oxidation - 6-Hydroxylation CYP102A1 ... [6], [7], [8]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 102A1 (cyp102) DME1075 Bacillus megaterium
CPXB_BACMB
1.14.14.1
[2] , [3]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[4]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[4]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
⏷ Show the Full List of 6  DME(s)
References
1 Chlorzoxazone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Wild-type CYP102A1 as a biocatalyst: turnover of drugs usually metabolised by human liver enzymes. J Biol Inorg Chem. 2007 Mar;12(3):313-23.
3 The bacterial P450 BM3: a prototype for a biocatalyst with human P450 activities. Trends Biotechnol. 2007 Jul;25(7):289-98.
4 Prediction of human liver microsomal oxidations of 7-ethoxycoumarin and chlorzoxazone with kinetic parameters of recombinant cytochrome P-450 enzymes. Drug Metab Dispos. 1999 Nov;27(11):1274-80.
5 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
6 Robustness of chlorzoxazone as an in vivo measure of cytochrome P450 2E1 activity Br J Clin Pharmacol. 2004 Aug;58(2):190-200. doi: 10.1111/j.1365-2125.2004.02132.x.
7 Amalgamation of in-silico, in-vitro and in-vivo approach to establish glabridin as a potential CYP2E1 inhibitor. Xenobiotica. 2021 Jun;51(6):625-635. doi: 10.1080/00498254.2021.1883769.
8 Generation and Characterization of CYP2E1-Overexpressing HepG2 Cells to Study the Role of CYP2E1 in Hepatic Hypoxia-Reoxygenation Injury. Int J Mol Sci. 2023 May 1;24(9):8121. doi: 10.3390/ijms24098121.

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