Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0803)
Drug Name
Halothane
Synonyms
Halotan; Halotano; Halotano [INN-Spanish]; Halothan; Halothanum; Halothanum [INN-Latin]; Halsan; Narcotan; Narcotane; Narkotan; Alotano; Alotano [DCIT]; Anestan; Bromchlortrifluoraethanum; Bromochlorotrifluoroethane; Chalothane; Fluktan; Fluorotane; Fluothane; Freon 123B1; Ftorotan; Ftorotan [Russian]; Ftuorotan; Phthorothanum; Rhodialothan; halothane; 1,1,1-Trifluoro-2-chloro-2-bromoethane; 1-Bromo-1-chloro-2,2,2-trifluoroethane; 151-67-7; 2,2,2-Trifluoro-1-chloro-1-bromoethane; 2-BROMO-2-CHLORO-1,1,1-TRIFLUOROETHANE; Halan
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 197.38 Topological Polar Surface Area 0
Heavy Atom Count 7 Rotatable Bond Count 0
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
3562
PubChem SID
9718 ; 428040 ; 3159200 ; 5123763 ; 7847608 ; 7979527 ; 8145848 ; 8152252 ; 10508848 ; 15067445 ; 17388981 ; 24850204 ; 24891772 ; 29222693 ; 46506589 ; 48423484 ; 48425179 ; 49855046 ; 53790292 ; 56311498 ; 56311785 ; 56311842 ; 56311861 ; 56313444 ; 56313445 ; 56313447 ; 57321872 ; 76126220 ; 92308210 ; 103242558 ; 104006665 ; 104303878 ; 114917783 ; 124890113 ; 124890114 ; 125539176 ; 126677461 ; 127269303 ; 127269304 ; 127269305 ; 127269306 ; 127269307 ; 127269308 ; 127269309 ; 127269310 ; 127269311 ; 127269312 ; 127269313 ; 127269314 ; 127269315
ChEBI ID
ChEBI:5615
CAS Number
151-67-7
TTD Drug ID
D0D8VE
Formula
C2HBrClF3
Canonical SMILES
C(C(F)(F)F)(Cl)Br
InChI
1S/C2HBrClF3/c3-1(4)2(5,6)7/h1H
InChIKey
BCQZXOMGPXTTIC-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
1-chloro-2,2,2-trifluoroethanide DM004732 N. A. Reduction - Dehalogenation 1 [5] , [8]
2-chloro-1,1-difluoroethene DM004731
9664
Reduction - Dehalogenation 1 [8]
2-chloro-1,1-difluoroethene DM004731
9664
Reduction - Dehalogenation 1 [5] , [8]
Bromide DM004730
259
Oxidation - Oxidationn 1 [9]
Chlorotrifluoroethane DM004734
6408
Reduction - Dehalogenation 1 [8]
Trifluoroacetic acid DM001003
6422
Oxidation - Oxidationn 1 [9]
Trifluoroacetyl chloride DM004733
61106
Reduction - Dehalogenation 1 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005081 Halothane Bromide Oxidation - Oxidationn CYP2E1 [9]
MR005082 Halothane Trifluoroacetic acid Oxidation - Oxidationn CYP2E1 [9]
MR005083 Halothane 2-chloro-1,1-difluoroethene Reduction - Dehalogenation CYP2A6 ... [5], [8]
MR005084 Halothane 1-chloro-2,2,2-trifluoroethanide Reduction - Dehalogenation CYP2A6 ... [5], [8]
MR005085 Halothane Trifluoroacetyl chloride Reduction - Dehalogenation CYP2E1 ... [8]
MR005086 Halothane Chlorotrifluoroethane Reduction - Dehalogenation CYP3A4 ... [8]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[5]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[6]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Microsomal cytochrome MCB5 (CYB5A) DME0411 Homo sapiens
CYB5_HUMAN
1.14.14.1
[7]
⏷ Show the Full List of 7  DME(s)
References
1 Halothane was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Halothane-dependent lipid peroxidation in human liver microsomes is catalyzed by cytochrome P4502A6 (CYP2A6). Anesthesiology. 2001 Aug;95(2):509-14.
3 Bupropion and 4-OH-bupropion pharmacokinetics in relation to genetic polymorphisms in CYP2B6. Pharmacogenetics. 2003 Oct;13(10):619-26.
4 Human reductive halothane metabolism in vitro is catalyzed by cytochrome P450 2A6 and 3A4. Drug Metab Dispos. 1996 Sep;24(9):976-83.
5 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
6 Concordance between trifluoroacetic acid and hepatic protein trifluoroacetylation after disulfiram inhibition of halothane metabolism in rats. Acta Anaesthesiol Scand. 2003 Jul;47(6):765-70.
7 Modulation of the reductive metabolism of halothane by microsomal cytochrome b5 in rat liver. Biochim Biophys Acta. 1987 Dec 7;926(3):231-8.
8 Cytochromes P450: a structure-based summary of biotransformations using representative substrates Drug Metab Rev. 2008;40(1):1-100. doi: 10.1080/03602530802309742.
9 DrugBank(Pharmacology-Metabolism):Halothane

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