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

General Information of Drug (ID: DR1016)
Drug Name
Mefloquine hydrochloride
Synonyms
Mefloquin; Mefloquina; Mefloquina [INN-Spanish]; Mefloquine [USAN:INN:BAN]; Mefloquinum; Mefloquinum [INN-Latin]; Mephloquine; Loriam; Mefloquin Hydrochloride; Mefloquine (hydrochloride); Mefloquine HCL; Mefloquine hydrochloride; Mephaquin; Ro 21-5998/001; WR 142490 hydrochloride; (AS)-rel-a-(2R)-2-Piperidinyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol monohydrochloride; 326VC85GV6; 51773-92-3; DL-erythro-alpha-2-Piperidyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol monohydrochloride; DSSTox_CID_27796; DSSTox_GSID_47819; DSSTox_RID_82568; EINECS 257-412-0; MLS001332559; NSC 157387; UNII-326VC85GV6; RTI1189-1-1; Racemic mefloquine; Ro 21-5998; Ro 215998; WR 142490; mefloquine; (-)-(11S,2'R)-erythro-Mefloquine; (-)-Mefloquine; (DL-erythro-alpha-2-Piperidyl-2,8-bis(trifluoromethyl)-4-quinolinemethanol; (S)-[2,8-bis(trifluoromethyl)quinolin-4-yl][(2R)-piperidin-2-yl]methanol; 53230-10-7; CHEBI:63687; CHEMBL172; HSDB 6853
Indication Malaria [ICD11: 1F40] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 414.8 Topological Polar Surface Area 45.2
Heavy Atom Count 27 Rotatable Bond Count 2
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
65329
ChEBI ID
CHEBI:6719
CAS Number
51742-86-0
TTD Drug ID
D0GQ7K
Formula
C17H17ClF6N2O
Canonical SMILES
C1CCNC(C1)C(C2=CC(=NC3=C2C=CC=C3C(F)(F)F)C(F)(F)F)O.Cl
InChI
1S/C17H16F6N2O.ClH/c18-16(19,20)11-5-3-4-9-10(15(26)12-6-1-2-7-24-12)8-13(17(21,22)23)25-14(9)11;/h3-5,8,12,15,24,26H,1-2,6-7H2;1H/t12-,15+;/m1./s1
InChIKey
WESWYMRNZNDGBX-YLCXCWDSSA-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
2,8-Bis(trifluoromethyl)quinoline-4-carboxylic acid DM001093
169721
Oxidation - N-Demethylation 1 [4]
Alcohol DM001094 N. A. Unclear 1 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001632 Mefloquine hydrochloride 2,8-Bis(trifluoromethyl)quinoline-4-carboxylic acid Oxidation - N-Demethylation CYP3A4 [4]
MR001633 Mefloquine hydrochloride Alcohol Unclear Unclear [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1415 Eggerthella lenta Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1452 Providencia alcalifaciens Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1456 Roseburia intestinalis Not Available Not Available [3]
References
1 Mefloquine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effect of rifampin on plasma concentrations of mefloquine in healthy volunteers. J Pharm Pharmacol. 2000 Oct;52(10):1265-9.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Synthetic and natural compounds that interact with human cytochrome P450 1A2 and implications in drug development. Curr Med Chem. 2009;16(31):4066-218.

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