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

General Information of Drug (ID: DR1005)
Drug Name
Mebendazole
Synonyms
Mebendazol; Mebendazolum; Mebendazolum [INN-Latin]; Mebenoazole; Mebenvet; Mebutar; Noverme; Ovitelmin; Pantelmin; Telmin; Bantenol; Besantin; Equivurm Plus; Lomper; Vermicidin; Vermirax; Vermox; Verpanyl; Versid; mebendazole; 31431-39-7; 5-Benzoyl-2-benzimidazolecarbamic acid methyl ester; Carbamic acid, (5-benzoyl-1H-benzimidazol-2-yl)-, methyl ester; MBDZ; Mebex; Methyl (5-benzoyl-1H-benzo[d]imidazol-2-yl)carbamate; Methyl 5-benzoyl-2-benzimidazolecarbamate; Methyl 5-benzoyl-2-benzimidazolylcarbamate; Sufil
Indication Ascariasis [ICD11: 1F62] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 295.29 Topological Polar Surface Area 84.1
Heavy Atom Count 22 Rotatable Bond Count 4
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
4030
PubChem SID
447580 ; 603018 ; 841968 ; 855610 ; 934559 ; 3206369 ; 3314033 ; 4782129 ; 7659513 ; 7847434 ; 7979874 ; 8149709 ; 8152521 ; 10321384 ; 10589234 ; 11109644 ; 11112718 ; 11139496 ; 11335926 ; 11361165 ; 11364192 ; 11366754 ; 11369316 ; 11372497 ; 11373851 ; 11377478 ; 11462137 ; 11466245 ; 11467365 ; 11485178 ; 11485890 ; 11489217 ; 11491254 ; 11492231 ; 11495112 ; 11500651 ; 14898153 ; 24870130 ; 24896742 ; 26612167 ; 26675660 ; 26680066 ; 26746927 ; 26746928 ; 29223141 ; 46508807 ; 47291163 ; 47365215 ; 47365216 ; 47589024
ChEBI ID
ChEBI:6704
CAS Number
31431-39-7
TTD Drug ID
D0J1MI
Formula
C16H13N3O3
Canonical SMILES
COC(=O)NC1=NC2=C(N1)C=C(C=C2)C(=O)C3=CC=CC=C3
InChI
1S/C16H13N3O3/c1-22-16(21)19-15-17-12-8-7-11(9-13(12)18-15)14(20)10-5-3-2-4-6-10/h2-9H,1H3,(H2,17,18,19,21)
InChIKey
OPXLLQIJSORQAM-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
2-amino-5-benzoylbenzimidazole DM006470
40320
Oxidation - Decarboxylation 1 [2]
Methyl-5-(alpha-5-hydroxybenzyl)-2-benzimidazole carbamate DM006471 N. A. Unclear 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006951 Mebendazole 2-amino-5-benzoylbenzimidazole Oxidation - Decarboxylation CYP3A4 [2]
MR006952 Mebendazole Methyl-5-(alpha-5-hydroxybenzyl)-2-benzimidazole carbamate Unclear Unclear [4]
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) DME1251 Bacteroides fragilis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1363 Bacteroides cellulosilyticus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1366 Bacteroides eggerthii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1377 Bacteroides pectinophilus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1379 Bacteroides stercoris Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1391 Bifidobacterium ruminatum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1445 Parabacteroides distasonis Not Available Not Available [3]
⏷ Show the Full List of 16  DME(s)
References
1 Mebendazole was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Alveolar echinococcosis of the liver in an adult with human immunodeficiency virus type-1 infection. Infection. 2004 Oct;32(5):299-302.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Hardman, J.G., L.E. Limbird, P.B., A.G. Gilman. Goodman and Gilman's The Pharmacological Basis of Therapeutics. 10th ed. New York, NY: McGraw-Hill, 2001., p. 1126

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