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

General Information of Drug (ID: DR1557)
Drug Name
Terbinafine hydrochloride
Synonyms
Terbinafina [Spanish]; Terbinafine (hydrochloride); Terbinafine HCl; Terbinafine hydrochioride; Terbinafine hydrochloride; Terbinafinum [Latin]; UNII-012C11ZU6G; (2E)-N,6,6-trimethyl-N-(1-naphthylmethyl)hept-2-en-4-yn-1-amine; (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine; (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalene methanamine; (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethylamine; 91161-71-6; BRN 4256376; CHEBI:9448; CHEMBL822; Corbinal; DOMXUEMWDBAQBQ-WEVVVXLNSA-N; G7RIW8S0XP; Lamasil; Lamisil; Lamisil Tablet; NCGC00159346-02; SF 86-327; SF-86-327; UNII-G7RIW8S0XP; terbinafine; (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine hydrochloride; (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethylamine hydrochloride; 012C11ZU6G; 78628-80-5; C21H26ClN; CHEBI:77614; CPD000469152; DRG-0286; Lamisil Krem; MFCD00145430; MycoVa; SF 86-327 hydrochloride
Indication Pityriasis versicolor [ICD11: 1F2D] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 327.9 Topological Polar Surface Area 3.2
Heavy Atom Count 23 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
5282481
ChEBI ID
CHEBI:77614
CAS Number
78628-80-5
TTD Drug ID
D01AYJ
Formula
C21H26ClN
Canonical SMILES
CC(C)(C)C#CC=CCN(C)CC1=CC=CC2=CC=CC=C21.Cl
InChI
1S/C21H25N.ClH/c1-21(2,3)15-8-5-9-16-22(4)17-19-13-10-12-18-11-6-7-14-20(18)19;/h5-7,9-14H,16-17H2,1-4H3;1H/b9-5+;
InChIKey
BWMISRWJRUSYEX-SZKNIZGXSA-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-Naphthaldehyde DM000508
6195
Oxidation - Deamination 1 [2]
Hydroxyterbinafine DM000502
21917706
Oxidation - Hydoxylation 1 [2]
N-Desmethylterbinafine DM000505
6443233
Oxidation - N-Demethylation 1 [2]
Terbinafine dihydrodiol derivative (1) DM000511 N. A. Oxidation - Dihydroxylation 1 [2]
Terbinafine dihydrodiol derivative (2) DM000512 N. A. Oxidation - Dihydroxylation 1 [2]
1-Naphthalenemethanol DM000509
20908
Reduction - Reduction 2 [2]
1-Naphthoic acid DM000510
6847
Oxidation - Oxidation 2 [2]
Carboxyterbinafine DM000504
6443234
Oxidation - Oxidation 2 [2]
N-Desmethylhydroxyterbinafine DM000503 N. A. Oxidation - Hydoxylation 2 [2]
N-Desmethylhydroxyterbinafine DM000503 N. A. Oxidation - N-Demethylation 2 [2] , [6]
N-Desmethylterbinafine dihydrodiol derivative (1) DM000507 N. A. Oxidation - N-Demethylation 2 [2]
N-Desmethylterbinafine dihydrodiol derivative (1) DM000507 N. A. Oxidation - Dihydroxylation 2 [2]
N-Desmethylterbinafine dihydrodiol derivative (2) DM000506 N. A. Oxidation - N-Demethylation 2 [2]
N-Desmethylterbinafine dihydrodiol derivative (2) DM000506 N. A. Oxidation - Dihydroxylation 2 [2]
⏷ Show the Full List of 14  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002408 Terbinafine hydrochloride Hydroxyterbinafine Oxidation - Hydoxylation CYP1A2 ... [2]
MR002409 Terbinafine hydrochloride N-Desmethylterbinafine Oxidation - N-Demethylation CYP3A4 ... [2]
MR002410 Terbinafine hydrochloride 1-Naphthaldehyde Oxidation - Deamination CYP3A4 ... [2]
MR002411 Terbinafine hydrochloride Terbinafine dihydrodiol derivative (1) Oxidation - Dihydroxylation CYP1A2 ... [2]
MR002412 Terbinafine hydrochloride Terbinafine dihydrodiol derivative (2) Oxidation - Dihydroxylation CYP1A2 ... [2]
MR002404 1-Naphthaldehyde 1-Naphthalenemethanol Reduction - Reduction Unclear [2]
MR002405 1-Naphthaldehyde 1-Naphthoic acid Oxidation - Oxidation Unclear [2]
MR002399 Hydroxyterbinafine N-Desmethylhydroxyterbinafine Oxidation - N-Demethylation CYP3A4 ... [2], [6]
MR002400 Hydroxyterbinafine Carboxyterbinafine Oxidation - Oxidation CYP1A2 ... [2]
MR002401 N-Desmethylterbinafine N-Desmethylhydroxyterbinafine Oxidation - Hydoxylation CYP1A2 ... [2]
MR002402 N-Desmethylterbinafine N-Desmethylterbinafine dihydrodiol derivative (2) Oxidation - Dihydroxylation CYP1A2 ... [2]
MR002403 N-Desmethylterbinafine N-Desmethylterbinafine dihydrodiol derivative (1) Oxidation - Dihydroxylation CYP1A2 ... [2]
MR002406 Terbinafine dihydrodiol derivative (1) N-Desmethylterbinafine dihydrodiol derivative (1) Oxidation - N-Demethylation CYP3A4 ... [2]
MR002407 Terbinafine dihydrodiol derivative (2) N-Desmethylterbinafine dihydrodiol derivative (2) Oxidation - N-Demethylation CYP3A4 ... [2]
⏷ Show the Full List of 14 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[4]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
Prostaglandin G/H synthase 1 (COX-1) DME0091 Homo sapiens
PGH1_HUMAN
1.14.99.1
[4]
Unclear metabolic mechanism (DME-unclear) DME1267 Anaerobutyricum hallii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1358 Anaerococcus hydrogenalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1361 Anaerotruncus colihominis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1362 Bacteroides caccae Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1363 Bacteroides cellulosilyticus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1364 Bacteroides coprophilus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1375 Bacteroides intestinalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1377 Bacteroides pectinophilus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1388 Bifidobacterium breve Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1400 Enterocloster bolteae Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1401 Clostridium scindens Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1403 Clostridium spiroforme Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1405 Clostridium symbiosum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1407 Collinsella intestinalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1408 Coprococcus comes Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1412 Dorea formicigenerans Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1413 Edwardsiella tarda Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1416 Enterobacter cancerogenus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1427 Eubacterium ventriosum Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1432 Hungatella hathewayi Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1446 Parabacteroides johnsonii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1449 Prevotella copri Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1451 Proteus penneri Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1454 Providencia stuartii Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1456 Roseburia intestinalis Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1458 Ruminococcus gnavus Not Available Not Available [5]
Unclear metabolic mechanism (DME-unclear) DME1459 Ruminococcus lactaris Not Available Not Available [5]
⏷ Show the Full List of 39  DME(s)
References
1 Rufinamide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Multiple cytochrome P-450s involved in the metabolism of terbinafine suggest a limited potential for drug-drug interactions. Drug Metab Dispos. 1999 Sep;27(9):1029-38.
3 Multiple cytochrome P-450s involved in the metabolism of terbinafine suggest a limited potential for drug-drug interactions Drug Metab Dispos. 1999 Sep;27(9):1029-38.
4 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
5 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
6 A multi-residue chiral liquid chromatography coupled with tandem mass spectrometry method for analysis of antifungal agents and their metabolites in aqueous environmental matrices. Anal Methods. 2021 Jun 14;13(22):2466-2477. doi: 10.1039/d1ay00556a.

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