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

General Information of Drug (ID: DR0199)
Drug Name
CAM-2028
Synonyms
BENZYDAMINE; Bencidamina; Bencidamina [INN-Spanish]; Benzidamina [DCIT]; Benzidamine; Benzindamine; Benzydamine [INN:BAN]; Benzydaminum; Benzydaminum [INN-Latin]; CNBGNNVCVSKAQZ-UHFFFAOYSA-N; 1-Benzyl-3-(3-(dimethylamino)propoxy)-1H-indazole; 1-Benzyl-3-[3-(dimethylamino)propoxy]-1H-indazole; 1-Propanamine, N,N-dimethyl-3-((1-(phenylmethyl)-1H-indazol-3-yl)oxy)-; 1H-Indazole, 1-benzyl-3-(3-(dimethylamino)propoxy)-; 4O21U048EF; 642-72-8; BRN 0896536; C 1523; C19H23N3O; EINECS 211-388-8; UNII-4O21U048EF
Indication Acute nasopharyngitis [ICD11: CA00] Discontinued [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 309.4 Topological Polar Surface Area 30.3
Heavy Atom Count 23 Rotatable Bond Count 7
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
12555
PubChem SID
3249272 ; 7363241 ; 8159401 ; 10531547 ; 11112291 ; 11466325 ; 11467445 ; 11486189 ; 14874196 ; 29280766 ; 47275667 ; 47573479 ; 47720705 ; 48394035 ; 49698422 ; 49834400 ; 49982452 ; 50100409 ; 51091839 ; 57327692 ; 76715658 ; 77054122 ; 85788423 ; 88727191 ; 92309318 ; 92714382 ; 93625695 ; 103172857 ; 103993136 ; 104329316 ; 117474939 ; 117522969 ; 117843309 ; 125324610 ; 126624183 ; 126674680 ; 127649080 ; 131813289 ; 134976246 ; 137001338 ; 142768192 ; 144054864 ; 160657813 ; 162186786 ; 166244320 ; 176484560 ; 179149820 ; 184644018 ; 198937676 ; 223365688
ChEBI ID
ChEBI:40538
CAS Number
642-72-8
TTD Drug ID
D06FJO
Formula
C19H23N3O
Canonical SMILES
CN(C)CCCOC1=NN(C2=CC=CC=C21)CC3=CC=CC=C3
InChI
1S/C19H23N3O/c1-21(2)13-8-14-23-19-17-11-6-7-12-18(17)22(20-19)15-16-9-4-3-5-10-16/h3-7,9-12H,8,13-15H2,1-2H3
InChIKey
CNBGNNVCVSKAQZ-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
Dealkylated metabolite DM005550
75181
Unclear 1 [7]
EBenzydamine N-oxid DM005548
65465
Unclear 1 [5] , [6]
Hydroxy metabolite DM005551
125299062
Unclear 1 [7]
N-oxide hydroxy metabolite DM005552 N. A. Unclear 1 [7]
Norbenzydamine DM005549
57369683
Unclear 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005915 CAM-2028 EBenzydamine N-oxid Unclear FMO1 ... [5], [6]
MR005916 CAM-2028 Norbenzydamine Unclear CYP2D6 [5]
MR005917 CAM-2028 Dealkylated metabolite Unclear Unclear [7]
MR005918 CAM-2028 Hydroxy metabolite Unclear Unclear [7]
MR005919 CAM-2028 N-oxide hydroxy metabolite Unclear Unclear [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[3]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
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
[2]
Dimethylaniline oxidase 1 (FMO1) DME0059 Homo sapiens
FMO1_HUMAN
1.14.13.8
[5] , [6]
Dimethylaniline oxidase 3 (FMO3) DME0039 Homo sapiens
FMO3_HUMAN
1.14.13.8
[5] , [6]
Dimethylaniline oxidase 4 (FMO4) DME0637 Homo sapiens
FMO4_HUMAN
1.14.13.8
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[4]
⏷ Show the Full List of 9  DME(s)
References
1 Emerging drugs for chemotherapy-induced mucositis. Expert Opin Emerg Drugs. 2008 Sep;13(3):511-22.
2 In vitro evaluation of potential in vivo probes for human flavin-containing monooxygenase (FMO): metabolism of benzydamine and caffeine by FMO and P450 isoforms. Br J Clin Pharmacol. 2000 Oct;50(4):311-4.
3 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
4 Characterization of moclobemide N-oxidation in human liver microsomes. Xenobiotica. 2001 Jul;31(7):387-97.
5 Benzydamine N-oxygenation as an index for flavin-containing monooxygenase activity and benzydamine N-demethylation by cytochrome P450 enzymes in liver microsomes from rats, dogs, monkeys, and humans
6 Human plasma metabolic profiles of benzydamine, a flavin-containing monooxygenase probe substrate, simulated with pharmacokinetic data from control and humanized-liver mice
7 Pharmacology of benzydamine

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