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

General Information of Drug (ID: DR1146)
Drug Name
Niclosamide
Synonyms
Nasemo; Niclocide; Phenasal; Radeverm; Radewerm; Sagimid; Sulqui; Tredemine; Vermitid; Yomesan; Zestocarp; niclosamide; nicolsamide; Atenase; Bayluscid; Cestocid; Devermin; Devermine; Dichlosale; Fedal-Telmin; Fenasal; Helmiantin; Iomesan; Iomezan; Lintex; Mansonil; 2',5-Dichloro-4'-nitrosalicylanilide; 5-Chloro-2'-chloro-4'-nitrosalicylanilide; 5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide; 50-65-7; BAY 2353; Bayer 2353; Bayer 73; Benzamide, 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxy-; Chemagro 2353; HL 2447; Mato
Indication Tapeworm infestation [ICD11: 1F7Y] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 327.12 Topological Polar Surface Area 95.2
Heavy Atom Count 21 Rotatable Bond Count 2
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
4477
PubChem SID
446537 ; 635963 ; 5010826 ; 5010827 ; 7847502 ; 7980120 ; 8149966 ; 8152760 ; 10321405 ; 10852038 ; 11111533 ; 11111534 ; 11335884 ; 11361123 ; 11363133 ; 11365695 ; 11368257 ; 11371653 ; 11373910 ; 11376419 ; 11462095 ; 11466068 ; 11467188 ; 11484961 ; 11485796 ; 11488999 ; 11490483 ; 11492011 ; 11494053 ; 12159141 ; 14924163 ; 17405839 ; 24278585 ; 24862257 ; 26612455 ; 26680237 ; 26747596 ; 26753613 ; 29223572 ; 46511793 ; 47242136 ; 47365202 ; 47662299 ; 47810766 ; 47885430 ; 47959760 ; 48035132 ; 48035133 ; 48259243 ; 48334504
ChEBI ID
CHEBI:7553
CAS Number
50-65-7
TTD Drug ID
D0J9ZR
Formula
C13H8Cl2N2O4
Canonical SMILES
C1=CC(=C(C=C1[N+](=O)[O-])Cl)NC(=O)C2=C(C=CC(=C2)Cl)O
InChI
1S/C13H8Cl2N2O4/c14-7-1-4-12(18)9(5-7)13(19)16-11-3-2-8(17(20)21)6-10(11)15/h1-6,18H,(H,16,19)
InChIKey
RJMUSRYZPJIFPJ-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
3-hydroxy niclosamide DM002176 N. A. Oxidation - Hydroxylation 1 [4]
Niclosamide-2-O-glucuronide metabolite DM002177 N. A. Conjugation - Glucuronidation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001734 Niclosamide 3-hydroxy niclosamide Oxidation - Hydroxylation CYP1A2 [4]
MR001735 Niclosamide Niclosamide-2-O-glucuronide metabolite Conjugation - Glucuronidation UGT1A1 ... [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Nitroreductase (NTR) DME1968 Salmonella typhimurium
A0A5K1UB29_SALTM
1.5.1.39
[3]
References
1 Niclosamide was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Generation and evaluation of a CYP2C9 heteroactivation pharmacophore. J Pharmacol Exp Ther. 2003 Dec;307(3):878-87.
3 CYP1A1 and Cnr nitroreductase bioactivated niclosamide in vitro. Mutagenesis. 2013 Nov;28(6):645-51.
4 Metabolism of the anthelmintic drug niclosamide by cytochrome P450 enzymes and UDP-glucuronosyltransferases: metabolite elucidation and main contributions from CYP1A2 and UGT1A1 Xenobiotica. 2016;46(1):1-13. doi: 10.3109/00498254.2015.1047812.

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