Details of the Drug

General Information of Drug (ID: DMJAGXQ)

Drug Name

Niclosamide

Synonyms

niclosamide; 50-65-7; Niclocide; 5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide; Tredemine; Bayluscid; Phenasal; Yomesan; Fenasal; Dichlosale; Helmiantin; Sagimid; Iomezan; Devermine; Atenase; Vermitid; Radeverm; Mansonil; Iomesan; Devermin; Cestocid; Sulqui; Lintex; Nasemo; Mato; Fedal-Telmin; Bayer 73; Radewerm; Zestocarp; Bayer 2353; 2',5-Dichloro-4'-nitrosalicylanilide; Chemagro 2353; BAY 2353; Benzamide, 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxy-; 5-Chloro-2'-chloro-4'-nitrosalicylanilide; nicolsamide; HL 2447; Niclosamidum [I

Indication

Disease Entry	ICD 11	Status	REF
Cestodes infection	1F70-1F76	Approved	[1], [2]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

327.12

Topological Polar Surface Area (xlogp)

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [3]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 87.34 micromolar/kg/day [4]
Water Solubility: The ability of drug to dissolve in water is measured as 0.013 mg/mL [3]

Chemical Identifiers

Formula: C13H8Cl2N2O4
IUPAC Name: 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide
Canonical SMILES: C1=CC(=C(C=C1[N+](=O)[O-])Cl)NC(=O)C2=C(C=CC(=C2)Cl)O
InChI: 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

Cross-matching ID

PubChem CID: 4477
ChEBI ID: CHEBI:7553
CAS Number: 50-65-7
DrugBank ID: DB06803
TTD ID: D0J9ZR
INTEDE ID: DR1146

Molecular Interaction Atlas of This Drug

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2C9 (CYP2C9)	DE5IED8	CP2C9_HUMAN	Substrate	[5]
Nitroreductase (NTR)	DE0K82S	A0A5K1UB29_SALTM	Substrate	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 8494).
2	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3	BDDCS applied to over 900 drugs
4	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5	Generation and evaluation of a CYP2C9 heteroactivation pharmacophore. J Pharmacol Exp Ther. 2003 Dec;307(3):878-87.
6	CYP1A1 and Cnr nitroreductase bioactivated niclosamide in vitro. Mutagenesis. 2013 Nov;28(6):645-51.
7	Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9.
8	Tamoxifen inhibits cytochrome P450 2C9 activity in breast cancer patients. J Chemother. 2006 Aug;18(4):421-4.
9	Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98.
10	Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.
11	Drug-drug interactions with imatinib: an observational study. Medicine (Baltimore). 2016 Oct;95(40):e5076.
12	Drug interactions with calcium channel blockers: possible involvement of metabolite-intermediate complexation with CYP3A. Drug Metab Dispos. 2000 Feb;28(2):125-30.
13	New insights into the structural features and functional relevance of human cytochrome P450 2C9. Part I. Curr Drug Metab. 2009 Dec;10(10):1075-126.
14	A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7.
15	A mechanistic approach to antiepileptic drug interactions. Ann Pharmacother. 1998 May;32(5):554-63.
16	Purification and characterization of wild-type and mutant "classical" nitroreductases of Salmonella typhimurium. L33R mutation greatly diminishes binding of FMN to the nitroreductase of S. typhimurium. J Biol Chem. 1998 Sep 11;273(37):23922-8.
17	Prenatal diagnosis of junctional epidermolysis bullosa Herlitz type. Lancet. 1989 Oct 28;2(8670):1035-6. Letter