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]
Haemophilus influenza 1G40 Approved [2]
Taeniasis N.A. Approved [2]
Affected Organisms
Helminthic Microorganisms
ATC Code
P02DA01: Niclosamide
P02DA: Salicylic acid derivatives
P02D: ANTICESTODALS
P02: ANTHELMINTICS
P: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 327.12
Logarithm of the Partition Coefficient (xlogp) 4
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 4
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
CHEMBL1448
CAS Number
50-65-7
UNII
8KK8CQ2K8G
DrugBank ID
DB06803
TTD ID
D0J9ZR
INTEDE ID
DR1146
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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]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
17-beta-hydroxysteroid dehydrogenase 14 (HSD17B14) OT0ETO72 DHB14_HUMAN Gene/Protein Processing [7]
2'-5'-oligoadenylate synthase 1 (OAS1) OT8ZLOCY OAS1_HUMAN Gene/Protein Processing [7]
2,4-dienoyl-CoA reductase , mitochondrial (DECR1) OTCDIR6X DECR_HUMAN Gene/Protein Processing [8]
24-hydroxycholesterol 7-alpha-hydroxylase (CYP39A1) OTBAJT4I CP39A_HUMAN Gene/Protein Processing [9]
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1 (HSD3B1) OTNAZVKB 3BHS1_HUMAN Gene/Protein Processing [7]
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2 (HSD3B2) OT02MSKN 3BHS2_HUMAN Gene/Protein Processing [7]
3',5'-cyclic-AMP phosphodiesterase 4B (PDE4B) OTOA8WU2 PDE4B_HUMAN Gene/Protein Processing [7]
3'-5' exoribonuclease HELZ2 (HELZ2) OTM6HVO6 HELZ2_HUMAN Gene/Protein Processing [7]
4-hydroxy-2-oxoglutarate aldolase, mitochondrial (HOGA1) OT7XETW4 HOGA1_HUMAN Gene/Protein Processing [7]
5'(3')-deoxyribonucleotidase, mitochondrial (NT5M) OTJF73BA NT5M_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) 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 Niclosamide FDA Label
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 Mitochondrial Uncoupling Induces Epigenome Remodeling and Promotes Differentiation in Neuroblastoma. Cancer Res. 2023 Jan 18;83(2):181-194. doi: 10.1158/0008-5472.CAN-22-1029.
8 Growth inhibition of ovarian tumor-initiating cells by niclosamide. Mol Cancer Ther. 2012 Aug;11(8):1703-12.
9 Computational discovery of niclosamide ethanolamine, a repurposed drug candidate that reduces growth of hepatocellular carcinoma cells initro and in mice by inhibiting cell division cycle 37 signaling. Gastroenterology. 2017 Jun;152(8):2022-2036.