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]
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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)

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

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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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]

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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.