ContaminantDB: Niclosamide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (47)XML

Record Information

Version

1.0

Creation Date

2013-04-25 07:56:53 UTC

Update Date

2026-05-14 18:25:21 UTC

Accession Number

CHEM002852

Identification

Common Name

Niclosamide

Class

Small Molecule

Description

Niclosamide is used for the treatment of most tapeworm infections. Helminths (worms) are multicellular organisms that infect very large numbers of humans and cause a broad range of diseases. Over 1 billion people are infected with intestinal nematodes, and many millions are infected with filarial nematodes, flukes, and tapeworms. They are an even greater problem in domestic animals.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Drug
Ester
Metabolite
Organic Compound
Organochloride
Pesticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Niclocide	Kegg
Aventis brand OF niclosamide	HMDB
Bayer brand OF niclosamide	HMDB
Fenasal	HMDB
Bayer 73	HMDB
Bayluscide	HMDB
Clonitralide	HMDB
Yomesan	HMDB
Bayer 2353	HMDB
Niclosamide, 2-aminoethanol (1:1)	HMDB
Phenasal	HMDB
Radewerm	HMDB
Trédémine	HMDB

Chemical Formula

C₁₃H₈Cl₂N₂O₄

Average Molecular Mass

327.120 g/mol

Monoisotopic Mass

325.986 g/mol

CAS Registry Number

50-65-7

IUPAC Name

5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide

Traditional Name

niclosamide

SMILES

OC1=C(C=C(Cl)C=C1)C(=O)NC1=C(Cl)C=C(C=C1)[N+]([O-])=O

InChI Identifier

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)

InChI Key

RJMUSRYZPJIFPJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Anilides

Direct Parent

Benzanilides

Alternative Parents

Substituents

Benzanilide
Salicylamide
Salicylic acid or derivatives
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Benzamide
Benzoic acid or derivatives
Nitrobenzene
Nitroaromatic compound
Benzoyl
4-halophenol
4-chlorophenol
1-hydroxy-2-unsubstituted benzenoid
Chlorobenzene
Halobenzene
Phenol
Aryl chloride
Aryl halide
Vinylogous acid
Secondary carboxylic acid amide
Organic nitro compound
Carboxamide group
C-nitro compound
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Carboxylic acid derivative
Organic oxoazanium
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Organohalogen compound
Organochloride
Organonitrogen compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic zwitterion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	230°C
Boiling Point	Not Available
Solubility	1.6 mg/L (at 20°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.008 g/L	ALOGPS
logP	4.49	ALOGPS
logP	3.91	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	6.89	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.51 m³·mol⁻¹	ChemAxon
Polarizability	28.47 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-6901000000-2b365b023e021b160f32	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-8930000000-69bd67a318e9efd73dde	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0006-2920000000-abe97627fbae89daa0db	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-0029000000-07d09d3c05d206cf1709	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00dr-0982000000-be44b0c8755c752ba0f3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-0910000000-4aa0326731fc70d171de	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-0900000000-d166a8246615e944705a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-0900000000-8da8fb85b28f330b445d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-0abi-0900000000-10c251c2f1c5006a7f25	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0fka-5952000000-25e2c37ca8eb59d1db22	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9200000000-57c28b8b2b3dc926256d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9100000000-2b567071c6cfa78ecf55	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9100000000-33d3827b1d5b1d8b0dd1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9000000000-9cee7be3f0ec47a2cf6e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0002-9000000000-cf3d1288bd0150e477be	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-004i-0519000000-8dd141b868e2002a2bfa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0udi-4900000000-d83bc5ee9b78c460078c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-00di-0900000000-1c2167607d05b47594fb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-00di-0900000000-25ef559cdcba657ec7bf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-00di-0910000000-137a6a40379842639b2a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-00dr-0982000000-c63ef31f0e3de2dbbbd1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0009000000-19d348ccf2b61b75bf34	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0009000000-7d6ea94b8683b59260b8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-0639000000-2cc47cc1fb3e56e9be10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0009000000-720f5eedf2a446e4de88	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0009000000-9146e1b30ee98c36f42b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05bf-6629000000-77e8ecb80b64e657ec0f	Spectrum

Toxicity Profile

Route of Exposure

Niclosamide appears to be minimally absorbed from the gastrointestinal tract - neither the drug nor its metabolites have been recovered from the blood or urine.

Mechanism of Toxicity

Niclosamide works by killing tapeworms on contact. Adult worms (but not ova) are rapidly killed, presumably due to uncoupling of oxidative phosphorylation or stimulation of ATPase activity. The killed worms are then passed in the stool or sometimes destroyed in the intestine. Niclosamide may work as a molluscicide by binding to and damaging DNA.

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment of tapeworm and intestinal fluke infections: Taenia saginata (Beef Tapeworm), Taenia solium (Pork Tapeworm), Diphyllobothrium latum (Fish Tapeworm), Fasciolopsis buski (large intestinal fluke). Niclosamide is also used as a molluscicide in the control of schistosomiasis.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID