Niclosamide

Common Name

Niclosamide Description

Niclosamide is used for the treatment of most tapeworm infections. Helminths (worms) are mliticellliar 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. Structure

Synonyms

Value Source NiclocideKegg Aventis brand OF niclosamideMeSH Bayer brand OF niclosamideMeSH FenasalMeSH Bayer 73MeSH BayluscideMeSH ClonitralideMeSH YomesanMeSH Bayer 2353MeSH Niclosamide, 2-aminoethanol (1:1)MeSH PhenasalMeSH RadewermMeSH TrédémineMeSH

Chemical Formlia

C₁₃H₈Cl₂N₂O₄ Average Molecliar Weight

327.12 Monoisotopic Molecliar Weight

325.986112168 IUPAC Name

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

niclosamide CAS Registry Number

50-65-7 SMILES

InChI Identifier

InChI Key

RJMUSRYZPJIFPJ-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities 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

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Benzanilides Alternative Parents

Salicylamides

3-halobenzoic acids and derivatives

Benzamides

Nitrobenzenes

P-chlorophenols

Benzoyl derivatives

Nitroaromatic compounds

1-hydroxy-2-unsubstituted benzenoids

Chlorobenzenes

Aryl chlorides

Vinylogous acids

Secondary carboxylic acid amides

Propargyl-type 1,3-dipolar organic compounds

Organic oxoazanium compounds

Hydrocarbon derivatives

Organic zwitterions

Organochlorides

Organonitrogen compounds

Organooxygen compounds

Organopnictogen compounds

Organic oxides

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

Molecliar Framework

Aromatic homomonocyclic compounds External Descriptors

Not Available Ontology Status

Expected but not Quantified Origin

Drug

Biofunction

Anthelmintics

Antiparasitic Agents

Application

Pharmaceutical

Cellliar locations

Cytoplasm

Membrane

Physical Properties State

Solid Experimental Properties

Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

Predicted Properties

Property Value Source Water Solubility0.008 mg/mLALOGPS logP4.49ALOGPS logP3.91ChemAxon logS-4.6ALOGPS pKa (Strongest Acidic)6.89ChemAxon pKa (Strongest Basic)-4.4ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count4ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area95.15 ŲChemAxon Rotatable Bond Count3ChemAxon Refractivity80.51 m³·mol^-1ChemAxon Polarizability28.47 ųChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

Spectra Spectra

Spectrum Type Description Splash Key LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-00di-0029000000-07d09d3c05d206cf1709View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-00dr-0982000000-be44b0c8755c752ba0f3View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-00di-0910000000-4aa0326731fc70d171deView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-00di-0900000000-d166a8246615e944705aView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-00di-0900000000-8da8fb85b28f330b445dView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , negativesplash10-0abi-0900000000-10c251c2f1c5006a7f25View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0fka-5952000000-25e2c37ca8eb59d1db22View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0002-9200000000-57c28b8b2b3dc926256dView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0002-9100000000-2b567071c6cfa78ecf55View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0002-9100000000-33d3827b1d5b1d8b0dd1View in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0002-9000000000-9cee7be3f0ec47a2cf6eView in MoNA LC-MS/MS

LC-MS/MS Spectrum – LC-ESI-QFT , positivesplash10-0002-9000000000-cf3d1288bd0150e477beView in MoNA LC-MS/MS

LC-MS/MS Spectrum – , positivesplash10-004i-0519000000-8dd141b868e2002a2bfaView in MoNA LC-MS/MS

LC-MS/MS Spectrum – , positivesplash10-0udi-4900000000-d83bc5ee9b78c460078cView in MoNA Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

Biological Properties Cellliar Locations

Cytoplasm

Membrane

Biofluid Locations

Blood

Urine

Tissue Location

Not Available Pathways

Not Available Normal Concentrations

Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06803

21059682

details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06803

21059682

details

Abnormal Concentrations

Not Available Predicted Concentrations

Biofluid Value Original age Original sex Original condition Comments Blood0-3 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-2 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

Associated Disorders and Diseases Disease References

None Associated OMIM IDs

None External Links DrugBank ID

DB06803 DrugBank Metabolite ID

Not Available Phenol Explorer Compound ID

Not Available Phenol Explorer Metabolite ID

Not Available FoodDB ID

Not Available KNApSAcK ID

Not Available Chemspider ID

4322 KEGG Compound ID

Not Available BioCyc ID

Not Available BiGG ID

Not Available Wikipedia Link

Niclosamide NuGOwiki Link

HMDB15679 Metagene Link

HMDB15679 METLIN ID

Not Available PubChem Compound

4477 PDB ID

Not Available ChEBI ID

478218

Product: TCS JNK 6a

References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References

1. (). 2010. Detailed Drug Information for the Consumerâ„¢. Greenwood Village, CO. Thomson Reuters. ISBN-10: 1-56363-575-5. ISSN: 0740-4174. STAT!Ref Online Electronic Medical Library.. .
2. Clinical Pharmacology of the Antihelminthic Drugs Chapter 53). Katzung BG: Basic & Clinical Pharmacology, 12th edition [Link]

Enzymes

General function:

Involved in monooxygenase activity

Specific function:

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.

Gene Name:

CYP2C9

Uniprot ID:

P11712

Molecular weight:

55627.365

References

1. Bapiro TE, Egnell AC, Hasler JA, Masimirembwa CM: Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Drug Metab Dispos. 2001 Jan;29(1):30-5. [PubMed:11124226 ]

General function:

Involved in monooxygenase activity

Specific function:

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.

Gene Name:

CYP1A2

Uniprot ID:

P05177

Molecular weight:

58406.915

References

1. Bapiro TE, Egnell AC, Hasler JA, Masimirembwa CM: Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Drug Metab Dispos. 2001 Jan;29(1):30-5. [PubMed:11124226 ]

PMID: 12408704

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