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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:42:02 UTC
HMDB IDHMDB0015679
Secondary Accession Numbers
  • HMDB15679
Metabolite Identification
Common NameNiclosamide
DescriptionNiclosamide, also known as niclocide or fenasal, 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. Niclosamide's metabolic effects are relevant to wide ranges of organisms, and accordingly it has been applied as a control measure to organisms other than tapeworms. Side effects include nausea, vomiting, abdominal pain, constipation, and itchiness. Niclosamide, sold under the trade name Niclocide among others, is a medication used to treat tapeworm infestations. The wholesale cost in the developing world is about 0.24 USD for a course of treatment. Niclosamide is a drug. Niclosamide is an extremely weak basic (essentially neutral) compound (based on its pKa). Niclosamide is a potentially toxic compound. For some of these reasons, praziquantel is a preferable and equally effective treatment for tapeworm infestation.
Structure
Data?1582753322
Synonyms
ValueSource
NiclocideKegg
Aventis brand OF niclosamideHMDB
Bayer brand OF niclosamideHMDB
FenasalHMDB
Bayer 73HMDB
BayluscideHMDB
ClonitralideHMDB
YomesanHMDB
Bayer 2353HMDB
Niclosamide, 2-aminoethanol (1:1)HMDB
PhenasalHMDB
RadewermHMDB
TrédémineHMDB
Chemical FormulaC13H8Cl2N2O4
Average Molecular Weight327.12
Monoisotopic Molecular Weight325.986112168
IUPAC Name5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide
Traditional Nameniclosamide
CAS Registry Number50-65-7
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 KeyRJMUSRYZPJIFPJ-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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentBenzanilides
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 FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.008 g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-6901000000-2b365b023e021b160f32Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-8930000000-69bd67a318e9efd73ddeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0006-2920000000-abe97627fbae89daa0dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-0029000000-07d09d3c05d206cf1709Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00dr-0982000000-be44b0c8755c752ba0f3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-0910000000-4aa0326731fc70d171deSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-0900000000-d166a8246615e944705aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-0900000000-8da8fb85b28f330b445dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0abi-0900000000-10c251c2f1c5006a7f25Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0fka-5952000000-25e2c37ca8eb59d1db22Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9200000000-57c28b8b2b3dc926256dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9100000000-2b567071c6cfa78ecf55Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9100000000-33d3827b1d5b1d8b0dd1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9000000000-9cee7be3f0ec47a2cf6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-9000000000-cf3d1288bd0150e477beSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-004i-0519000000-8dd141b868e2002a2bfaSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-4900000000-d83bc5ee9b78c460078cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-19d348ccf2b61b75bf34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0009000000-7d6ea94b8683b59260b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-0639000000-2cc47cc1fb3e56e9be10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-720f5eedf2a446e4de88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0009000000-9146e1b30ee98c36f42bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05bf-6629000000-77e8ecb80b64e657ec0fSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06803 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06803 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06803
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4322
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNiclosamide
METLIN IDNot Available
PubChem Compound4477
PDB IDNot Available
ChEBI ID478218
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot 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 ]