Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:04 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. They are an even greater problem in domestic animals. Niclosamide is a drug which is used 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. Niclosamide is an extremely weak basic (essentially neutral) compound (based on its pKa). Niclosamide works by killing tapeworms on contact. Niclosamide is a potentially toxic compound. Helminths (worms) are multicellular organisms that infect very large numbers of humans and cause a broad range of diseases. Adult worms (but not ova) are rapidly killed, presumably due to uncoupling of oxidative phosphorylation or stimulation of ATPase activity. Over 1 billion people are infected with intestinal nematodes, and many millions are infected with filarial nematodes, flukes, and tapeworms.
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

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+167.33630932474
DeepCCS[M-H]-164.97830932474
DeepCCS[M-2H]-198.57830932474
DeepCCS[M+Na]+174.74330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NiclosamideOC1=C(C=C(Cl)C=C1)C(=O)NC1=C(Cl)C=C(C=C1)[N+]([O-])=O4312.3Standard polar33892256
NiclosamideOC1=C(C=C(Cl)C=C1)C(=O)NC1=C(Cl)C=C(C=C1)[N+]([O-])=O2761.0Standard non polar33892256
NiclosamideOC1=C(C=C(Cl)C=C1)C(=O)NC1=C(Cl)C=C(C=C1)[N+]([O-])=O2820.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Niclosamide,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(Cl)C=C1C(=O)NC1=CC=C([N+](=O)[O-])C=C1Cl2892.3Semi standard non polar33892256
Niclosamide,1TMS,isomer #2C[Si](C)(C)N(C(=O)C1=CC(Cl)=CC=C1O)C1=CC=C([N+](=O)[O-])C=C1Cl2622.7Semi standard non polar33892256
Niclosamide,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(Cl)C=C1C(=O)N(C1=CC=C([N+](=O)[O-])C=C1Cl)[Si](C)(C)C2615.5Semi standard non polar33892256
Niclosamide,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(Cl)C=C1C(=O)N(C1=CC=C([N+](=O)[O-])C=C1Cl)[Si](C)(C)C2683.0Standard non polar33892256
Niclosamide,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(Cl)C=C1C(=O)N(C1=CC=C([N+](=O)[O-])C=C1Cl)[Si](C)(C)C3175.4Standard polar33892256
Niclosamide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(Cl)C=C1C(=O)NC1=CC=C([N+](=O)[O-])C=C1Cl3149.5Semi standard non polar33892256
Niclosamide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)C1=CC(Cl)=CC=C1O)C1=CC=C([N+](=O)[O-])C=C1Cl2886.7Semi standard non polar33892256
Niclosamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(Cl)C=C1C(=O)N(C1=CC=C([N+](=O)[O-])C=C1Cl)[Si](C)(C)C(C)(C)C3157.2Semi standard non polar33892256
Niclosamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(Cl)C=C1C(=O)N(C1=CC=C([N+](=O)[O-])C=C1Cl)[Si](C)(C)C(C)(C)C3128.2Standard non polar33892256
Niclosamide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(Cl)C=C1C(=O)N(C1=CC=C([N+](=O)[O-])C=C1Cl)[Si](C)(C)C(C)(C)C3315.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Niclosamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-6901000000-2b365b023e021b160f322017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Niclosamide GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-8930000000-69bd67a318e9efd73dde2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Niclosamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide LC-ESI-qTof , Positive-QTOFsplash10-0006-2920000000-abe97627fbae89daa0db2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , negative-QTOFsplash10-00di-0029000000-07d09d3c05d206cf17092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , negative-QTOFsplash10-00dr-0982000000-be44b0c8755c752ba0f32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , negative-QTOFsplash10-00di-0910000000-4aa0326731fc70d171de2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , negative-QTOFsplash10-00di-0900000000-d166a8246615e944705a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , negative-QTOFsplash10-00di-0900000000-8da8fb85b28f330b445d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , negative-QTOFsplash10-0abi-0900000000-10c251c2f1c5006a7f252017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , positive-QTOFsplash10-0fka-5952000000-25e2c37ca8eb59d1db222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , positive-QTOFsplash10-0002-9200000000-57c28b8b2b3dc926256d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , positive-QTOFsplash10-0002-9100000000-2b567071c6cfa78ecf552017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , positive-QTOFsplash10-0002-9100000000-33d3827b1d5b1d8b0dd12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , positive-QTOFsplash10-0002-9000000000-9cee7be3f0ec47a2cf6e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide LC-ESI-QFT , positive-QTOFsplash10-0002-9000000000-cf3d1288bd0150e477be2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide , positive-QTOFsplash10-004i-0519000000-8dd141b868e2002a2bfa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide , positive-QTOFsplash10-0udi-4900000000-d83bc5ee9b78c460078c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide 60V, Negative-QTOFsplash10-00di-0900000000-1c2167607d05b47594fb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide 75V, Negative-QTOFsplash10-00di-0900000000-25ef559cdcba657ec7bf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide 45V, Negative-QTOFsplash10-00di-0910000000-137a6a40379842639b2a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Niclosamide 30V, Negative-QTOFsplash10-00dr-0982000000-c63ef31f0e3de2dbbbd12021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niclosamide 10V, Positive-QTOFsplash10-004i-0009000000-19d348ccf2b61b75bf342016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niclosamide 20V, Positive-QTOFsplash10-004i-0009000000-7d6ea94b8683b59260b82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niclosamide 40V, Positive-QTOFsplash10-056r-0639000000-2cc47cc1fb3e56e9be102016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niclosamide 10V, Negative-QTOFsplash10-00di-0009000000-720f5eedf2a446e4de882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niclosamide 20V, Negative-QTOFsplash10-00di-0009000000-9146e1b30ee98c36f42b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Niclosamide 40V, Negative-QTOFsplash10-05bf-6629000000-77e8ecb80b64e657ec0f2016-08-03Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB06803 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
MarkerDB IDNot Available
Good Scents 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 ]