Human Metabolome Database Version 3.5

Showing metabocard for Niclosamide (HMDB15679)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:52 -0600
Update Date 2013-02-08 17:34:15 -0700
HMDB ID HMDB15679
Secondary Accession Numbers None
Metabolite Identification
Common Name Niclosamide
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.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Chemical Formula C13H8Cl2N2O4
Average Molecular Weight 327.12
Monoisotopic Molecular Weight 325.986112168
IUPAC Name 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide
Traditional IUPAC Name niclosamide
CAS Registry Number 50-65-7
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 Key RJMUSRYZPJIFPJ-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Anilides
Sub Class N/A
Other Descriptors
  • Aromatic Homopolycyclic Compounds
  • Benzamides
  • Nitrobenzenes
  • Organic Compounds
Substituents
  • Aryl Chloride
  • Benzoyl
  • Carboxamide Group
  • Chlorobenzene
  • Nitro Compound
  • Organic Oxoazanium
  • Organochloride
  • Phenol
  • Phenol Derivative
  • Secondary Carboxylic Acid Amide
Direct Parent Anilides
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Anthelmintics
  • Antiparasitic Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.008 g/L ALOGPS
LogP 4.49 ALOGPS
LogP 3.91 ChemAxon
LogS -4.61 ALOGPS
pKa (strongest acidic) 6.89 ChemAxon
pKa (strongest basic) -4.4 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 95.15 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 80.51 ChemAxon
Polarizability 28.47 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB06803
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB06803
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB06803 Link_out
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 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Niclosamide Link_out
NuGOwiki Link HMDB15679 Link_out
Metagene Link HMDB15679 Link_out
METLIN ID Not Available
PubChem Compound 4477 Link_out
PDB ID Not Available
ChEBI ID 478218 Link_out
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_out

Enzymes
Name: Cytochrome P450 2C9
Reactions: Not Available
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions: Not Available
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA