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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:28:27 UTC
HMDB IDHMDB14410
Secondary Accession NumbersNone
Metabolite Identification
Common NameCrotamiton
DescriptionCrotamiton is only found in individuals that have used or taken this drug. It is a scabicidal and antipruritic agent available as a cream or lotion for topical use only. It is a colorless to slightly yellowish oil, having a faint amine-like odor. It is miscible with alcohol and with methanol.Crotamiton is an antiparasitic that is toxic to the scabies mite. Crotamiton also relieves itching by producing what is called a counter-irritation. As crotamiton evaporates from the skin, it produces a cooling effect. This cooling effect helps to divert your body's attention away from the itching.
Structure
Thumb
Synonyms
ValueSource
CrotalginChEBI
CrotamitoneChEBI
CrotamitonumChEBI
Crotonyl-N-ethyl-O-toluidineChEBI
N-Ethyl-O-crotonotoluidideChEBI
CrotaglinHMDB
Chemical FormulaC13H17NO
Average Molecular Weight203.2802
Monoisotopic Molecular Weight203.131014171
IUPAC NameN-ethyl-N-(2-methylphenyl)but-2-enamide
Traditional Nameeurax
CAS Registry Number483-63-6
SMILES
CCN(C(=O)C=CC)C1=CC=CC=C1C
InChI Identifier
InChI=1S/C13H17NO/c1-4-8-13(15)14(5-2)12-10-7-6-9-11(12)3/h4,6-10H,5H2,1-3H3/b8-4+
InChI KeyInChIKey=DNTGGZPQPQTDQF-XBXARRHUSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aminotoluenes. These are organic aromatic compounds containing a benzene that carries a single methyl group and one amino group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassToluenes
Direct ParentAminotoluenes
Alternative Parents
Substituents
  • Aminotoluene
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Carboxamide group
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antiparasitic Agents
  • Antipruritics
  • Pesticides
  • Scabicides
Application
  • Pharmaceutical
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.53e-01 g/LNot Available
LogP2.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.35 mg/mLALOGPS
logP2.7ALOGPS
logP3.09ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)-0.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.15 m3·mol-1ChemAxon
Polarizability23.07 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00265
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00265
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00265
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID599515
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCrotamiton
NuGOwiki LinkHMDB14410
Metagene LinkHMDB14410
METLIN IDNot Available
PubChem Compound688020
PDB IDNot Available
ChEBI ID774660
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Buffet M, Dupin N: Current treatments for scabies. Fundam Clin Pharmacol. 2003 Apr;17(2):217-25. [12667233 ]