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Identification
NameCrotamiton
Accession NumberDB00265  (APRD00211)
TypeSmall Molecule
GroupsApproved
Description

Crotamiton 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.

Structure
Thumb
Synonyms
SynonymLanguageCode
EuraxNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Euraxcream100 mg/gtopicalRanbaxy Laboratories Inc.2008-12-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Euraxlotion100 mg/gtopicalRanbaxy Laboratories Inc.2008-11-13Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
CrotamitexGepepharm
EuracinGreen Cross (South Korea)
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number483-63-6
WeightAverage: 203.2802
Monoisotopic: 203.131014171
Chemical FormulaC13H17NO
InChI KeyDNTGGZPQPQTDQF-XBXARRHUSA-N
InChI
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+
IUPAC Name
N-ethyl-N-(2-methylphenyl)but-2-enamide
SMILES
CCN(C(=O)C=CC)C1=CC=CC=C1C
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
Pharmacology
IndicationFor eradication of scabies (Sarcoptes scabiei) and for symptomatic treatment of pruritic skin.
PharmacodynamicsCrotamiton is usually used to treat pruritis (itching of the skin) caused by scabies or sunburn. Crotamiton 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. Due to this cooling effect it is also effective for the relief of sunburn. The drug is also believed to kill scabies through an unknown mechanism.
Mechanism of actionCrotamiton 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.
Absorption10 % absorbed when applied locally.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9905
Blood Brain Barrier+0.9939
Caco-2 permeable+0.8303
P-glycoprotein substrateNon-substrate0.788
P-glycoprotein inhibitor INon-inhibitor0.8611
P-glycoprotein inhibitor IINon-inhibitor0.709
Renal organic cation transporterNon-inhibitor0.8494
CYP450 2C9 substrateNon-substrate0.7767
CYP450 2D6 substrateNon-substrate0.6383
CYP450 3A4 substrateSubstrate0.586
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 substrateNon-inhibitor0.9071
CYP450 2D6 substrateNon-inhibitor0.9461
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-inhibitor0.831
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7792
Ames testNon AMES toxic0.7386
CarcinogenicityCarcinogens 0.5946
BiodegradationNot ready biodegradable0.9764
Rat acute toxicity2.1007 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9726
hERG inhibition (predictor II)Non-inhibitor0.8168
Pharmacoeconomics
Manufacturers
  • Ranbaxy laboratories inc
  • Summers laboratories inc
Packagers
Dosage forms
FormRouteStrength
Creamtopical100 mg/g
Lotiontopical100 mg/g
Prices
Unit descriptionCostUnit
Eurax 10% Lotion 454 gm Bottle353.03USD bottle
Eurax 10% Lotion 60 gm Bottle54.21USD bottle
Eurax 10% Cream 60 gm Tube51.99USD tube
Eurax 10% cream0.27USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateLiquid
Experimental Properties
PropertyValueSource
melting point< 25 °CPhysProp
boiling point154 °C at 1.30E+01 mm HgPhysProp
logP2.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.353 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
Mass Spec (NIST)Download (9.18 KB)
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Buffet M, Dupin N: Current treatments for scabies. Fundam Clin Pharmacol. 2003 Apr;17(2):217-25. Pubmed
External Links
ATC CodesNot Available
AHFS Codes
  • 84:04.12
PDB EntriesNot Available
FDA labelDownload (143 KB)
MSDSDownload (57 KB)
Interactions
Drug InteractionsNo interactions found.
Food InteractionsNot Available
Comments
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:09