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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
SaltsNot Available
Brand names
NameCompany
CrotamitexGepepharm
EuracinGreen Cross (South Korea)
EuraxRanbaxy Laboratories (US), Novartis (UK)
Brand mixturesNot 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
Mass Specshow(9.18 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassAnilides
Direct parentAnilides
Alternative parentsToluenes; Tertiary Carboxylic Acid Amides; Enones; Tertiary Amines; Polyamines; Enolates; Carboxylic Acids
Substituentstoluene; enone; tertiary carboxylic acid amide; tertiary amine; carboxamide group; carboxylic acid derivative; enolate; polyamine; carboxylic acid; amine; organonitrogen compound
Classification descriptionThis compound belongs to the anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
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
Metabolism
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
Property Value Probability
Human Intestinal Absorption + 0.9905
Blood Brain Barrier + 0.9939
Caco-2 permeable + 0.8303
P-glycoprotein substrate Non-substrate 0.788
P-glycoprotein inhibitor I Non-inhibitor 0.8611
P-glycoprotein inhibitor II Non-inhibitor 0.709
Renal organic cation transporter Non-inhibitor 0.8494
CYP450 2C9 substrate Non-substrate 0.7767
CYP450 2D6 substrate Non-substrate 0.6383
CYP450 3A4 substrate Substrate 0.586
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9461
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.831
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7792
Ames test Non AMES toxic 0.7386
Carcinogenicity Carcinogens 0.5946
Biodegradation Not ready biodegradable 0.9764
Rat acute toxicity 2.1007 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9726
hERG inhibition (predictor II) Non-inhibitor 0.8168
Pharmacoeconomics
Manufacturers
  • Ranbaxy laboratories inc
  • Summers laboratories inc
Packagers
Dosage forms
FormRouteStrength
CreamTopical
Prices
Unit descriptionCostUnit
Eurax 10% Lotion 454 gm Bottle353.03USDbottle
Eurax 10% Lotion 60 gm Bottle54.21USDbottle
Eurax 10% Cream 60 gm Tube51.99USDtube
Eurax 10% cream0.27USDg
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 Solubility0.353ALOGPS
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 RuleNoChemAxon
Spectra
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
ResourceLink
KEGG DrugD01381
PubChem Compound688020
PubChem Substance46508599
ChemSpider2780
PharmGKBPA164745460
Drug Product Database623377
RxListhttp://www.rxlist.com/cgi/generic3/crotamiton.htm
Drugs.comhttp://www.drugs.com/cdi/crotamiton-cream.html
WikipediaCrotamiton
ATC CodesNot Available
AHFS Codes
  • 84:04.12
PDB EntriesNot Available
FDA labelshow(143 KB)
MSDSshow(57 KB)
Interactions
Drug InteractionsSearched, but no 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