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
Eurax
External IDs Not Available
Product Ingredients Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EuraxCream100 mg/gTopicalRanbaxy Inc.2008-12-15Not applicableUs
EuraxLotion100 mg/gTopicalRanbaxy Inc.2008-11-13Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Eurax Cream 10%Cream10 %TopicalColumbia Laboratories1953-12-31Not applicableCanada
Unapproved/Other Products Not Available
International Brands
NameCompany
CrotamitexGepepharm
EuracinGreen Cross (South Korea)
Brand mixturesNot Available
Categories
UNII2EEH27851Y
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
Pharmacology
Indication

For eradication of scabies (Sarcoptes scabiei) and for symptomatic treatment of pruritic skin.

Structured Indications
Pharmacodynamics

Crotamiton 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 action

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.

Related Articles
Absorption

10 % 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
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions No interactions found.
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Buffet M, Dupin N: Current treatments for scabies. Fundam Clin Pharmacol. 2003 Apr;17(2):217-25. [PubMed:12667233 ]
External Links
ATC CodesNot Available
AHFS Codes
  • 84:04.12
PDB EntriesNot Available
FDA labelDownload (143 KB)
MSDSDownload (57 KB)
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
Manufacturers
  • Ranbaxy laboratories inc
  • Summers laboratories inc
Packagers
Dosage forms
FormRouteStrength
CreamTopical100 mg/g
LotionTopical100 mg/g
CreamTopical10 %
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 (°C)< 25 °CPhysProp
boiling point (°C)154 °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 RuleNoChemAxon
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 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9461
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Download (9.18 KB)
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-0090000000-70e1ca34f13b9e4b9599View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0udi-1190000000-02218095d009d51f0b72View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0gb9-9850000000-24da05acdd172bfde5f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9700000000-ae61a473efc6d72b8781View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9600000000-6aaa881b4c06e68ed133View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-014i-9500000000-27cbd5bf3c121b56d6ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-066u-9400000000-12ca412deed8c16a0f22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-066u-9300000000-427f77529d09e1395f78View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-066u-9200000000-a03907e2130c0b4a1530View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentAnilides
Alternative ParentsToluenes / Tertiary carboxylic acid amides / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
SubstituentsAnilide / Toluene / Tertiary carboxylic acid amide / Carboxamide group / Carboxylic acid derivative / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptorsenamide (CHEBI:31439 )
Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 16:47