Crotamiton

Identification

Name
Crotamiton
Accession Number
DB00265  (APRD00211)
Type
Small Molecule
Groups
Approved
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
Not Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
EuraxCream100 mg/gTopicalRanbaxy Inc.2008-12-15Not applicableUs
EuraxLotion100 mg/gTopicalRanbaxy Inc.2008-11-13Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Eurax Cream 10%Cream10 %TopicalColumbia Laboratories1953-12-31Not applicableCanada
International/Other Brands
Crotamitex (Gepepharm) / Euracin (Green Cross (South Korea)) / Eurax
Categories
UNII
2EEH27851Y
CAS number
483-63-6
Weight
Average: 203.2802
Monoisotopic: 203.131014171
Chemical Formula
C13H17NO
InChI Key
DNTGGZPQPQTDQF-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.

Absorption

10 % absorbed when applied locally.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
No interactions found.
Food Interactions
Not Available

References

General References
  1. Buffet M, Dupin N: Current treatments for scabies. Fundam Clin Pharmacol. 2003 Apr;17(2):217-25. [PubMed:12667233]
External Links
KEGG Drug
D01381
PubChem Compound
2883
PubChem Substance
46508599
ChemSpider
599515
ChEMBL
CHEMBL1200709
PharmGKB
PA164745460
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Crotamiton
AHFS Codes
  • 84:04.12 — Scabicides and Pediculicides
FDA label
Download (143 KB)
MSDS
Download (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.
Patents
Not Available

Properties

State
Liquid
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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-0090000000-70e1ca34f13b9e4b9599
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0udi-1190000000-02218095d009d51f0b72
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0gb9-9850000000-24da05acdd172bfde5f5
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-9700000000-ae61a473efc6d72b8781
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-9600000000-6aaa881b4c06e68ed133
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-014i-9500000000-27cbd5bf3c121b56d6cc
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-066u-9400000000-12ca412deed8c16a0f22
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-066u-9300000000-427f77529d09e1395f78
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-066u-9200000000-a03907e2130c0b4a1530

Taxonomy

Description
This compound belongs to the class of organic compounds 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Anilides
Direct Parent
Anilides
Alternative Parents
Toluenes / Tertiary carboxylic acid amides / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Anilide / Toluene / Tertiary carboxylic acid amide / Carboxamide group / Carboxylic acid derivative / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
enamide (CHEBI:31439)

Drug created on June 13, 2005 07:24 / Updated on January 15, 2018 08:40