CAS 483-63-6|CAS 124236-29-9|Crotamiton|crotamitonum|N-ethyl-N-(2-methylphenyl)but-2-enamide|Eurax Cream|Eurax|Crotaglin|Veteusan|Eurasil|Crotamitone|Eurax Lotion|Crotan|Euraxil|Crotamitex|Crotalgin...

General Information

Structure

Molecular Formula

C₁₃H₁₇NO

Molecular Mass

203.28018

Exact Mass

203.13101417

Charge

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

InChIKey

DNTGGZPQPQTDQF-UHFFFAOYSA-N

Canonic Smiles

CC=CC(=O)N(c1ccccc1C)CC

Isomeric Smiles

O=C(N(c1c(cccc1)C)CC)C=CC

Calculated Properties

JChem

LogD (pH = 7.4)

3.09

LogD (pH = 5.5)

3.09

Log P

3.09

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

-0.60

Polar Surface Area

20.31

Polarizability

23.43

Molar Refractivity

64.15

LOG S

-3.38

Data Source

Names and Identifiers

IUPAC Traditional name

crotamitonum eurax crotamiton N-ethyl-o-crotonotoluidide

Synonyms

CrotamitonCrotaglinCrotamitoneCrotalginN-Ethyl-o-crotonotoluidide克罗米通N-乙基-邻巴豆酰甲基苯胺Crotamiton(2E)-N-Ethyl-N-(2-methylphenyl)-2-butenamidetrans-Crotamitontrans-Crotalgintrans-N-Crotonyl-N-ethyl-o-toluidinetrans-CrotamitoneCrotonyl N-ethyl-o-toluidinetrans-CrotamitexN-Ethyl-o-crotonotoluididecrotamitonecrotamitonN-ethyl-o-crotonotoluididecrotonyl-N-ethyl-o-toluidinecrotalgin

IUPAC name

N-ethyl-N-(2-methylphenyl)but-2-enamide (2E)-N-ethyl-N-(2-methylphenyl)but-2-enamide

Brand Name

EuraxEurasilVeteusanEurax CreamEuraxilCrotanEurax LotionCrotamitex

International Nonproprietary Name (INN)

crotamitonumcrotamiton

Names and Identifiers

Registration numbers

CAS Number

483-63-6124236-29-9

EC Number

207-596-3

PubChem CID

2883688020

PubChem SID

160963613248478344650859996079589

Unique Ingredient Identifier

Wikipedia Title

CHEMBL

KEGG ID

Chemspider ID

DrugBank ID

ATC CODE

MDL Number

Drug Central Database

744

MetaboLights Database

MTBLS1642MTBLS1918MTBLS1455MTBLS2406MTBLS2145

Patent number

CompTox Database

Beilstein Number

ACToR Database

KEGG DRUG Database

LINCS Database

CHEBI ID

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

2.9

Boiling Point

153-155 °C/13 mmHg(lit.)

Refractive Index

n20/D 1.54(lit.)

Flash Point

113 °C

235.4 °F

Density

0.987 g/mL at 25 °C(lit.)

Product Information

Certificate of Analysis

Download link

Purity

97%

Description

predominantly trans

Linear Formula

CH3CH=CHCON(C2H5)C6H4CH3

Pharmacology Properties

Pregnancy Category

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00265

Drug 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.

Indication

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

Pharmacology

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.

Affected Organisms

Humans and other mammals

Absorption

10 % absorbed when applied locally.

References

• Buffet M, Dupin N: Current treatments for scabies. Fundam Clin Pharmacol. 2003 Apr;17(2):217-25. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Molecule Details

References