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Details

Stereochemistry ACHIRAL
Molecular Formula C13H17NO
Molecular Weight 203.2802
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CROTAMITON, (E)-

SMILES

CCN(C(=O)\C=C\C)C1=C(C)C=CC=C1

InChI

InChIKey=DNTGGZPQPQTDQF-XBXARRHUSA-N
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+

HIDE SMILES / InChI

Molecular Formula C13H17NO
Molecular Weight 203.2802
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Crotamiton is a scabicidal and antipruritic agent available as a cream or lotion for topical use. The drug was approved by FDA for the treatment of scabies and pruritic skin. Crotamiton is a mixture of the cis and trans isomers of N-ethyl-N-(o-methylphenyl)-2butenamide. Although the activity of crotamiton was shown both in vitro and in vivo, the mechanism of its action is still unknown.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
EURAX

Approved Use

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

Launch Date

1949
Palliative
EURAX

Approved Use

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

Launch Date

1949
PubMed

PubMed

TitleDatePubMed
The use of N-ethyl-o-crotonotoluidide in the treatment of scabies and various pruritic dermatoses.
1949 Jul
[Crotamiton and crotamiton hydrocortisone compounds in the treatment of pruritus].
1965 Aug 20
Crotamiton cream and lotion in the treatment of infants and young children with scabies.
1979
A single application of crotamiton lotion in the treatment of patients with pediculosis capitis.
1982 Dec
Crotamiton lotion in pruritus.
1984 Dec
Contact dermatitis due to crotamiton.
1986 Oct
The sensitizing capacity of crotamiton.
1988 May
Treatment of scabies with crotamiton.
1988 May
Contact dermatitis from crotamiton.
1992 Jul
Chromatography of crotamiton and its application to the determination of active ingredients in ointments.
1997 Jun
Treatment of scabies, permethrin 5% cream vs. crotamiton 10% cream.
2013
Topical ivermectin versus crotamiton cream 10% for the treatment of scabies.
2014 Jul
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:28:47 GMT 2023
Edited
by admin
on Fri Dec 15 15:28:47 GMT 2023
Record UNII
2EEH27851Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CROTAMITON, (E)-
Common Name English
TRANS-CROTAMITON
Common Name English
2-BUTENAMIDE, N-ETHYL-N-(2-METHYLPHENYL)-, (E)-
Systematic Name English
2-BUTENAMIDE, N-ETHYL-N-(2-METHYLPHENYL)-, (2E)-
Systematic Name English
Code System Code Type Description
FDA UNII
2EEH27851Y
Created by admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
PRIMARY
CAS
124236-29-9
Created by admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
PRIMARY
PUBCHEM
688020
Created by admin on Fri Dec 15 15:28:47 GMT 2023 , Edited by admin on Fri Dec 15 15:28:47 GMT 2023
PRIMARY