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483-63-6 molecular structure
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N-ethyl-N-(2-methylphenyl)but-2-enamide

ChemBase ID: 150
Molecular Formular: C13H17NO
Molecular Mass: 203.28018
Monoisotopic Mass: 203.13101417
SMILES and InChIs

SMILES:
O=C(N(c1c(cccc1)C)CC)C=CC
Canonical SMILES:
CC=CC(=O)N(c1ccccc1C)CC
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

Cite this record

CBID:150 http://www.chembase.cn/molecule-150.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
N-ethyl-N-(2-methylphenyl)but-2-enamide
(2E)-N-ethyl-N-(2-methylphenyl)but-2-enamide
IUPAC Traditional name
eurax
crotamitonum
crotamiton
Brand Name
Crotamitex
Crotan
Eurasil
Eurax
Eurax Cream
Eurax Lotion
Euraxil
Veteusan
Synonyms
Crotamiton
N-Ethyl-o-crotonotoluidide
Crotamitone
Crotaglin
Crotalgin
Crotamiton
trans-Crotalgin
trans-Crotamitex
N-Ethyl-o-crotonotoluidide
trans-Crotamitone
Crotonyl N-ethyl-o-toluidine
trans-N-Crotonyl-N-ethyl-o-toluidine
(2E)-N-Ethyl-N-(2-methylphenyl)-2-butenamide
trans-Crotamiton
克罗米通
N-乙基-邻巴豆酰甲基苯胺
CAS Number
483-63-6
124236-29-9
EC Number
207-596-3
MDL Number
MFCD00026989
PubChem SID
160963613
24847834
46508599
PubChem CID
2883
688020
ATC CODE
QP53AX04
CHEMBL
1200709
Chemspider ID
599515
DrugBank ID
DB00265
KEGG ID
D01381
Unique Ingredient Identifier
D6S4O4XD0H
Wikipedia Title
Crotamiton

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 3.0881793  LogD (pH = 7.4) 3.0881796 
Log P 3.0881796  Molar Refractivity 64.1479 cm3
Polarizability 24.114462 Å3 Polar Surface Area 20.31 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 2.7  LOG S -2.76 
Solubility (Water) 3.53e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Boiling Point
153-155 °C/13 mmHg(lit.) expand Show data source
Flash Point
113 °C expand Show data source
235.4 °F expand Show data source
Density
0.987 g/mL at 25 °C(lit.) expand Show data source
Refractive Index
n20/D 1.54(lit.) expand Show data source
Hydrophobicity(logP)
2.9 expand Show data source
Storage Condition
Room Temperature (15-30°C) expand Show data source
RTECS
GQ7000000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-36/38-43 expand Show data source
R:22 expand Show data source
Safety Statements
26-36 expand Show data source
S:36/37/39 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H315-H317-H319 expand Show data source
GHS Precautionary statements
P280-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Pregnancy Category
C expand Show data source
Purity
97% expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Description
predominantly trans expand Show data source
Linear Formula
CH3CH=CHCON(C2H5)C6H4CH3 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00265 external link
Item Information
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
Sigma Aldrich - 128201 external link
Packaging
5 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 128201.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals - C818000 external link
Crotamiton is an anti-parasitic agent. Crotamiton is used both as a scabicidal (for treating scabies) and as a general antipruritic.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Buffet M, Dupin N: Current treatments for scabies. Fundam Clin Pharmacol. 2003 Apr;17(2):217-25. Pubmed
  • • Buffet, M. et al.: Fund. Clin. Pharmacol., 17, 217 (2003)
  • • Lemke, T.L.: Foye’s Prin. Med. Chem., 6, 1084 (2003)
  • • Dika, E. et al.: Cutan. Ocular Toxicol., 25, 211 (2003)
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PATENTS

PATENTS

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INTERNET

INTERNET

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