Basic information
- CAS
483-63-6- Standard SMILES
CC=CC(=O)N(CC)c1ccccc1C- InChIKey
DNTGGZPQPQTDQF-UHFFFAOYSA-N- Molecular formula
- C13H17NO
- Average molar mass
- 203.28 g/mol
- Monoisotopic mass
- 203.13101417
Overview
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.
Names & identifiers
- Preferred name
- Crotamiton
- IUPAC
- N-ethyl-N-(2-methylphenyl)but-2-enamide
- English name
- Crotamiton
- Molecular formula
- C13H17NO
- Molecular weight
- 203.28
Names & synonyms
CrotanN-ethyl-N-(2-methylphenyl)but-2-enamideDTXSID6040664CrotamitoneCrotalginCrotamitonumD6S4O4XD0HDTXCID4020664CHEBI:31439NSC-758951RefChem:58614N-ethylcrotono-o-toluidide
Show more names
N-ETHYL-O-CROTONOTOLUIDIDEn-ethyl-n-(2-methylphenyl)-butenamideEurasilEuraxilVeteusanCrotamtexVet-eusanClomitone
207-596-32-Butenamide, N-ethyl-N-(2-methylphenyl)-483-63-6Crotamitoncrotonyl-N-ethyl-o-toluidineEuraxCrotamiton (Cis/Trans Mixture)N-ethyl-N-(o-tolyl)but-2-enamide
Database identifiers
- CAS
483-63-6- PubChem CID
- 2883
- DTXSID
DTXSID6040664- ChEMBL
CHEMBL3183440- EC Number
- 207-596-3
Properties
Computed structural properties
- XLogP
- 2.8
- Topological polar surface area
- 20.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 3
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 235
Experimental & physicochemical properties
LogP2.9
Solubility3.53e-01 g/L
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point
< 25 °C
< 25 °C
Physical DescriptionSolid
Collision Cross Section157.0 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID6040664]
Physicochemical properties
- Melting point
- 25 °C · 25°C
- Boiling point
- 153 · 153-155 °C/13 mmHg (lit.)
- Density
- 0.987 g/mL · 0.987 g/mL at 25 °C (lit.)
- refractive index
- 20 · n 20/D 1.54 (lit.)
- Flash point
- 113 °C · 113 °C - closed cup
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P272, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 52 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety InformationIMAP assessments - 2-Butenamide, N-ethyl-N-(2-methylphenyl)-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- 3
- rtecs
- GQ7000000
- hs_code
- 2924296000
- risk_code
- 22-36/38-43
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P264-P270-P301+P312-P501
Chemistry & industry
Pharmacology
ATC CodeQP - Antiparasitic products, insecticides and repellents
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.
MeSH Pharmacological ClassificationChemicals used to destroy pests of any sort. The concept includes fungicides (FUNGICIDES, INDUSTRIAL); INSECTICIDES; RODENTICIDES; etc.
Absorption, Distribution and Excretion10 % absorbed when applied locally.
Cellular LocationsMembrane
Uses & manufacturing
UsesUse (kg; approx.) in Germany (2009): >100
Applications
DescriptionCrotamiton is available as a 10% cream for the treatment of scabies, although it is less effective than pyrethrins or permethrin. Because crotamiton may need to be applied a second time for successful treatment of scabies but the pyrethrins or permethrin require a single application, poor patient compliance with crotamiton may reduce its effectiveness. The advantage of crotamiton over lindane comes from the fact that lindane has potential neurotoxicity if absorbed especially in infants and children, whereas crotamiton has less systemic neurotoxicity.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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