Crotamiton

Crotamiton Basic information
Product Name:Crotamiton
Synonyms:(2E)-N-Ethyl-N-(2-methylphenyl)-2-butenamide;2-Butenamide, N-ethyl-N-(2-methylphenyl)-;component of Eurax;Crotalgin;Crotamitex;Crotamitone;Eurasil;Eurax
CAS:483-63-6
MF:C13H17NO
MW:203.28
EINECS:207-596-3
Product Categories:EURAX;API's;APIs
Mol File:483-63-6.mol
Crotamiton Structure
Crotamiton Chemical Properties
Melting point 25°C
Boiling point 153-155 °C/13 mmHg (lit.)
density 0.987 g/mL at 25 °C (lit.)
refractive index n20/D 1.54(lit.)
Fp >230 °F
storage temp. 2-8°C
solubility ethanol: soluble
pka1.14±0.50(Predicted)
form neat
color Colourless to Light Brown
Water Solubility Soluble in water (1:500), alcohol, methanol, ether, and ethanol.
Merck 13,2622
Stability:Light Sensitive
InChIKeyDNTGGZPQPQTDQF-XBXARRHUSA-N
LogP3.099 (est)
CAS DataBase Reference483-63-6(CAS DataBase Reference)
NIST Chemistry ReferenceCrotamiton(483-63-6)
EPA Substance Registry SystemCrotamiton (483-63-6)
Safety Information
Hazard Codes Xn
Risk Statements 22-36/38-43
Safety Statements 26-36
WGK Germany 3
RTECS GQ7000000
HS Code 2924296000
MSDS Information
ProviderLanguage
N-Ethyl-N-(2-methylphenyl)-butenamide English
SigmaAldrich English
Crotamiton Usage And Synthesis
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.
DescriptionCrotamiton is an ectoparasiticide and antipruritic agent. It blocks the mouse transient receptor potential vanilloid 4 (TRPV4) channel expressed in HEK293 cells in a calcium-dependent manner (IC50s = 223.5 and 15.5 μM in buffer containing 0 and 2 mM calcium, respectively). It inhibits scratching behavior in mice induced by the TRPV4 agonist GSK1016790A . Topical application of crotamiton (0.025 g of a 10% ointment) also inhibits scratching behavior in mice induced by histamine, serotonin , and the proteinase-activated receptor 2 (PAR2) agonist SLIGRL-NH2 . Formulations containing crotamiton have been used to eradicate scabies and in the treatment of symptomatic pruritic skin.
Chemical PropertiesN-Ethyl-o-crotonotoluidide is colourless or pale yellow, oily liquid
OriginatorEurax,Ciba Geigy,France,1949
UsesN-Ethyl-o-crotonotoluidide (Crotamiton) was used to treat scabies and various pruritic dermatoses.
Usesantipruritic, scabicide
UsesFungicide, insecticide.
DefinitionChEBI: The amide resulting from the formal condensation of crotonic acid with N-ethyl-2-methylaniline. A colourless or pale yellow oily liquid, it is used in the treatment of pruritus (itching) by producing a counter-irritation: as it evaporate from the skin, it produces a cooling effect that diverts attention away from the itching. It has also been used as an acaricide in the treatment of scabies, though more effective drugs are usually preferred.
IndicationsCrotamiton (N-ethyl-o-crotonotoluide, Eurax) is a synthetic chloroformate salt used for the prevention and treatment of scabies, although cure rates tend to be lower for the same number of applications compared with lindane and permethrin. It may have an antipruritic effect independent of its scabetic effect. Its mechanism of action is unknown. It is not effective as a pediculicide.
Crotamiton (10% N-ethyl-o-crotonotoluide, Eurax) cream applied twice and left on during a 48-hour period is usually effective against scabies and has been reported to act as an antipruritic agent.
Manufacturing Process10.5 parts of crotonyl chloride are dropped in such a manner into 27 parts of N-ethyl-o-toluidine, white stirring, that the temperature rises to 130° to 140°C. After cooling, the reaction product is dissolved in ether or other solvent that is immiscible with water, and the solution is washed successively with hydrochloric acid, alkali solution and water. After distilling off the solvent, the residue is distilled in vacuo. The crotonic acid N-ethyl-o-toluidide boils at 153° to 155°C at a pressure of 13 mm and is a slightly yellowish oil. Instead of carrying the reaction out in the presence of an excess of N-ethyl-otoluidine, it may be carried out in the presence of an acid-combining agent, for example, potash, advantageously in a solvent (e.g., acetone).
Brand nameEurax (Westwood-Squibb).
Therapeutic FunctionScabicide
Clinical UseN-Ethyl-N-(2-methylphenyl)-2-butenamide, or N-ethyl-ocrotonotoluidide(Eurax), is a colorless, odorless oily liquid.It is virtually insoluble in water but soluble in most organicsolvents.
Crotamiton is available in 10% concentration in a lotionand a cream intended for the topical treatment of scabies. Its antipruritic effect is probably because of a local anestheticaction.
Side effectsThe most common side effect reported for crotamiton is skin irritation.
Veterinary Drugs and TreatmentsCrotamiton is a topical miticide/scabicide and has been used primarily for adjunctive treatment (with ivermectin) for treating mite infections (e.g., Knemidopkoptes) in birds. Crotamiton has both miticidal and antipruritic actions, but the mechanism for each is not known.
Crotamiton Preparation Products And Raw materials
Raw materialsDiethyl sulfate-->Crotonic acid-->Crotonic acid-->2-Ethylaminotoluene-->(E)-2-Butenoyl chloride
Trinexapac-ethyl Ethanol N-Methylaniline Methyl 2-hydroxyethyl cellulose 3,3',5,5'-Tetramethylbenzidine dihydrochloride 2-Ethylaniline 3-Diethylaminophenol 2-Butanone Ethylparaben Crotamiton ISOXADIFEN-ETHYL N-Ethylaniline N,N-Dimethylaniline Ethyl acetate 1-(4-CHLOROBENZYL)-4,8-DIMETHYL-2(1H)-QUINOLINONE Ethyl propiolate Ethyl acrylate Ethyl cyanoacetate

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