N-Ethyl-N-(2-methylphenyl)-2-butensäureamid

Bezeichnung:N-Ethyl-N-(2-methylphenyl)-2-butensäureamid

CAS-Nr483-63-6

Englisch Name:Crotamiton

CBNumberCB6451611

SummenformelC13H17NO

Molgewicht203.28

MOL-Datei483-63-6.mol

Synonyma

Crotamiton

N-Ethyl-N-(2-methylphenyl)-2-butensäureamid

N-Ethyl-N-(2-methylphenyl)-2-butensäureamid physikalisch-chemischer Eigenschaften

Schmelzpunkt	25°C
Siedepunkt	153-155 °C/13 mmHg (lit.)
Dichte	0.987 g/mL at 25 °C (lit.)
Brechungsindex	n20/D 1.54(lit.)
Flammpunkt	>230 °F
storage temp.	2-8°C
Löslichkeit	ethanol: soluble
pka	1.14±0.50(Predicted)
Aggregatzustand	<25°C Solid,>25°C Liquid
Farbe	Colourless to Light Brown
Wasserlöslichkeit	Soluble in water (1:500), alcohol, methanol, ether, and ethanol.
Merck	13,2622
Stabilität	Light Sensitive
InChIKey	DNTGGZPQPQTDQF-XBXARRHUSA-N
LogP	3.099 (est)
CAS Datenbank	483-63-6(CAS DataBase Reference)
NIST chemische Informationen	Crotamiton(483-63-6)
EPA chemische Informationen	Crotamiton (483-63-6)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	22-36/38-43
S-Sätze:	26-36
WGK Germany	3
RTECS-Nr.	GQ7000000
HS Code	2924296000

Gefahreninformationscode (GHS)

Crotamiton Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/38:Reizt die Augen und die Haut.
R43:Sensibilisierung durch Hautkontakt möglich.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
Crotamiton 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.
Beschreibung
Crotamiton 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.
Chemische Eigenschaften
N-Ethyl-o-crotonotoluidide is colourless or pale yellow, oily liquid
Originator
Eurax,Ciba Geigy,France,1949
Verwenden
Fungicide, insecticide.
Verwenden
antipruritic, scabicide
Verwenden
N-Ethyl-o-crotonotoluidide (Crotamiton) was used to treat scabies and various pruritic dermatoses.
Indications
Crotamiton (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.
Definition
ChEBI: 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.
Manufacturing Process
10.5 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).
Trademarks
Eurax (Westwood-Squibb).
Therapeutic Function
Scabicide
Clinical Use
N-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.
Nebenwirkungen
The most common side effect reported for crotamiton is skin irritation.
Veterinary Drugs and Treatments
Crotamiton 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 Upstream-Materialien And Downstream Produkte

N-Ethyl-N-(2-methylphenyl)-2-butensäureamid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

483-63-6, Crotamiton Verwandte Suche:

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