Crotamiton

Structural formula
	Mixture of the ( E ) and ( Z ) isomer - Figure shows the ( E ) isomer
General
Non-proprietary name	Crotamiton
other names	N -ethyl- o -crotonotoluidine; N -ethyl- N - (2-methylphenyl) -2-butenamide; Eurax;
Molecular formula	C 13 H 17 NO
Brief description	colorless to pale yellow, oily liquid with a slight amine odor
External identifiers / databases
EC number	806-597-1
ECHA InfoCard	100,233,700
PubChem	688020
ChemSpider	599515
DrugBank	DB00265
Wikidata	Q2439845
Drug information
ATC code	D04 AX ; Q P53AX04 ;
properties
Molar mass	203.28 g mol −1
density	0.987 g cm −3
boiling point	153-155 ° C
Refractive index	1.54 (20 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-315-317-319
	P: 280-305 + 351 + 338
Toxicological data	1500 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Crotamiton is a medicine used to treat scabies . It was patented in 1949 as an antipruriginous drug and works against both the grave mites that cause it and the itching .

Isomerism

Crotamiton is a mixture of ( E ) -isomer [synonym: trans -isomer] and ( Z ) -isomer [synonym: cis -isomer]. The ( Z ) -isomer content must not exceed 15%.

Extraction and presentation

Crotamiton is produced by reacting crotonic acid chloride with N -ethyl-2-methylaniline.

Application in veterinary medicine and trade names

In Germany, no crotamiton-based veterinary drugs are approved. In Austria, the active ingredient for the treatment of sarcoptic mange in dogs is sold under the trade name Veteusan . The use of crotamiton in food-producing animals is not permitted in the EU, as the active ingredient is not listed in Regulation (EU) No. 37/2010 .

Individual evidence

↑ Entry on Crotamiton in Pharmawiki , accessed on January 28, 2017.
↑ ^a ^b ^c ^d ^e data sheet N-Ethyl-o-crotonotoluidide from Sigma-Aldrich , accessed on January 26, 2014 ( PDF ).
↑ ^a ^b Entry on Crotamiton. In: Römpp Online . Georg Thieme Verlag, accessed on February 17, 2014.
^ European Pharmacopoeia , Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, pp. 2221–2222, ISBN 978-3-7692-3962-1 .

[Pharmawiki-1] Entry on Crotamiton in Pharmawiki , accessed on January 28, 2017.

[fluka-2] ↑ ^a ^b ^c ^d ^e data sheet N-Ethyl-o-crotonotoluidide from Sigma-Aldrich , accessed on January 26, 2014 ( PDF ).

[roempp-3] Entry on Crotamiton. In: Römpp Online . Georg Thieme Verlag, accessed on February 17, 2014.

[EuropäischesArzneibuch-4] European Pharmacopoeia , Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, pp. 2221–2222, ISBN 978-3-7692-3962-1 .