Crotamiton

Product Name: Crotamiton
CAS No.: 483-63-6
Chemical Name: Crotamiton
Synonyms: N-ETHYL-O-CROTONOTOLUIDIDE;Eurax;Crotalgin;n-ethyl-n-(2-methylphenyl)-butenamide;Eurasil;Euraxil;Veteusan;Crotamtex;Vet-eusan;Clomitone
CBNumber: CB6451611
Molecular Formula: C13H17NO
Formula Weight: 203.28
MOL File: 483-63-6.mol

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Crotamiton Property

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.)
Flash point:: >230 °F
storage temp.: 2-8°C
solubility: ethanol: soluble
pka: 1.14±0.50(Predicted)
form: <25°C Solid,>25°C Liquid
color: Colourless to Light Brown
Water Solubility: Soluble in water (1:500), alcohol, methanol, ether, and ethanol.
Merck: 13,2622
Stability:: Light Sensitive
InChIKey: DNTGGZPQPQTDQF-XBXARRHUSA-N
LogP: 3.099 (est)
CAS DataBase Reference: 483-63-6(CAS DataBase Reference)
NIST Chemistry Reference: Crotamiton(483-63-6)
EPA Substance Registry System: Crotamiton (483-63-6)

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Safety

Hazard Codes: Xn
Risk Statements: 22-36/38-43
Safety Statements: 26-36
WGK Germany: 3
RTECS: GQ7000000
HS Code: 2924296000

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 128201
Product name: N-Ethyl-o-crotonotoluidide
Purity: 97%
Packaging: 5g
Price: $60.1
Updated: 2024/03/01

Sigma-Aldrich

Product number: 1151006
Product name: Crotamiton
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 200mg
Price: $436
Updated: 2024/03/01

Sigma-Aldrich

Product number: BP094
Product name: Crotamiton
Purity: British Pharmacopoeia (BP) Reference Standard
Packaging: 100MG
Price: $221
Updated: 2023/06/20

Sigma-Aldrich

Product number: C2970000
Product name: Crotamiton
Purity: European Pharmacopoeia (EP) Reference Standard
Packaging: c2970000
Price: $220
Updated: 2024/03/01

Cayman Chemical

Product number: 23943
Product name: Crotamiton
Packaging: 100mg
Price: $32
Updated: 2024/03/01

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Crotamiton Chemical Properties,Usage,Production

Description

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.

Description

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.

Chemical Properties

N-Ethyl-o-crotonotoluidide is colourless or pale yellow, oily liquid

Originator

Eurax,Ciba Geigy,France,1949

Uses

N-Ethyl-o-crotonotoluidide (Crotamiton) was used to treat scabies and various pruritic dermatoses.

Uses

antipruritic, scabicide

Uses

Fungicide, insecticide.

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.

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.

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).

brand name

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.

Side effects

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 Preparation Products And Raw materials

Raw materials

TRANS-2-BUTENOIC ACID Crotonic acid Diethyl sulfate

Preparation Products

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Crotamiton Suppliers

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View Lastest Price from Crotamiton manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd

Product: Crotamiton 483-63-6
Price: US $75.00-25.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 20ton
Release date: 2024-05-27

Hebei Mujin Biotechnology Co.,Ltd

Product: Crotamiton 483-63-6
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 50000KG/month
Release date: 2023-06-30

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Crotamiton 483-63-6
Price: US $0.00/Kg/Drum
Min. Order: 1KG
Purity: 99%min
Supply Ability: 500kg
Release date: 2021-09-11

483-63-6, CrotamitonRelated Search:

3,3',5,5'-Tetramethylbenzidine dihydrochloride 2-Ethylaniline Ethyl propiolate N,N-Dimethylaniline Trinexapac-ethyl N-Ethylaniline ISOXADIFEN-ETHYL N-Methylaniline Methyl 2-hydroxyethyl cellulose 3-Diethylaminophenol Ethyl acetate Ethyl acrylate Ethyl cyanoacetate Ethanol Ethylparaben Potassium clavulanate 2-Butanone CROTAMITON IMPURITY A

(2E)-N-Ethyl-N-(2-methylphenyl)-2-butenamide

2-Butenamide, N-ethyl-N-(2-methylphenyl)-

component of Eurax

Crotalgin

Crotamitex

Crotamitone

Eurasil

Eurax

Euraxil

n-ethyl-n-(2-methylphenyl)-2-butenamid

n-ethyl-n-(2-methylphenyl)-2-butenamide

N-ETHYL-O-CROTONOTOLUIDINE (CROTAMITON)

N-ETHYL-2-CROTONOTOLUIDINE(CROTAMITON)

ORTHO-CROTONOTOLUIDIDE,N-ETHYL-

Crotamtex

N-Crotonyl-N-ethyl-o-toluidine

trans-N-Ethyl-N-(o-tolyl)-2-butenamide

EURAX (crotaMiton)

Crotamiton (200 mg)

CrotaMiton (Cis/Trans Mixture)

N-ethyl-N-(2-methylphenyl)but-2-enamide

Crotamiton ImpuritⅠ:N-ethyl-N-(2-tolyl)-3-butenamide

(E)-N-ethyl-N-(2-methylphenyl)-2-butenamide

n-ethyl-o-crotonotoluidid

N-Ethyl-ortho-crotonotoluidide

o-Crotonotoluidide, N-ethyl-

Veteusan

Vet-eusan

n-ethyl-n-(2-methylphenyl)-butenamide

N-ETHYL-O-CROTONOTOLUIDE

N-ETHYL-O-CROTONOTOLUIDIDE

N-ETHYL-O-CROTONOTOLUIDINE

N-ETHYL-2-CROTONYL METHYL ANILINE

LABOTEST-BB LT00244806

CROTAMITON

CROTAMITONUM

CROTONYL N-ETHYL-O-TOLUIDINE

BUT-2-ENOIC ACID ETHYL-2-TOLYLAMIDE

N-ethylcroton-o-toluidide

N-Ethyl-o-crotonotoluidide,predominantly trans

N-ETHYL-O-CROTONOTOLUIDIDE, 97%, PREDOMI NANTLY TRANS

N-Ethyl-2-crotonyl

CROTAMITON,BP

Crotamiton CRS

Crotamiton USP/EP/BP

crotamitor

Crotamiton (1151006)

N-Ethyl-N-(o-tolyl)but-2-enamide

N-ethyl-N-(2-methylphenyl)but-2-enamidez

Clomitone

CrotamitonCrotamiton (cis/trans Mixture)

Crotamiton, 10 mM in DMSO

(E)-N-ethyl-N-(2-methylphenyl)but-2-enamide

Crotamiton (Mixture of Z and E Isomers)

483-63-6

483-65-6

CH3CHCHCONC2H5C6H4CH3

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