Crotamiton CAS 483-63-6
Introduction：Basic information about Crotamiton CAS 483-63-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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 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 | n |
| Fp | >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 |
| Major Application | pharmaceutical |
| Cosmetics Ingredients Functions | SOLVENT ANTIMICROBIAL |
| InChI | 1S/C13H17NO/c1-4-8-13(15)14(5-2)12-10-7-6-9-11(12)3/h4,6-10H,5H2,1-3H3/b8-4+ |
| InChIKey | DNTGGZPQPQTDQF-XBXARRHUSA-N |
| SMILES | CCN(C(=O)\C=C\C)c1ccccc1C |
| 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) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 22-36/38-43 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| RTECS | GQ7000000 |
| HS Code | 2924296000 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral |
| Description | Crotamiton is available as a 10% cream for the treatment of scabies, although it is less effectivethan pyrethrins or permethrin. Because crotamiton may need to be applied a second timefor 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 crotamitonover lindane comes from the fact that lindane has potential neurotoxicity if absorbed especially ininfants 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 usedfor the prevention and treatment of scabies, although cure rates tend to be lowerfor the same number of applications compared with lindane and permethrin. It mayhave an antipruritic effect independent of its scabetic effect. Its mechanism of actionis unknown. It is not effective as a pediculicide. Crotamiton (10% N-ethyl-o-crotonotoluide, Eurax) cream applied twice andleft on during a 48-hour period is usually effective against scabies and has beenreported to act as an antipruritic agent. |
| Manufacturing Process | 10.5 parts of crotonyl chloride are dropped in such a manner into 27 parts ofN-ethyl-o-toluidine, white stirring, that the temperature rises to 130° to140°C. After cooling, the reaction product is dissolved in ether or othersolvent that is immiscible with water, and the solution is washed successivelywith 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 at153° to 155°C at a pressure of 13 mm and is a slightly yellowish oil. Insteadof 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 sideeffect 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 miteinfections (e.g., Knemidopkoptes) in birds. Crotamiton has both miticidal and antipruritic actions, but the mechanism for each is notknown. |
| References | [1] MOHAMAD GOLDUST MS Ramin R M Elham Rezaee MD. Topical ivermectin versus crotamiton cream 10% for the treatment of scabies[J]. International Journal of Dermatology, 2014, 53 7: 904-908. DOI: 10.1111/ijd.12447 [2] HIROKI KITTAKA Makoto T Yu Yamanoi. Transient receptor potential vanilloid 4 (TRPV4) channel as a target of crotamiton and its bimodal effects.[J]. Pflugers Archiv?: European journal of physiology, 2017, 469 10: 1313-1323. DOI: 10.1007/s00424-017-1998-7 [3] RIKA SEKINE. Anti pruritic effects of topical crotamiton, capsaicin, and a corticosteroid on pruritogen-induced scratching behavior[J]. Experimental Dermatology, 2011, 21 3: 201-204. DOI: 10.1111/j.1600-0625.2011.01433.x |
Crotamiton Preparation Products And Raw materials
| Raw materials | Diethyl sulfate-->Crotonic acid-->Crotonic acid-->N-Ethyl-o-toluidine-->(E)-2-Butenoyl chloride |
