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Crotamiton

Clinical data
AHFS/Drugs.com	Monograph
ATCvet code	QP53AX04 (WHO)
Identifiers
IUPAC name (E)-N-Ethyl-N-(2-methylphenyl)but-2-enamide
CAS Number	483-63-6
PubChem CID	688020
DrugBank	DB00265
ChemSpider	599515
UNII	D6S4O4XD0H
KEGG	D01381
ChEMBL	ChEMBL1200709
CompTox Dashboard (EPA)	DTXSID6040664
ECHA InfoCard	100.006.907
Chemical and physical data
Formula	C13H17NO
Molar mass	203.285 g·mol
3D model (JSmol)	Interactive image
SMILES O=C(N(c1ccccc1C)CC)/C=C/C
InChI 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+ Key:DNTGGZPQPQTDQF-XBXARRHUSA-N
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Crotamiton is a drug that is used both as a scabicidal (for treating scabies) and as a general antipruritic (anti-itching drug). It is a prescription, lotion-based medicine that is applied to the whole body to get rid of the scabies mite that burrows under the skin and causes itching.

Use

For treating scabies, crotamiton should be applied to the whole body rather than a localized area. It is applied two or three times, with a 24-hour delay between applications, and the patient is asked to take a shower no sooner than after 48 hours. For children under 3 years, it is applied once daily. It can also be used to treat itching stemming from other causes, e.g. insect bites, in which case it is applied to the itching areas only, and repeated if necessary after 4 to 8 hours. Use near the eyes, or breaks in the skin, should be avoided.

Pharmacology

Crotamiton is toxic to the scabies mite. It probably acts as a general antipruritic by inhibition of TRPV4, a sensory ion channel that is expressed in the skin and primary sensory neurons.

Pharmacokinetics

After topical application, crotamiton is absorbed systemically. It has an elimination half-life of 30.9 hours and 4.8-8.8% is excreted in the urine.

Side effects

The most common side effect of crotamiton is skin irritation.

Trade name

Crotamiton is marketed under the trade names Eurax, which is manufactured by Ranbaxy Laboratories in the United States, and GlaxoSmithKline in the United Kingdom, and Euracin, which is manufactured by Green Cross in South Korea. In Germany, it is marketed under the brand name Crotamitex. In India, it is sold as Eurax by Ranbaxy Laboratories.

References

1. "Crotamiton: mechanism of action". Medscape Drug Information.
2. Kittaka H, Yamanoi Y, Tominaga M (October 2017). "Transient receptor potential vanilloid 4 (TRPV4) channel as a target of crotamiton and its bimodal effects". Pflügers Archiv. 469 (10): 1313–1323. doi:10.1007/s00424-017-1998-7. PMID 28612138. S2CID 4059914.
3. "Crotamiton: pharmacokinetics". Medscape Drug Information.

• Anti-infective agents
• Antipruritics
• Anilides
• 2-Tolyl compounds