Crotamiton   Click here for help

GtoPdb Ligand ID: 11165

Synonyms: Eurax®
Approved drug
Crotamiton is an approved drug (FDA (1955), UK (1997))
Compound class: Synthetic organic
Comment: Crotamiton is a drug, available as a cream or lotion for topical use only, that is used both as a scabicidal (for treating scabies) and as a general antipruritic (anti-itching drug).
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 20.31
Molecular weight 203.13
XLogP 2.88
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES C/C=C/C(=O)N(c1ccccc1C)CC
Isomeric SMILES C/C=C/C(=O)N(c1ccccc1C)CC
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+
InChI Key DNTGGZPQPQTDQF-XBXARRHUSA-N
Bioactivity Comments
Scabicidal agent with unknown mechanism of action. The mechanism of action of crotamiton as a general antipruritic has been reported in which crotamiton inhibits TRPV4 (transient receptor potential vanilloid 4) channel that is expressed in the skin and primary sensory neuron [1].
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
TRPV4 N/A Inhibitor Inhibition - - - 1
⤷ [1]
Description: Whole-cell patch-clamp recordings, crotamiton strongly inhibited TRPV (vanilloid) 4 channels followed by large currents after crotamiton washout.