Human Metabolome Database: Showing metabocard for Crotamiton (HMDB14410)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

3.6

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2017-03-02 21:33:11 UTC

HMDB ID

HMDB14410

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Crotamiton

Description

Crotamiton is only found in individuals that have used or taken this drug. It is a scabicidal and antipruritic agent available as a cream or lotion for topical use only. It is a colorless to slightly yellowish oil, having a faint amine-like odor. It is miscible with alcohol and with methanol.Crotamiton is an antiparasitic that is toxic to the scabies mite. Crotamiton also relieves itching by producing what is called a counter-irritation. As crotamiton evaporates from the skin, it produces a cooling effect. This cooling effect helps to divert your body's attention away from the itching.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Crotalgin	ChEBI
Crotamitone	ChEBI
Crotamitonum	ChEBI
Crotonyl-N-ethyl-O-toluidine	ChEBI
N-Ethyl-O-crotonotoluidide	ChEBI
Crotaglin	HMDB

Chemical Formula

C₁₃H₁₇NO

Average Molecular Weight

203.2802

Monoisotopic Molecular Weight

203.131014171

IUPAC Name

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

Traditional Name

eurax

CAS Registry Number

483-63-6

SMILES

CCN(C(=O)C=CC)C1=CC=CC=C1C

InChI Identifier

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

InChI Key

DNTGGZPQPQTDQF-UHFFFAOYSA-N

Chemical Taxonomy

Description

This compound belongs to the class of chemical entities known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Benzenoids

Sub Class

Benzene and substituted derivatives

Direct Parent

Anilides

Alternative Parents

Substituents

Anilide
Toluene
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

enamide (CHEBI:31439 )

Ontology

Status

Expected but not Quantified

Origin

Drug

Biofunction

Antiparasitic Agents
Antipruritics
Pesticides
Scabicides

Application

Pharmaceutical

Cellular locations

Membrane (predicted from logP)

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	3.53e-01 g/L	Not Available
LogP	2.9	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.35 mg/mL	ALOGPS
logP	2.7	ALOGPS
logP	3.09	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-0.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	64.15 m³·mol^-1	ChemAxon
Polarizability	23.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udi-0090000000-70e1ca34f13b9e4b9599	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0udi-1190000000-02218095d009d51f0b72	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-0gb9-9850000000-24da05acdd172bfde5f5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-9700000000-ae61a473efc6d72b8781	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-9600000000-6aaa881b4c06e68ed133	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-014i-9500000000-27cbd5bf3c121b56d6cc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-066u-9400000000-12ca412deed8c16a0f22	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-066u-9300000000-427f77529d09e1395f78	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-066u-9200000000-a03907e2130c0b4a1530	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biofluid Locations

Blood
Urine

Tissue Location

Not Available

Pathways

Not Available

Normal Concentrations

Biofluid	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Applicable	Not Available	Not Available	Taking drug identified by DrugBank entry DB00265	Not Applicable	details
Urine	Expected but not Quantified	Not Applicable	Not Available	Not Available	Taking drug identified by DrugBank entry DB00265	Not Applicable	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00265

DrugBank Metabolite ID

Not Available

Phenol Explorer Compound ID

Not Available

Phenol Explorer Metabolite ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

599515

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Crotamiton

NuGOwiki Link

HMDB14410

Metagene Link

HMDB14410

METLIN ID

Not Available

PubChem Compound

688020

PDB ID

Not Available

ChEBI ID

774660

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Buffet M, Dupin N: Current treatments for scabies. Fundam Clin Pharmacol. 2003 Apr;17(2):217-25. [PubMed:12667233 ]

Showing metabocard for Crotamiton (HMDB14410)

Structure for HMDB14410 (Crotamiton)