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Identification
NameBenzyl Benzoate
Accession NumberDB00676  (APRD00821, DB02775, EXPT00792)
Typesmall molecule
Groupsapproved
Description

Benzyl benzoate is one of the older preparations used to treat scabies. Scabies is a skin infection caused by the mite sarcoptes scabiei. It is characterised by severe itching (particularly at night), red spots, and may lead to a secondary infection. Benzyl benzoate is lethal to this mite and so is useful in the treatment of scabies. It is also used to treat lice infestation of the head and body. Benzyl benzoate is not the treatment of choice for scabies due to its irritant properties.

Structure
Thumb
Synonyms
SynonymLanguageCode
AcarobenzylNot AvailableIS
BenylateNot AvailableNot Available
BenzevanNot AvailableIS
Benzoate de benzyleFrenchINN
BenzoesäurebenzylesterNot AvailableIS
BENZOIC acid phenylmethylesterNot AvailableNot Available
Benzoic acid, benzyl esterNot AvailableNot Available
Benzoic acid, phenylmethyl esterNot AvailableNot Available
Benzyl benzoatGermanINN
Benzylis benzoasLatinINN
Phenylmethyl benzoateNot AvailableNot Available
SpasmodineNot AvailableIS
SaltsNot Available
Brand names
NameCompany
Acaril-SMedifarma
AcarilbialBial
AcarsanBiosintética
AcilDidy Pharmaceutical
AntiscabiosumStrathmann
Antiscabiosum für KinderStrathmann
AscabiolSanofi-Aventis
AscalolPharmaghreb
B.B. LotionWashington
BE BOAesculap
BenzalcorCorsalud
BenzilbenzoatLabor
BenzogalRafarm
BenzotalGrindeks
BezoMedisearch
FinsarnaQualicont
GensarnaGencopharmaceutical
MiticocanAché
NovoscabinPolon
OpeleBeta Health Care
PharcobenzylPharco
SanasarKley Hertz
SaniscabisNeo-Fármaco
ScabiconMedicon
ScabiexRekah
ScabinAbdi Ibrahim
ScabisolJayson
ScabitoxBosnalijek
TekoceJadran
ZilabenCristália
Brand mixtures
Brand NameIngredients
AcarilBenzyl Benzoate and Sulfur
DermadexBenzoic Acid + Benzyl Benzoate + Lindane + Salicylic Acid + Zinc Oxide + Zinc Undecylenate
SarnacurBenzyl Benzoate and Benzocaine
TenutexBenzyl Benzoate and Disulfiram
Categories
CAS number120-51-4
WeightAverage: 212.2439
Monoisotopic: 212.083729628
Chemical FormulaC14H12O2
InChI KeySESFRYSPDFLNCH-UHFFFAOYSA-N
InChI
InChI=1S/C14H12O2/c15-14(13-9-5-2-6-10-13)16-11-12-7-3-1-4-8-12/h1-10H,11H2
IUPAC Name
benzyl benzoate
SMILES
O=C(OCC1=CC=CC=C1)C1=CC=CC=C1
Mass Specshow(8.13 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassBenzoic Acid and Derivatives
Direct parentBenzoic Acid Esters
Alternative parentsBenzyloxycarbonyls; Benzylethers; Benzoyl Derivatives; Carboxylic Acid Esters; Dialkyl Ethers; Enolates; Polyamines
Substituentsbenzoyl; carboxylic acid ester; dialkyl ether; ether; polyamine; carboxylic acid derivative; enolate
Classification descriptionThis compound belongs to the benzoic acid esters. These are ester derivatives of benzoic acid.
Pharmacology
IndicationUsed to kill lice and the mites responsible for the skin condition scabies.
PharmacodynamicsBenzyl benzoate is one of the older preparations used to treat scabies. Scabies is a skin infection caused by the mite sarcoptes scabiei. It is characterised by severe itching (particularly at night), red spots, and may lead to a secondary infection. Benzyl benzoate is lethal to this mite and so is useful in the treatment of scabies. It is also used to treat lice infestation of the head and body. Benzyl benzoate is not the treatment of choice for scabies due to its irritant properties.
Mechanism of actionBenzyl benzoate exerts toxic effects on the nervous system of the parasite, resulting in its death. It is also toxic to mite ova, though its exact mechanism of action is unknown. In vitro, benzyl benzoate has been found to kill the Sarcoptes mite within 5 minutes.
AbsorptionNo data are available on percutaneous absorption of benzyl benzoate. Some older studies have suggested some percutaneous absorption, however the amount was not quantified.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Rapidly hydrolyzed to benzoic acid and benzyl alcohol, which is further oxidized to benzoic acid. The benzoic acid is conjugated with glycine to form hippuric acid.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral, rabbit: LD50 = 1680 mg/kg; Skin, rabbit: LD50 = 4000 mg/kg. Symptoms of overdose include blister formation, crusting, itching, oozing, reddening, or scaling of skin; difficulty in urinating (dribbling); jerking movements; sudden loss of consciousness.
Affected organisms
  • Sarcoptes scabiei
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption Not Available Not Available
Blood Brain Barrier Not Available Not Available
Caco-2 permeable Not Available Not Available
P-glycoprotein substrate Not Available Not Available
P-glycoprotein inhibitor I Not Available Not Available
P-glycoprotein inhibitor II Not Available Not Available
Renal organic cation transporter Not Available Not Available
CYP450 2C9 substrate Not Available Not Available
CYP450 2D6 substrate Not Available Not Available
CYP450 3A4 substrate Not Available Not Available
CYP450 1A2 substrate Not Available Not Available
CYP450 2C9 substrate Not Available Not Available
CYP450 2D6 substrate Not Available Not Available
CYP450 2C19 substrate Not Available Not Available
CYP450 3A4 substrate Not Available Not Available
CYP450 inhibitory promiscuity Not Available Not Available
Ames test Not Available Not Available
Carcinogenicity Not Available Not Available
Biodegradation Not Available Not Available
Rat acute toxicity Not Available Not applicable
hERG inhibition (predictor I) Not Available Not Available
hERG inhibition (predictor II) Not Available Not Available
Pharmacoeconomics
Manufacturers
  • Lannett co inc
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Benzyl benzoate0.16USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Stateliquid
Experimental Properties
PropertyValueSource
melting point21 °CPhysProp
boiling point323.5 °CPhysProp
water solubility15.4 mg/LNot Available
logP3.97HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility1.98e-02 g/lALOGPS
logP3.43ALOGPS
logP3.7ChemAxon
logS-4ALOGPS
pKa (strongest basic)-6.9ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count0ChemAxon
polar surface area26.3ChemAxon
rotatable bond count4ChemAxon
refractivity62.7ChemAxon
polarizability22.85ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Henri Sidi, William G. Hughes, “Process for the production of benzoic acid from process residues that contain benzyl benzoate.” U.S. Patent US4281178, issued September, 1941.

US4281178
General Reference
  1. Bachewar NP, Thawani VR, Mali SN, Gharpure KJ, Shingade VP, Dakhale GN: Comparison of safety, efficacy, and cost effectiveness of benzyl benzoate, permethrin, and ivermectin in patients of scabies. Indian J Pharmacol. 2009 Feb;41(1):9-14. Pubmed
  2. Buffet M, Dupin N: Current treatments for scabies. Fundam Clin Pharmacol. 2003 Apr;17(2):217-25. Pubmed
External Links
ResourceLink
KEGG DrugD01138
KEGG CompoundC12537
PubChem Compound2345
PubChem Substance46508023
ChemSpider13856959
PharmGKBPA164748881
HETBZM
Drugs.comhttp://www.drugs.com/cons/benzyl-benzoate-topical.html
WikipediaBenzyl_Benzoate
ATC CodesP03AX01
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSshow(73.2 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11