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Identification
NameBenzyl Benzoate
Accession NumberDB00676  (APRD00821, EXPT00792, DB02775)
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
Acarobenzyl
Benylate
Benzevan
Benzoate de benzyle
Benzoesäurebenzylester
BENZOIC acid phenylmethylester
Benzoic acid, benzyl ester
Benzoic acid, phenylmethyl ester
Benzyl benzoat
Benzylis benzoas
Phenylmethyl benzoate
Spasmodine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
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 mixturesNot Available
SaltsNot Available
Categories
UNIIN863NB338G
CAS number120-51-4
WeightAverage: 212.2439
Monoisotopic: 212.083729628
Chemical FormulaC14H12O2
InChI KeyInChIKey=SESFRYSPDFLNCH-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzyloxycarbonyl
  • Benzoate ester
  • Benzylether
  • Benzoyl
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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.
Related Articles
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
PropertyValueProbability
Human Intestinal AbsorptionNot AvailableNot Available
Blood Brain BarrierNot AvailableNot Available
Caco-2 permeableNot AvailableNot Available
P-glycoprotein substrateNot AvailableNot Available
P-glycoprotein inhibitor INot AvailableNot Available
P-glycoprotein inhibitor IINot AvailableNot Available
Renal organic cation transporterNot AvailableNot Available
CYP450 2C9 substrateNot AvailableNot Available
CYP450 2D6 substrateNot AvailableNot Available
CYP450 3A4 substrateNot AvailableNot Available
CYP450 1A2 substrateNot AvailableNot Available
CYP450 2C9 inhibitorNot AvailableNot Available
CYP450 2D6 inhibitorNot AvailableNot Available
CYP450 2C19 inhibitorNot AvailableNot Available
CYP450 3A4 inhibitorNot AvailableNot Available
CYP450 inhibitory promiscuityNot AvailableNot Available
Ames testNot AvailableNot Available
CarcinogenicityNot AvailableNot Available
BiodegradationNot AvailableNot Available
Rat acute toxicityNot AvailableNot applicable
hERG inhibition (predictor I)Not AvailableNot Available
hERG inhibition (predictor II)Not AvailableNot Available
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Lannett co inc
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Benzyl benzoate0.16USD ml
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 Solubility0.0198 mg/mLALOGPS
logP3.43ALOGPS
logP3.7ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.7 m3·mol-1ChemAxon
Polarizability22.85 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (8.13 KB)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-5490000000-15fa8c981873e04a4104View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9410000000-dd2fad4669879cae9babView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9400000000-ed36c8093ac8fb2fcec9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1290000000-9376f66197b6ec97a065View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0hb9-5940000000-0cd238ce8d207b3f089fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9500000000-3b482d60ff1be3b17be1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-5490000000-15fa8c981873e04a4104View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9410000000-dd2fad4669879cae9babView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9400000000-ed36c8093ac8fb2fcec9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1290000000-9376f66197b6ec97a065View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0hb9-5940000000-0cd238ce8d207b3f089fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9500000000-3b482d60ff1be3b17be1View in MoNA
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 References
  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. doi: 10.4103/0253-7613.48882. [PubMed:20177574 ]
  2. Buffet M, Dupin N: Current treatments for scabies. Fundam Clin Pharmacol. 2003 Apr;17(2):217-25. [PubMed:12667233 ]
External Links
ATC CodesP03AX01
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (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