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Identification
Name Benzyl Benzoate
Accession Number DB00676 (APRD00821)
Type small molecule
Groups approved
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.
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Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Ascabin
Ascabiol
Benylate
Benzoic acid benzyl ester
Benzoic acid, benzyl ester
Benzoic acid, phenylmethyl ester
Benzyl alcohol benzoic ester
Benzyl benzenecarboxylate
Benzyl benzoate 99+ %
Benzyl ester
Benzyl phenylformate
Benzylester kyseliny benzoove
Benzylets
Colebenz
Novoscabin
Peruscabin
Scabagen
Scabanca
Scabide
Scabiozon
Scabitox
Scobenol
Vanzoate
Venzoate
Venzonate
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Brand mixtures
Brand Name Ingredients
Dermadex Crm Benzoic Acid + Benzyl Benzoate + Lindane + Salicylic Acid + Zinc Oxide + Zinc Undecylenate
Categories
  • Insecticides
  • Acaricides
CAS number 120-51-4
Weight Average: 212.2439
Monoisotopic: 212.083729628
Chemical Formula C14H12O2
InChI Key InChIKey=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
Plain Text
IUPAC Name
benzyl benzoate
SMILES
O=C(OCC1=CC=CC=C1)C1=CC=CC=C1
Plain Text
Mass Spec show (8.13 KB)
Taxonomy
Kingdom Organic
Classes
  • Aminobenzoates
  • Benzene and Derivatives
  • Benzyl Esters
  • Benzylacetates
Substructures
  • Aminobenzoates
  • Carboxylic Acids and Derivatives
  • Benzyl Alcohols and Derivatives
  • Acetates
  • Benzoates
  • Ethers
  • Benzene and Derivatives
  • Benzyl Esters
  • Benzylacetates
  • Aromatic compounds
  • Benzoyl Derivatives
Pharmacology
Indication Used to kill lice and the mites responsible for the skin condition scabies.
Pharmacodynamics 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.
Mechanism of action Benzyl 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.
Absorption No 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 distribution Not Available
Protein binding Not 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 elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Oral, 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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Lannett co inc
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
Benzyl benzoate 0.16 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State liquid
Experimental Properties
Property Value Source
melting point 21 °C PhysProp
boiling point 323.5 °C PhysProp
water solubility 15.4 mg/L Not Available
logP 3.97 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
water solubility 1.98e-02 g/l ALOGPS
logP 3.43 ALOGPS
logP 3.7 ChemAxon
logS -4 ALOGPS
pKa (strongest basic) -6.9 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 26.3 ChemAxon
rotatable bond count 4 ChemAxon
refractivity 62.7 ChemAxon
polarizability 22.85 ChemAxon
References
Synthesis Reference Not Available
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
Resource Link
KEGG Drug D01138 Link_out
PubChem Compound 2345 Link_out
PubChem Substance 46508023 Link_out
ChemSpider 13856959 Link_out
PharmGKB PA164748881 Link_out
Drugs.com http://www.drugs.com/cons/benzyl-benzoate-topical.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Benzyl_Benzoate Link_out
ATC Codes
  • P03AX01
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (73.2 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19