Benzyl Benzoate

Identification

Name
Benzyl Benzoate
Accession Number
DB00676  (APRD00821, EXPT00792, DB02775)
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.

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
External IDs
FEMA NO. 2138 / NSC-8081
International/Other Brands
Acaril-S (Medifarma) / Acarilbial (Bial) / Acarsan (Biosintética) / Acil (Didy Pharmaceutical) / Antiscabiosum (Strathmann) / Antiscabiosum für Kinder (Strathmann) / Ascabiol (Sanofi-Aventis) / Ascalol (Pharmaghreb) / B.B. Lotion (Washington) / BE BO (Aesculap) / Benzalcor (Corsalud) / Benzilbenzoat (Labor) / Benzogal (Rafarm) / Benzotal (Grindeks) / Bezo (Medisearch) / Finsarna (Qualicont) / Gensarna (Gencopharmaceutical) / Miticocan (Aché) / Novoscabin (Polon) / Opele (Beta Health Care) / Pharcobenzyl (Pharco) / Sanasar (Kley Hertz) / Saniscabis (Neo-Fármaco) / Scabicon (Medicon) / Scabiex (Rekah) / Scabin (Abdi Ibrahim) / Scabisol (Jayson) / Scabitox (Bosnalijek) / Spasmodine / Tekoce (Jadran) / Zilaben (Cristália)
Categories
UNII
N863NB338G
CAS number
120-51-4
Weight
Average: 212.2439
Monoisotopic: 212.083729628
Chemical Formula
C14H12O2
InChI Key
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

Pharmacology

Indication

Used to kill lice and the mites responsible for the skin condition scabies.

Structured Indications
Not Available
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 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
Human Metabolome Database
HMDB14814
KEGG Drug
D01138
KEGG Compound
C12537
PubChem Compound
2345
PubChem Substance
46508023
ChemSpider
13856959
BindingDB
50134035
ChEBI
41237
ChEMBL
CHEMBL1239
PharmGKB
PA164748881
HET
BZM
Drugs.com
Drugs.com Drug Page
Wikipedia
Benzyl_Benzoate
ATC Codes
P03AX01 — Benzyl benzoate
AHFS Codes
Not Available
PDB Entries
1dzm
FDA label
Not Available
MSDS
Download (73.2 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Lannett co inc
Packagers
Dosage forms
Not Available
Prices
Unit descriptionCostUnit
Benzyl benzoate0.16USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)21 °CPhysProp
boiling point (°C)323.5 °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 RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Download (8.13 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-9600000000-053d8df1e84bfa72c807
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-7920000000-b0cd2b3fa8283d974d76
GC-MS Spectrum - EI-BGC-MSsplash10-0a4l-9810000000-7d82df2148f364364d37
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-9810000000-e3b80444bd7ae9437590
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-3930000000-fa4d81201ce0caa8539c
GC-MS Spectrum - CI-BGC-MSsplash10-0a4i-5910000000-c5210f9077b94a2f81e1
GC-MS Spectrum - EI-BGC-MSsplash10-056r-9300000000-b15752c1190b0242b115
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-7920000000-e4f7251f775b85f6af09
GC-MS Spectrum - EI-BGC-MSsplash10-0a4l-9610000000-37d8d16fbb06548d4614
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-4920000000-a552e18b70960ed092be
GC-MS Spectrum - EI-BGC-MSsplash10-0a4i-9720000000-f05c57dce7b414894a2e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dl-5490000000-15fa8c981873e04a4104
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9410000000-dd2fad4669879cae9bab
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-9400000000-ed36c8093ac8fb2fcec9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1290000000-9376f66197b6ec97a065
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0hb9-5940000000-0cd238ce8d207b3f089f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9500000000-3b482d60ff1be3b17be1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dl-5490000000-15fa8c981873e04a4104
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9410000000-dd2fad4669879cae9bab
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-9400000000-ed36c8093ac8fb2fcec9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1290000000-9376f66197b6ec97a065
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0hb9-5940000000-0cd238ce8d207b3f089f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9500000000-3b482d60ff1be3b17be1

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Benzoic acid esters
Alternative Parents
Benzyloxycarbonyls / Benzoyl derivatives / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Benzyloxycarbonyl / Benzoate ester / Benzoyl / Carboxylic acid ester / Monocarboxylic acid or derivatives / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative / Organooxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
benzoate ester (CHEBI:41237) / a small molecule (CPD-6443)

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:42