NAV

Benzyl benzoate

Identification

Summary

Benzyl benzoate is a topical treatment for scabies and lice.

Generic Name
Benzyl benzoate
DrugBank Accession Number
DB00676
Background

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.

Type
Small Molecule
Groups
Approved
Structure
3D
Similar Structures
Weight
Average: 212.2439
Monoisotopic: 212.083729628
Chemical Formula
C14H12O2
Synonyms
  • Acarobenzyl
  • Benylate
  • Benzevan
  • Benzoate de benzyle
  • Benzoesäurebenzylester
  • Benzoic acid phenylmethylester
  • Benzoic acid, benzyl ester
  • Benzoic acid, phenylmethyl ester
  • Benzyl benzoat
  • Benzyl benzoate
  • Benzylis benzoas
  • Phenylmethyl benzoate
External IDs
  • FEMA NO. 2138
  • NSC-8081
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Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofLice••••••••••••••••••••• ••••••• ••••••• ••••••••• ••••••••••
Treatment ofScabies••••••••••••••••••••• ••••••• ••••••• ••••••••• ••••••••••
Contraindications & Blackbox Warnings
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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

Adverse Effects
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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.

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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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) / Tekoce (Jadran) / Zilaben (Cristália)
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BENZYL BENZOATE APPLICATION BP 25% w/vEmulsion25 % w/vTopicalICM PHARMA PTE. LTD.1991-12-13Not applicableSingapore flag
RIDPED LOTIONLotionTopicalWINWA MEDICAL SDN. BHD.2020-09-08Not applicableMalaysia flag
Scabitone EmulsionEmulsionTopicalSM PHARMACEUTICALS SDN. BHD.2020-09-08Not applicableMalaysia flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ANUCARE SUPPOSITORYBenzyl benzoate (33 mg) + Balsam of Peru (50 mg) + Zinc oxide (300 mg)SuppositoryRectalY.S.P. INDUSTRIES (M) SDN BHD2020-09-08Not applicableMalaysia flag
HEMOSOL OINTMENTBenzyl benzoate (1.25 % w/w) + Balsam of Peru (1.88 % w/w) + Zinc oxide (10.75 % w/w)OintmentTopicalPRIME PHARMACEUTICAL SDN. BHD.2020-09-08Not applicableMalaysia flag
Hemosol suppositoriesBenzyl benzoate (33 mg) + Balsam of Peru (50 mg) + Zinc oxide (300 mg)SuppositoryRectalPRIME PHARMACEUTICAL SDN. BHD.2020-09-08Not applicableMalaysia flag

Categories

ATC Codes
P03AX01 — Benzyl benzoate
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aromatic homomonocyclic compound / Benzoate ester / Benzoyl / Benzyloxycarbonyl / Carboxylic acid derivative / Carboxylic acid ester / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
benzoate ester (CHEBI:41237) / a small molecule (CPD-6443)
Affected organisms
  • Sarcoptes scabiei

Chemical Identifiers

UNII
N863NB338G
CAS number
120-51-4
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

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. [Article]
  2. Buffet M, Dupin N: Current treatments for scabies. Fundam Clin Pharmacol. 2003 Apr;17(2):217-25. [Article]
Human Metabolome Database
HMDB0014814
KEGG Drug
D01138
KEGG Compound
C12537
PubChem Compound
2345
PubChem Substance
46508023
ChemSpider
13856959
BindingDB
50134035
RxNav
19044
ChEBI
41237
ChEMBL
CHEMBL1239
ZINC
ZINC000000001021
PharmGKB
PA164748881
PDBe Ligand
BZM
Drugs.com
Drugs.com Drug Page
Wikipedia
Benzyl_benzoate
PDB Entries
1dzm / 5nna
MSDS
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Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4CompletedTreatmentHouseholds / Scabies1
2, 3CompletedTreatmentChronic Pain / Gallbladder Inflammation / Postoperative pain / Quality of Life (QOL)1

Pharmacoeconomics

Manufacturers
  • Lannett co inc
Packagers
  • J T Baker
Dosage Forms
FormRouteStrength
CreamCutaneous
SuppositoryRectal
LotionTopical200 ml
LotionTopical10 g
Ointment
SuspensionTopical25 g
LotionTopical30 g
SolutionTopical30 mL
SolutionTopical3000000 mL
LotionTopical25 mL
LotionTopical25 g
EmulsionTopical200 ml
EmulsionTopical25 % w/v
OintmentTopical
LotionTopical
LiquidTopical250 mg/125ml
EmulsionTopical
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)
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Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9000000000-5f1ad29b0d2e8f8a42c7
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/MSsplash10-052f-9600000000-bbf30f47fe65a67e6562
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0940000000-9d4ca6b80b8ab1f08676
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-da0bbb90e907a6830cee
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9300000000-7f74e2d904d75cd9b569
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ktf-9200000000-9236b56c34db0701da6a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a6r-6910000000-6ef8f153e201175c59a7
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-151.3170633
predicted
DarkChem Lite v0.1.0
[M-H]-151.6100633
predicted
DarkChem Lite v0.1.0
[M-H]-151.4952633
predicted
DarkChem Lite v0.1.0
[M-H]-151.5200633
predicted
DarkChem Lite v0.1.0
[M-H]-142.98035
predicted
DeepCCS 1.0 (2019)
[M+H]+150.9251633
predicted
DarkChem Lite v0.1.0
[M+H]+151.1603633
predicted
DarkChem Lite v0.1.0
[M+H]+150.9330633
predicted
DarkChem Lite v0.1.0
[M+H]+150.6813633
predicted
DarkChem Lite v0.1.0
[M+H]+145.37593
predicted
DeepCCS 1.0 (2019)
[M+Na]+150.6506633
predicted
DarkChem Lite v0.1.0
[M+Na]+150.6889633
predicted
DarkChem Lite v0.1.0
[M+Na]+150.4572633
predicted
DarkChem Lite v0.1.0
[M+Na]+151.45337
predicted
DeepCCS 1.0 (2019)

Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:54