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
Structure for Benzyl benzoate (DB00676)
- 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
Pharmacology
- Indication
Used to kill lice and the mites responsible for the skin condition scabies.
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- Contraindications & Blackbox Warnings
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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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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
- Not Available
Interactions
- Drug Interactions
- 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- 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
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image BENZYL BENZOATE APPLICATION BP 25% w/v Emulsion 25 % w/v Topical ICM PHARMA PTE. LTD. 1991-12-13 Not applicable Singapore RIDPED LOTION Lotion Topical WINWA MEDICAL SDN. BHD. 2020-09-08 Not applicable Malaysia 
Scabitone Emulsion Emulsion Topical SM PHARMACEUTICALS SDN. BHD. 2020-09-08 Not applicable Malaysia - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ANUCARE SUPPOSITORY Benzyl benzoate (33 mg) + Balsam of Peru (50 mg) + Zinc oxide (300 mg) Suppository Rectal Y.S.P. INDUSTRIES (M) SDN BHD 2020-09-08 Not applicable Malaysia HEMOSOL OINTMENT Benzyl benzoate (1.25 % w/w) + Balsam of Peru (1.88 % w/w) + Zinc oxide (10.75 % w/w) Ointment Topical PRIME PHARMACEUTICAL SDN. BHD. 2020-09-08 Not applicable Malaysia Hemosol suppositories Benzyl benzoate (33 mg) + Balsam of Peru (50 mg) + Zinc oxide (300 mg) Suppository Rectal PRIME PHARMACEUTICAL SDN. BHD. 2020-09-08 Not applicable Malaysia
Categories
- ATC Codes
- P03AX01 — Benzyl benzoate
- Drug Categories
- Acaricides
- Acids, Carbocyclic
- Agrochemicals
- Antiparasitic Products, Insecticides and Repellents
- Benzene Derivatives
- Compounds used in a research, industrial, or household setting
- Ectoparasiticides, Incl. Scabicides
- Ectoparasiticides, Incl. Scabicides, Insecticides and Repellents
- Insecticides
- Pesticides
- Toxic Actions
- 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
- 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]
- Buffet M, Dupin N: Current treatments for scabies. Fundam Clin Pharmacol. 2003 Apr;17(2):217-25. [Article]
- External Links
- Human Metabolome Database
- HMDB0014814
- KEGG Drug
- D01138
- KEGG Compound
- C12537
- PubChem Compound
- 2345
- PubChem Substance
- 46508023
- ChemSpider
- 13856959
- BindingDB
- 50134035
- 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
- Download (73.2 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Households / Scabies 1 2, 3 Completed Treatment Gallbladder Inflammation / Pain, Chronic / Postoperative pain / Quality of Life (QOL) 1
Pharmacoeconomics
- Manufacturers
- Lannett co inc
- Packagers
- J T Baker
- Dosage Forms
Form Route Strength Cream Cutaneous Suppository Rectal Lotion Topical 200 ml Lotion Topical 10 g Ointment Suspension Topical 25 g Lotion Topical 30 g Solution Topical 30 mL Lotion Topical 25 g Lotion Topical 25 mL Emulsion Topical 200 ml Emulsion Topical 25 % w/v Ointment Topical Lotion Topical Liquid Topical 250 mg/125ml Emulsion Topical - Prices
Unit description Cost Unit Benzyl benzoate 0.16USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) 21 °C PhysProp boiling point (°C) 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 0.0198 mg/mL 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 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 62.7 m3·mol-1 Chemaxon Polarizability 22.85 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Download (8.13 KB)
- Spectra
Drug created at June 13, 2005 13:24 / Updated at March 03, 2023 17:37