Benzyl benzoate

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H12O2
Molecular Weight	212.2439
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C(OCC1=CC=CC=C1)C2=CC=CC=C2

InChI

InChIKey=SESFRYSPDFLNCH-UHFFFAOYSA-N

InChI=1S/C14H12O2/c15-14(13-9-5-2-6-10-13)16-11-12-7-3-1-4-8-12/h1-10H,11H2

HIDE SMILES / InChI

Description
Sources: http://apps.who.int/medicinedocs/en/d/Jh2918e/27.html#Jh2918e.27.1
Curator's Comment: description was created based on several sources, including: https://en.wikipedia.org/wiki/Benzyl_benzoate http://www.drugbank.ca/drugs/DB00676

Benzyl benzoate is an organic compound with the formula C6H5CH2O2CC6H5. It is the ester of benzyl alcohol and benzoic acid. It forms either a viscous liquid or solid flakes and has a weak, sweet-balsamic odor. It occurs in a number of blossoms (e. g. tuberose, hyacinth) and is a component of Balsam of Peru and Tolu balsam. It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system. 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. 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.

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Sunburn 84 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f4a264f7-95c5-4d6c-aaa7-f3749719cf96	Inactive ingredient	Approved 8429	BRIGHTENING DYNAMICS TRAVELING KIT JAFRA Approved Use Helps prevent sunnburn. If used as directed, with other sun protection measures (see directions), decreases the risk of skin cancer and early skin aging caused by the sun.
Pediculosis caused by Pediculus capitis (head louse) and Phthirus pubis (pubic or crab louse) 1 Sources: http://www.drugs.com/cons/benzyl-benzoate-topical.html	Curative	Withdrawn	BENZYL BENZOATE Approved Use Unknown Launch Date 1976
Scabies caused by the Sarcoptes scabiei mite. 1 Sources: http://www.drugs.com/cons/benzyl-benzoate-topical.html	Curative	Withdrawn	BENZYL BENZOATE Approved Use Unknown Launch Date 1976

Doses

Dose	Population	Adverse events
10 % 1 times / day multiple, topical Dose: 10 %, 1 times / day Route: topical Route: multiple Dose: 10 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12174005	unhealthy, 4.7 years (range: 6 months - 15 years) n = 37 Health Status: unhealthy Condition: Scabies Age Group: 4.7 years (range: 6 months - 15 years) Population Size: 37 Sources: https://pubmed.ncbi.nlm.nih.gov/12174005	Other AEs: Localised skin reaction... Other AEs: Localised skin reaction (12 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/12174005
25 % 1 times / day multiple, topical Dose: 25 %, 1 times / day Route: topical Route: multiple Dose: 25 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17439567	pregnant, adult n = 444 Health Status: pregnant Condition: scabies Age Group: adult Sex: F Population Size: 444 Sources: https://pubmed.ncbi.nlm.nih.gov/17439567	Sources: https://pubmed.ncbi.nlm.nih.gov/17439567

AEs

AE	Significance	Dose	Population
Localised skin reaction	12 patients	10 % 1 times / day multiple, topical Dose: 10 %, 1 times / day Route: topical Route: multiple Dose: 10 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12174005	unhealthy, 4.7 years (range: 6 months - 15 years) n = 37 Health Status: unhealthy Condition: Scabies Age Group: 4.7 years (range: 6 months - 15 years) Population Size: 37 Sources: https://pubmed.ncbi.nlm.nih.gov/12174005

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:41237	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:41237
ChemicalBook	CB9152283	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9152283
MolPort	MolPort-001-740-297	https://www.molport.com/shop/molecule-link/MolPort-001-740-297
ZINC	ZINC000000001021	http://zinc15.docking.org/substances/ZINC000000001021
eMolecules	479707	https://www.emolecules.com/cgi-bin/more?vid=479707

PubMed

Title	Date	PubMed
Antineoplastic agents 460. Synthesis of combretastatin A-2 prodrugs.	2001 Aug-Oct	12049477
The use of ELM to monitor the success of antiscabietic treatment. Epiluminescence light microscopy.	2001 Dec	11735726
Scabies presenting as a blistering eruption.	2001 Oct	11710447
Klaivanolide, an antiprotozoal lactone from Uvaria klaineana.	2002 Apr	11937171
[Determination of volatile constituents in guanxin suhe wan by gas chromatography-mass spectrometry].	2002 Jul	12541931
Comparison of the antioxidant properties of HYAFF-11p75, AQUACEL and hyaluronan towards reactive oxygen species in vitro.	2002 May	11962667
Diagnosis and treatment of scabies in 2002: rapid diagnosis and proper management limit the risk of spread.	2002 Oct	12378748
Characterization of an acyltransferase capable of synthesizing benzylbenzoate and other volatile esters in flowers and damaged leaves of Clarkia breweri.	2002 Sep	12226525
Current treatments for scabies.	2003 Apr	12667233
Gland cell cultures into 3D hyaluronan-based scaffolds.	2003 Aug	15348416
Optimization of polylactic-co-glycolic acid nanoparticles containing itraconazole using 2(3) factorial design.	2003 Dec 31	15198566
Understanding scabies.	2003 Feb 18-24	12655753
Atovaquone-loaded nanocapsules: influence of the nature of the polymer on their in vitro characteristics.	2003 Jan 2	12480292
Structure formation in injectable poly(lactide-co-glycolide) depots.	2003 Jul 31	12880701
Autologous human keratinocytes cultured on membranes composed of benzyl ester of hyaluronic acid for grafting in nonhealing diabetic foot lesions: a pilot study.	2003 Jul-Aug	12810243
Estrogenic activity of tissue conditioners in vitro.	2003 Jun	12686300
Pd/C-catalyzed chemoselective hydrogenation in the presence of a phenolic MPM protective group using pyridine as a catalyst poison.	2003 Mar	12612421
Acaricidal activity of tonka bean extracts. Synthesis and structure-activity relationships of bioactive derivatives.	2003 May	12762809
A trial to assess the efficacy and tolerability of Hyalofill-F in non-healing venous leg ulcers.	2003 Oct	14601230
Identification and prediction of promiscuous aggregating inhibitors among known drugs.	2003 Oct 9	14521410
Cost-benefit analysis of ivermectin, permethrin and benzyl benzoate in the management of infantile and childhood scabies.	2003 Sep	12943481
The efficacy of benzyl benzoate sprays in killing the storage mite Tyrophagus putrescentiae (Acari: Acaridae).	2004	15236508
Design, synthesis, and photochemical behavior of poly(benzyl ester) dendrimers with azobenzene groups throughout their architecture.	2004 Dec 24	15609940
Acaricidal activity of Paeonia suffruticosa root bark-derived compounds against Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae).	2004 Dec 29	15612767
Leaching of plasticizers from temporary denture soft lining materials.	2004 Feb	14871201
Isotropic medium chain mono-diglyceride/oil/water formulations for solubilization of lipophilic and hydrophilic drugs.	2004 Feb 11	14726143
Inhibition of alpha-chymotrypsin with thiol-bearing substrate analogues in the presence of zinc ion.	2004 Feb 9	14741272
[Reconstruction of extensive soft tissue loss by transplantation of dermal and epidermal equivalents].	2004 Jan	15011109
Synthesis and characterization of branched poly(L-glutamic acid) as a biodegradable drug carrier.	2004 Jan 8	14684270
[Nosocomial infection of scabies in national hospitals and sanatoria in Japan].	2004 Jul	15387285
Effects of sarcoptic mange and its control with oil of Cedrus deodara, Pongamia glabra, Jatropha curcas and benzyl benzoate, both with and without ascorbic acid on growing sheep: assessment of weight gain, liver function, nutrient digestibility, wool production and meat quality.	2004 Mar	15153077
p-Anisaldehyde: acaricidal component of Pimpinella anisum seed oil against the house dust mites Dermatophagoides farinae and Dermatophagoides pteronyssinus.	2004 Mar	15114512
Genetic and molecular basis of grass cell-wall degradability. I. Lignin-cell wall matrix interactions.	2004 May	15255476
An evaluation of Hyalofill-F plus compression bandaging in the treatment of chronic venous ulcers.	2004 May	15160576
Acaricidal activity of constituents identified in Foeniculum vulgare fruit oil against Dermatophagoides spp. (Acari: Pyroglyphidae).	2004 May 19	15137830
Rapid and sensitive quantitative analysis of alkyl phosphates in urine after organophosphate poisoning.	2004 May-Jun	15189674
Block copolymer design for camptothecin incorporation into polymeric micelles for passive tumor targeting.	2004 Nov	15587921
Drug release from injectable depots: two different in vitro mechanisms.	2004 Sep 30	15380631
Efficacy of various synthetic pyrethroid-impregnated encasement materials against house dust mite under laboratory conditions.	2005	15969462
Floral scent emission and pollinator attraction in two species of Gymnadenia (Orchidaceae).	2005 Feb	15586296
Food protective effect of acaricidal components isolated from anise seeds against the stored food mite, Tyrophagus putrescentiae (Schrank).	2005 Jun	15954709
SAR studies of brasilicardin A for immunosuppressive and cytotoxic activities.	2005 Mar 1	15698766
In vitro release of insulin and biocompatibility of in situ forming gel systems.	2005 Nov 4	16181752
Effect of co-solvents on the controlled release of calcitonin polypeptide from in situ biodegradable polymer implants.	2005 Nov-Dec	16253955
Design of wide-spectrum inhibitors targeting coronavirus main proteases.	2005 Oct	16128623
Pthiriasis capitis.	2005 Sep	16135150
Free radical generation during chemical depolymerization of heparin.	2005 Sep 15	16098471
Crusted scabies in an adult T-cell leukemia/lymphoma patient successfully treated with oral ivermectin.	2006 Feb	16556285
Aluminum sulfate significantly reduces the skin test response to common allergens in sensitized patients.	2006 Feb 14	16478539
Acaricidal activities of paeonol and benzoic acid from Paeonia suffruticosa root bark and monoterpenoids against Tyrophagus putrescentiae (Acari: Acaridae).	2006 Jun	16602084

Patents

Sample Use Guides

In Vivo Use Guide

30 mL of the lotion usually is sufficient for one application in adults and 20 mL usually is sufficient in children. The patient should bathe 24–48 hours after the last application to remove the drug.

Route of Administration: Topical

In Vitro Use Guide

no mites were alive after 3 h exposure to 25% benzyl benzoate (Ascabiol)

Name

Type

Language

Benzyl benzoate

Official Name

English

SCABIOZON

Common Name

English

BENZYL BENZOATE [EP IMPURITY]

Common Name

English

BENZYL BENZOATE [MART.]

Common Name

English

BENZYL BENZOATE [USP-RS]

Common Name

English

BENZYL BENZOATE [USP MONOGRAPH]

Common Name

English

BENZOIC ACID, BENZYL ESTER

Common Name

English

Benzyl benzoate [WHO-DD]

Common Name

English

BENZYLIS BENZOAS [WHO-IP LATIN]

Common Name

English

NSC-8081

Code

English

BENZYL BENZOATE [II]

Common Name

English

VENZONATE

Common Name

English

BENZYL BENZOATE [ORANGE BOOK]

Common Name

English

BENZYLOXY PHENYL KETONE

Systematic Name

English

BENZYL BENZOATE [HSDB]

Common Name

English

PHENYLMETHYL BENZOATE

Systematic Name

English

BENZYL BENZOATE [INCI]

Common Name

English

BENZYL BENZOATE [USP IMPURITY]

Common Name

English

BENZYL BENZOATE [MI]

Common Name

English

BENZYL BENZOATE [FHFI]

Common Name

English

BENZYL BENZOATE [EP MONOGRAPH]

Common Name

English

BENZYL BENZOATE [FCC]

Common Name

English

BENZYL BENZOATE [WHO-IP]

Common Name

English

BENZYLBENZENECARBOXYLATE

Systematic Name

English

BENZYL BENZOATE [JAN]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 172.515