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

Molecular Formula	C14H12O2
Molecular Weight	212.2439
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Gland cell cultures into 3D hyaluronan-based scaffolds.	2003 Aug	15348416
Erythema annulare centrifugum induced by generalized Phthirus pubis infestation.	2003 Dec	14674913
Freeze-drying polymeric colloidal suspensions: nanocapsules, nanospheres and nanodispersion. A comparative study.	2003 Nov	14602195
The efficacy of benzyl benzoate sprays in killing the storage mite Tyrophagus putrescentiae (Acari: Acaridae).	2004	15236508
Controlling scabies in institutional settings: a review of medications, treatment models, and implementation.	2004	14979741
3 dimensional modelling of early human brain development using optical projection tomography.	2004 Aug 6	15298700
In vitro and in vivo antimalarial activity of peptidomimetic protein farnesyltransferase inhibitors with improved membrane permeability.	2004 Dec 15	15556768
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
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
Phytochemistry and preliminary biological evaluation of Cyathostemma argenteum, a malaysian plant used traditionally for the treatment of breast cancer.	2004 Jul	15305306
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
Controlled release of a model protein lysozyme from phase sensitive smart polymer systems.	2004 Mar 1	15129985
Synthesis of [323]-p-octiphenyls: orthogonal functionalization along a rigid-rod scaffold for refined supramolecular architecture.	2004 Mar 18	15012056
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 Melaleuca alternifolia (tea tree) oil: in vitro sensitivity of sarcoptes scabiei var hominis to terpinen-4-ol.	2004 May	15148100
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
The transmediastinal arteries of the human testis: an anatomical study.	2004 Oct	15205918
Cytocompatibility and viscoelastic properties of phthalate ester-free tissue conditioners.	2004 Sep	15510874
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
In vitro release of levonorgestrel from phase sensitive and thermosensitive smart polymer delivery systems.	2005	15926681
Floral scent emission and pollinator attraction in two species of Gymnadenia (Orchidaceae).	2005 Feb	15586296
Immunobiological [correction of Immunobioloical] activity of a new benzyl benzoate from the aerial parts of Solidago virga-aurea var. gigantea.	2005 Jan	15742808
Structure formation in injectable poly(lactide-co-glycolide) depots. II. Nature of the gel.	2005 Jan 15	15514938
Oligonucleotides conjugated to short lysine chains.	2005 Jul-Aug	16029048
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
Acaricidal activity of active constituent isolated in Chamaecyparis obtusa leaves against Dermatophagoides spp.	2005 Mar 23	15769116
Controlled delivery of testosterone from smart polymer solution based systems: in vitro evaluation.	2005 May 13	15848003
Anti-cancer ProTides: tuning the activity of BVDU phosphoramidates related to thymectacin.	2005 May 2	15809157
In vitro release of insulin and biocompatibility of in situ forming gel systems.	2005 Nov 4	16181752
Deazapurine solid-phase synthesis: combinatorial synthesis of a library of N3,N5,C6-trisubstituted pyrrolo[3,2-d]pyrimidine derivatives on cross-linked polystyrene bearing a cysteamine linker.	2005 Nov-Dec	16283810
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
Structure-activity studies of 3'-4'-dichloro-meperidine analogues at dopamine and serotonin transporters.	2005 Oct 1	15993612
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
Chemical-physical characterization and in vitro preliminary biological assessment of hyaluronic acid benzyl ester-hydroxyapatite composite.	2006 Jan	16364964
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)

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:13:30 GMT 2023` Edited by `admin` on `Fri Dec 15 15:13:30 GMT 2023`
Record UNII	N863NB338G
Record Status	`Validated (UNII)`
Record Version

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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