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
New microencapsulated sunscreens: technology and comparative evaluation.	2002 Aug 21	12176248
[Determination of volatile constituents in guanxin suhe wan by gas chromatography-mass spectrometry].	2002 Jul	12541931
Benzoate X receptors alpha and beta are pharmacologically distinct and do not function as xenobiotic receptors.	2002 Nov 15	12198127
[Stereochemistry of the reductive amination of 4-oxoproline derivatives with glycine esters].	2002 Nov-Dec	12528461
Bullous hematoma of the palm: an unusual complication of scabies in a child with congenital prothrombin deficiency.	2002 Nov-Dec	12437569
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
Acaricidal activity of Uvaria versicolor and Uvaria Klaineana (Annonaceae).	2003 Apr	12722141
Gland cell cultures into 3D hyaluronan-based scaffolds.	2003 Aug	15348416
Acaricidal activity of clove bud oil compounds against Dermatophagoides farinae and Dermatophagoides pteronyssinus (Acari: Pyroglyphidae).	2003 Feb 12	12568544
Understanding scabies.	2003 Feb 18-24	12655753
Acaricidal activity of Cnidium officinale rhizome-derived butylidenephthalide against Tyrophagus putrescentiae (Acari: Acaridae).	2003 Jan	12558107
Atovaquone-loaded nanocapsules: influence of the nature of the polymer on their in vitro characteristics.	2003 Jan 2	12480292
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
Molecular markers of anthropogenic activity in sediments of the Havel and Spree Rivers (Germany).	2003 Jun	12753838
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
Quantitative fluorescence of 5-FU-treated fetal rat limbs using confocal laser scanning microscopy and Lysotracker Red.	2003 May	12701128
Potential cncer chemopreventive flavonoids from the stems of Tephrosia toxicaria.	2003 Sep	14510590
The efficacy of benzyl benzoate sprays in killing the storage mite Tyrophagus putrescentiae (Acari: Acaridae).	2004	15236508
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
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
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: epidemiology; assessment of clinical, haematological, cell-mediated humoral immune responses and pathology.	2004 Mar	15153076
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
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
Cytocompatibility and viscoelastic properties of phthalate ester-free tissue conditioners.	2004 Sep	15510874
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
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
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
Structure-activity studies of 3'-4'-dichloro-meperidine analogues at dopamine and serotonin transporters.	2005 Oct 1	15993612
Free radical generation during chemical depolymerization of heparin.	2005 Sep 15	16098471

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