U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C7H8O
Molecular Weight 108.1378
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Benzyl alcohol

SMILES

OCC1=CC=CC=C1

InChI

InChIKey=WVDDGKGOMKODPV-UHFFFAOYSA-N
InChI=1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2

HIDE SMILES / InChI

Molecular Formula C7H8O
Molecular Weight 108.1378
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including, http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/022129s005lbl.pdf

Benzyl Alcohol is an aromatic alcohol used in a wide variety of cosmetic formulations as a fragrance component, preservative, solvent, and viscosity-decreasing agent. FDA agency approved benzyl alcohol for the treatment of head lice. The drug acts on head lice by inhibiting them from closing their respiratory spiracles, allowing the vehicle to obstruct the spiracles and causing the lice to asphyxiate.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
ULESFIA

Approved Use

Topical treatment of head lice infestation in patients 6 months of age and older.

Launch Date

1.23923517E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1.8 μM
0.46 mmol single, subcutaneous
dose: 0.46 mmol
route of administration: Subcutaneous
experiment type: SINGLE
co-administered: NANDROLONE DECANOATE
BENZOIC ACID serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
34.8 μM
0.46 mmol single, subcutaneous
dose: 0.46 mmol
route of administration: Subcutaneous
experiment type: SINGLE
co-administered: NANDROLONE DECANOATE
BENZYL ALCOHOL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
16.6 μM
0.46 mmol single, subcutaneous
dose: 0.46 mmol
route of administration: Subcutaneous
experiment type: SINGLE
co-administered: NANDROLONE DECANOATE
HIPPURIC ACID serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
417.4 μM × h
0.46 mmol single, subcutaneous
dose: 0.46 mmol
route of administration: Subcutaneous
experiment type: SINGLE
co-administered: NANDROLONE DECANOATE
BENZOIC ACID serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
397.3 μM × h
0.46 mmol single, subcutaneous
dose: 0.46 mmol
route of administration: Subcutaneous
experiment type: SINGLE
co-administered: NANDROLONE DECANOATE
BENZYL ALCOHOL serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
7113.6 μM × h
0.46 mmol single, subcutaneous
dose: 0.46 mmol
route of administration: Subcutaneous
experiment type: SINGLE
co-administered: NANDROLONE DECANOATE
HIPPURIC ACID serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
234 mg/kg multiple, intravenous
Overdose
Dose: 234 mg/kg
Route: intravenous
Route: multiple
Dose: 234 mg/kg
Sources:
unhealthy, 29 weeks (range: 26-34 weeks)
n = 10
Health Status: unhealthy
Condition: gasping syndrome
Age Group: 29 weeks (range: 26-34 weeks)
Population Size: 10
Sources:
Disc. AE: Toxic reaction (NOS)...
AEs leading to
discontinuation/dose reduction:
Toxic reaction (NOS) (grade 5, 2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Toxic reaction (NOS) grade 5, 2 patients
Disc. AE
234 mg/kg multiple, intravenous
Overdose
Dose: 234 mg/kg
Route: intravenous
Route: multiple
Dose: 234 mg/kg
Sources:
unhealthy, 29 weeks (range: 26-34 weeks)
n = 10
Health Status: unhealthy
Condition: gasping syndrome
Age Group: 29 weeks (range: 26-34 weeks)
Population Size: 10
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >10000 uM]
weak [IC50 2440 uM]
weak [IC50 7020 uM]
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Effect of benzene, toluene, xylene on the semen quality and the function of accessory gonad of exposed workers.
2001 Apr
Benzyl alcohol, kernicterus, and unbound bilirubin.
2001 Aug
Synthesis, structure, and redox and catalytic properties of a new family of ruthenium complexes containing the tridentate bpea ligand.
2001 Aug 13
Synthesis, characterization, and catalysis of mixed-ligand lithium aggregates, excellent initiators for the ring-opening polymerization of L-lactide.
2001 Aug 22
B(C6F5)3-catalyzed allylation of secondary benzyl acetates with allylsilanes.
2001 Aug 23
Mechanism of cytochrome P4503A4- and 2D6-catalyzed dehydrogenation of ezlopitant as probed with isotope effects using five deuterated analogs.
2001 Dec
Assembly of a robust, thermally stable porous cobalt(II) nicotinate framework based on a dicobalt carboxylate unit.
2001 Dec 3
Dynamic structures of horse liver alcohol dehydrogenase (HLADH): results of molecular dynamics simulations of HLADH-NAD(+)-PhCH(2)OH, HLADH-NAD(+)-PhCH(2)O(-), and HLADH-NADH-PhCHO.
2001 Dec 5
Separation of basic, acidic and neutral compounds by capillary electrochromatography using uncharged monolithic capillary columns modified with anionic and cationic surfactants.
2001 Feb
The effect of air-drying on glycosidically bound volatiles from seasonally collected origano (Origanum vulgare ssp. hirtum) from Croatia.
2001 Feb
Prochiral selectivity in H(2)O(2)-promoted oxidation of arylalkanols catalysed by chloroperoxidase. The role of the interactions between the OH group and the amino-acid residues in the enzyme active site.
2001 Feb
Metabolic engineering of bacteria for environmental applications: construction of Pseudomonas strains for biodegradation of 2-chlorotoluene.
2001 Feb 13
Probes of hydrogen tunneling with horse liver alcohol dehydrogenase at subzero temperatures.
2001 Feb 20
Racemization kinetics of meluadrine tartrate in aqueous solution.
2001 Jan
Distal infantile neuroaxonal dystrophy--a new familial variant with perineuronal argyrophilic bodies.
2001 Jul
First stereoselective synthesis of (+)-magnostellin C, a tetrahydrofuran type of lignan bearing a chiral secondary benzyl alcohol.
2001 Jul
Cold-activation of Brassica napus BN115 promoter is mediated by structural changes in membranes and cytoskeleton, and requires Ca2+ influx.
2001 Jul
Three double-blind, randomized trials evaluating the safety and tolerance of different formulations of the saponin adjuvant QS-21.
2001 Jul 16
A novel PI index and its applications to QSPR/QSAR studies.
2001 Jul-Aug
Fatal hemolysis after high-dose etoposide: is benzyl alcohol to blame?
2001 Jun
Rhenium(I) carbonyl complexes of 2,4,6-tris(2-pyridyl)-1,3,5-triazine (TPT). Rhenium(I)-promoted methoxylation of the triazine ring carbon atom in dinuclear rhenium complexes.
2001 Jun 4
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
Biphasic membrane effects of capsaicin, an active component in Capsicum species.
2001 May
Synthetic studies on dendritic glycoclusters: a convergent palladium-catalyzed strategy.
2001 May 18
Model prodrugs for the intestinal oligopeptide transporter: model drug release in aqueous solution and in various biological media.
2001 May 18
Benzyl alcohol with epinephrine as an alternative to lidocaine with epinephrine.
2001 Nov
A concise total synthesis of the azaphenanthrene alkaloid eupolauramine.
2001 Nov 30
Biotransformation of benzaldehyde into (R)-phenylacetylcarbinol by filamentous fungi or their extracts.
2001 Oct
Volatiles from Ficus hispida and their attractiveness to fig wasps.
2001 Oct
Biochemical and physiological studies of the small heat shock protein Lo18 from the lactic acid bacterium Oenococcus oeni.
2001 Oct
Contact urticaria from benzyl alcohol presenting as intolerance to saline soaks.
2001 Sep
Dipeptide model prodrugs for the intestinal oligopeptide transporter. Affinity for and transport via hPepT1 in the human intestinal Caco-2 cell line.
2001 Sep 11
Susceptibility to the ototoxic properties of toluene is species specific.
2002 Apr
An MCASE approach to the search of a cure for Parkinson's Disease.
2002 Apr 2
Composition of the volatiles from intact and mechanically pierced tea aphid-tea shoot complexes and their attraction to natural enemies of the tea aphid.
2002 Apr 24
Identification of a protein-promoting vibration in the reaction catalyzed by horse liver alcohol dehydrogenase.
2002 Apr 3
Preparation of soluble and insoluble polymer supported IBX reagents.
2002 Aug 5
The effect of the nature of H-bonding groups on diffusion through PDMS membranes saturated with octanol and toluene.
2002 Feb
Disposition of 1-[3-(aminomethyl)phenyl]-N-[3-fluoro-2'- (methylsulfonyl)-[1,1'-biphenyl]-4-yl]-3-(trifluoromethyl)- 1H-pyrazole-5-carboxamide (DPC 423) by novel metabolic pathways. Characterization of unusual metabolites by liquid chromatography/mass spectrometry and NMR.
2002 Jan
Flash photolytic generation of o-quinone alpha-phenylmethide and o-quinone alpha-(p-anisyl)methide in aqueous solution and investigation of their reactions in that medium. Saturation of acid-catalyzed hydration.
2002 Jan 30
Effects of butylated hydroxyanisole and butylated hydroxytoluene on DNA adduct formation and arylamine N-acetyltransferase activity in human bladder tumour cells.
2002 Jan-Feb
Mineralization of aromatic compounds by brown-rot basidiomycetes - mechanisms involved in initial attack on the aromatic ring.
2002 Jun
Copper-catalyzed coupling of aryl iodides with aliphatic alcohols.
2002 Mar 21
Yeast-mediated preparation of l-PAC in an organic solvent.
2002 Mar 30
Catalytic degradation of CH2O and C6H5CH2OH in wastewaters.
2002 May
The mediation of veratryl alcohol in oxidations promoted by lignin peroxidase: the lifetime of veratryl alcohol radical cation.
2002 May 3

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Benzyl alcohol is applied as 5% lotion.
4-48 oz (depending on hair lenght) for 7 days
Route of Administration: Topical
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:52:49 UTC 2023
Edited
by admin
on Wed Jul 05 22:52:49 UTC 2023
Record UNII
LKG8494WBH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Benzyl alcohol
DASH   EP   FCC   FHFI   HSDB   II   INCI   INN   MART.   MI   ORANGE BOOK   USP-RS   VANDF   WHO-DD   WHO-IP  
INN   INCI  
Official Name English
BENZYL ALCOHOL [MI]
Common Name English
(HYDROXYMETHYL)BENZENE
Systematic Name English
ALCOHOL,BENZYL
VANDF  
Common Name English
BENZYL ALCOHOL [MART.]
Common Name English
BENZYL ALCOHOL [FHFI]
Common Name English
INS NO.1519
Code English
FEMA NO. 2137
Code English
BENZYL ALCOHOL [WHO-IP]
Common Name English
ULESFIA
Brand Name English
BENZYL ALCOHOL [ORANGE BOOK]
Common Name English
E-1519
Code English
ALCOHOL BENZYLICUS [WHO-IP LATIN]
Common Name English
ALCOHOL, BENZYL
Systematic Name English
BENZYL ALCOHOL [HSDB]
Common Name English
BENZYL ALCOHOL [JAN]
Common Name English
PHENYLCARBINOL
Systematic Name English
BENZALKONIUM CHLORIDE IMPURITY A [EP IMPURITY]
Common Name English
benzyl alcohol [INN]
Common Name English
BENZYL ALCOHOL [USP-RS]
Common Name English
BENZYL ALCOHOL [II]
Common Name English
BENZYL ALCOHOL [FCC]
Common Name English
NSC-8044
Code English
BENZYL ALCOHOL [EP MONOGRAPH]
Common Name English
BENZYL ALCOHOL [INCI]
Common Name English
ALCOHOL,BENZYL [VANDF]
Common Name English
INS-1519
Code English
Benzyl alcohol [WHO-DD]
Common Name English
BENZYL ALCOHOL [VANDF]
Common Name English
BENZENEMETHANOL
Systematic Name English
.ALPHA.-HYDROXYTOLUENE
Systematic Name English
Classification Tree Code System Code
JECFA EVALUATION BENZYL ALCOHOL
Created by admin on Wed Jul 05 22:52:49 UTC 2023 , Edited by admin on Wed Jul 05 22:52:49 UTC 2023
NCI_THESAURUS C28394
Created by admin on Wed Jul 05 22:52:50 UTC 2023 , Edited by admin on Wed Jul 05 22:52:50 UTC 2023
NDF-RT N0000181811
Created by admin on Wed Jul 05 22:52:50 UTC 2023 , Edited by admin on Wed Jul 05 22:52:50 UTC 2023
JECFA EVALUATION INS-1519
Created by admin on Wed Jul 05 22:52:50 UTC 2023 , Edited by admin on Wed Jul 05 22:52:50 UTC 2023
EC SCIENTIFIC COMMITTEE ON CONSUMER SAFETY OPINION SCCS/1459/11
Created by admin on Wed Jul 05 22:52:49 UTC 2023 , Edited by admin on Wed Jul 05 22:52:49 UTC 2023
EPA PESTICIDE CODE 9502
Created by admin on Wed Jul 05 22:52:49 UTC 2023 , Edited by admin on Wed Jul 05 22:52:49 UTC 2023
WHO-ATC P03AX06
Created by admin on Wed Jul 05 22:52:49 UTC 2023 , Edited by admin on Wed Jul 05 22:52:49 UTC 2023
CFR 21 CFR 172.515
Created by admin on Wed Jul 05 22:52:49 UTC 2023 , Edited by admin on Wed Jul 05 22:52:49 UTC 2023
Code System Code Type Description
WIKIPEDIA
BENZYL ALCOHOL
Created by admin on Wed Jul 05 22:52:50 UTC 2023 , Edited by admin on Wed Jul 05 22:52:50 UTC 2023
PRIMARY
EPA CompTox
DTXSID5020152
Created by admin on Wed Jul 05 22:52:49 UTC 2023 , Edited by admin on Wed Jul 05 22:52:49 UTC 2023
PRIMARY
NSC
8044
Created by admin on Wed Jul 05 22:52:50 UTC 2023 , Edited by admin on Wed Jul 05 22:52:50 UTC 2023
PRIMARY
NCI_THESAURUS
C77028
Created by admin on Wed Jul 05 22:52:50 UTC 2023 , Edited by admin on Wed Jul 05 22:52:50 UTC 2023
PRIMARY
CHEBI
17987
Created by admin on Wed Jul 05 22:52:49 UTC 2023 , Edited by admin on Wed Jul 05 22:52:49 UTC 2023
PRIMARY
MERCK INDEX
M2397
Created by admin on Wed Jul 05 22:52:50 UTC 2023 , Edited by admin on Wed Jul 05 22:52:50 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
202-859-9
Created by admin on Wed Jul 05 22:52:49 UTC 2023 , Edited by admin on Wed Jul 05 22:52:49 UTC 2023
PRIMARY
DAILYMED
LKG8494WBH
Created by admin on Wed Jul 05 22:52:49 UTC 2023 , Edited by admin on Wed Jul 05 22:52:49 UTC 2023
PRIMARY
SMS_ID
100000086395
Created by admin on Wed Jul 05 22:52:50 UTC 2023 , Edited by admin on Wed Jul 05 22:52:50 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
BENZYL ALCOHOL
Created by admin on Wed Jul 05 22:52:50 UTC 2023 , Edited by admin on Wed Jul 05 22:52:50 UTC 2023
PRIMARY Description: A clear, colourless, oily liquid; odour, slightly aromatic. Solubility: Soluble in water; miscible with ethanol (~750 g/l) TS, ether R, fatty and essential oils. Category: Antimicrobial preservative. Storage: Benzyl alcohol should be kept in a tightly closed container, protected from light. Additional information: Benzyl alcohol is affected by air and light, and should be protected from exposure to excessive heat.
CAS
100-51-6
Created by admin on Wed Jul 05 22:52:49 UTC 2023 , Edited by admin on Wed Jul 05 22:52:49 UTC 2023
PRIMARY
ChEMBL
CHEMBL720
Created by admin on Wed Jul 05 22:52:49 UTC 2023 , Edited by admin on Wed Jul 05 22:52:49 UTC 2023
PRIMARY
DRUG BANK
DB06770
Created by admin on Wed Jul 05 22:52:49 UTC 2023 , Edited by admin on Wed Jul 05 22:52:49 UTC 2023
PRIMARY
EVMPD
SUB05771MIG
Created by admin on Wed Jul 05 22:52:49 UTC 2023 , Edited by admin on Wed Jul 05 22:52:49 UTC 2023
PRIMARY
DRUG CENTRAL
334
Created by admin on Wed Jul 05 22:52:49 UTC 2023 , Edited by admin on Wed Jul 05 22:52:49 UTC 2023
PRIMARY
HSDB
45
Created by admin on Wed Jul 05 22:52:49 UTC 2023 , Edited by admin on Wed Jul 05 22:52:49 UTC 2023
PRIMARY
MESH
D019905
Created by admin on Wed Jul 05 22:52:50 UTC 2023 , Edited by admin on Wed Jul 05 22:52:50 UTC 2023
PRIMARY
INN
923
Created by admin on Wed Jul 05 22:52:49 UTC 2023 , Edited by admin on Wed Jul 05 22:52:49 UTC 2023
PRIMARY
RS_ITEM_NUM
1061901
Created by admin on Wed Jul 05 22:52:50 UTC 2023 , Edited by admin on Wed Jul 05 22:52:50 UTC 2023
PRIMARY
RXCUI
1426
Created by admin on Wed Jul 05 22:52:50 UTC 2023 , Edited by admin on Wed Jul 05 22:52:50 UTC 2023
PRIMARY RxNorm
PUBCHEM
244
Created by admin on Wed Jul 05 22:52:50 UTC 2023 , Edited by admin on Wed Jul 05 22:52:50 UTC 2023
PRIMARY
FDA UNII
LKG8494WBH
Created by admin on Wed Jul 05 22:52:49 UTC 2023 , Edited by admin on Wed Jul 05 22:52:49 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
http://apps.who.int/phint/pdf/b/Jb.6.1.50.pdf