You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameBenzyl alcohol
Accession NumberDB06770
TypeSmall Molecule
GroupsApproved
DescriptionNot Available
Structure
Thumb
Synonyms
(Hydroxymethyl)benzene
Alcoholum benzylicum
Alcool benzylique
Alcoolbenzylique
alpha-Hydroxytoluene
alpha-Toluenol
Aromatic alcohol
Bentalol
Benzalalcohol
Benzalcohol
Benzenecarbinol
Benzenemethanol
Benzoyl alcohol
Benzyl alcohol
Benzylalkohol
Benzylic alcohol
Hydroxymethylbenzene
Phenylcarbinol
Phenylmethanol
Phenylmethyl alcohol
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Babys Own Gora Teething Lotlotion25 mgG.T. Fulford Pharmaceuticals1961-12-311998-06-25Canada
Babys Own Teething Gelgel25 mgG.T. Fulford Pharmaceuticals1977-12-311998-06-25Canada
Ulesfialotion50 mg/gtopicalZylera Pharmaceuticals, LLC2014-07-16Not applicableUs
Ulesfialotion50 mg/gtopicalLachlan Pharmaceuticals2015-08-17Not applicableUs
Ulesfialotion50 mg/gtopicalShionogi Inc.2009-05-26Not applicableUs
Ulesfialotion50 mg/gtopicalConcordia Pharmaceuticals Inc.2009-05-26Not applicableUs
Approved Generic Prescription ProductsNot Available
Approved Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Averteaxcream10 mg/gtopicalCamellix, LLC2014-01-01Not applicableUs
Baby's Own Teething Gel - 2.5%gel2.5 %topicalBlock Drug Company (Canada) Ltd.1998-03-022001-03-14Canada
Baby's Own Teething Gel 2.5%gel2.5 %topicalDannorth Laboratories Inc.1990-12-311997-08-12Canada
Zilactin Early Relief Cold Soregel.1 g/gtopicalBlairex Laboratories, Inc.2005-06-30Not applicableUs
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixtures
NameLabellerIngredients
Biochemistry Pain Relief Foot ActivePure Source, Inc.
Cipro HCStat Rx USA
Denture Orajel GelCommerce Pharmaceutics Inc.
Foille OntBlistex Corporation
Itch XBF ASCHER AND CO INC
Itch X GelB.F. Ascher & Company Inc.
Itch-XBF ASCHER AND CO INC
Itch-X GelB.F. Ascher & Company Inc.
IvarestBlistex Inc
Ivy DryIvy Dry, Inc.
Ivy-dry SuperIvy Dry, Inc.
NitrotanCramer Products Inc
Shing-releevTopical Pharmaceuticals Inc.
Thomas Formula No 17Thomas Hair And Scalp Specialists
Thomas Formula No 47Thomas Hair And Scalp Specialists
SaltsNot Available
Categories
UNIILKG8494WBH
CAS number100-51-6
WeightAverage: 108.1378
Monoisotopic: 108.057514878
Chemical FormulaC7H8O
InChI KeyInChIKey=WVDDGKGOMKODPV-UHFFFAOYSA-N
InChI
InChI=1S/C7H8O/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2
IUPAC Name
phenylmethanol
SMILES
OCC1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzyl alcohols
Direct ParentBenzyl alcohols
Alternative Parents
Substituents
  • Benzyl alcohol
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationUlesfia (benzyl alcohol) lotion is indicated for the topical treatment of head lice infestation in patients 6 months of age and older. Ulesfia Lotion does not have ovicidal activity.
PharmacodynamicsNot Available
Mechanism of actionBenzyl alcohol inhibits lice from closing their respiratory spiracles, allowing the vehicle to obstruct the spiracles and causing the lice to asphyxiate.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
Toxicity1250 mg/kg (rat, oral) LD50 400 mg/kg IPR-RAT LD50 2000 mg/kg SKN-RBT LD50 53 mg/kg IVN-RAT LD50 2500 mg/kg ORL-GPG LD50
Affected organisms
  • Head lice
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9906
Blood Brain Barrier+0.9698
Caco-2 permeable+0.8859
P-glycoprotein substrateNon-substrate0.8373
P-glycoprotein inhibitor INon-inhibitor0.9803
P-glycoprotein inhibitor IINon-inhibitor0.9629
Renal organic cation transporterNon-inhibitor0.8259
CYP450 2C9 substrateNon-substrate0.7995
CYP450 2D6 substrateNon-substrate0.9234
CYP450 3A4 substrateNon-substrate0.8408
CYP450 1A2 substrateInhibitor0.5434
CYP450 2C9 inhibitorNon-inhibitor0.9285
CYP450 2D6 inhibitorNon-inhibitor0.9623
CYP450 2C19 inhibitorNon-inhibitor0.7859
CYP450 3A4 inhibitorNon-inhibitor0.9558
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8458
Ames testNon AMES toxic0.9645
CarcinogenicityNon-carcinogens0.5381
BiodegradationReady biodegradable0.8774
Rat acute toxicity1.9753 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8998
hERG inhibition (predictor II)Non-inhibitor0.9625
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Creamtopical10 mg/g
Geltopical2.5 %
Lotion25 mg
Gel25 mg
Suspensionauricular (otic)
Gelbuccal; topical
Ointmenttopical
Geltopical
Spraytopical
Creamtopical
Aerosol, spraytopical
Liquidtopical
Lotiontopical50 mg/g
Geltopical.1 g/g
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5858383 No1997-08-112017-08-11Us
US6139859 No1997-08-112017-08-11Us
US6793931 No2002-07-112022-07-11Us
US7294342 No2004-05-192024-05-19Us
Properties
StateLiquid
Experimental Properties
PropertyValueSource
melting point-15..2 °C, 258 K, 5 °F# http://sitem.herts.ac.uk/aeru/footprint/en/Reports/953.htm.
boiling point205.3 °C, 478 K, 402 °F# http://sitem.herts.ac.uk/aeru/footprint/en/Reports/953.htm.
water solubility33 mg/mL, clear, colorless# http://www.chemicalbook.com/ProductChemicalPropertiesCB3852587_EN.htm
logP1.1# http://sitem.herts.ac.uk/aeru/footprint/en/Reports/953.htm.
pKa15.4# http://sitem.herts.ac.uk/aeru/footprint/en/Reports/953.htm.
Predicted Properties
PropertyValueSource
Water Solubility26.8 mg/mLALOGPS
logP1.07ALOGPS
logP1.21ChemAxon
logS-0.61ALOGPS
pKa (Strongest Acidic)15.02ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.87 m3·mol-1ChemAxon
Polarizability11.89 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.19 KB)
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-00ko-6900000000-a9d668ecd37a1579a6feView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0a4i-9500000000-2a82c3dd7c6871f61c34View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0006-9000000000-ad1762d5292c30b29bbdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0006-9000000000-3c8d4c630cf42e3bfd3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-056r-9400000000-c4dcb2148958f946cd01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positivesplash10-056r-9400000000-e17e577dbe4546313a91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , Positivesplash10-056r-9300000000-fb124b56257906cce9f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-056r-9400000000-47b3605316c57e02b84fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-056r-9400000000-dd0878988e7c2d9a5431View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-3a71c23796a048eb999cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-40737e7bdf548d714249View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9100000000-23e82914cfa9372ecafcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1900000000-17f95f5a398b5850abb2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-7900000000-733d283e0916e755a736View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-d0c6e5fc39516ee594b4View in MoNA
MSMass Spectrum (Electron Ionization)splash10-056r-9400000000-a8f1fd78fa3f8781f296View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
Synthesis Reference

Cornelis Jongsma, Leon H. B. Frijns, Paula A. M. Raven-Donners, “Method for the preparation of a pure alkali metal benzoate and benzyl alcohol.” U.S. Patent US4296245, issued June, 1940.

US4296245
General References
  1. Taylor PM, Chengelis CP, Miller WR, Parker GA, Gleason TR, Cozzi E: Evaluation of propofol containing 2% benzyl alcohol preservative in cats. J Feline Med Surg. 2012 Aug;14(8):516-26. doi: 10.1177/1098612X12440354. Epub 2012 Feb 24. [PubMed:22366290 ]
  2. Novak E, Stubbs SS, Sanborn EC, Eustice RM: The tolerance and safety of intravenously administered benzyl alcohol in methylprednisolone sodium succinate formulations in normal human subjects. Toxicol Appl Pharmacol. 1972 Sep;23(1):54-61. [PubMed:4560999 ]
  3. Meinking TL, Villar ME, Vicaria M, Eyerdam DH, Paquet D, Mertz-Rivera K, Rivera HF, Hiriart J, Reyna S: The clinical trials supporting benzyl alcohol lotion 5% (Ulesfia): a safe and effective topical treatment for head lice (pediculosis humanus capitis). Pediatr Dermatol. 2010 Jan-Feb;27(1):19-24. doi: 10.1111/j.1525-1470.2009.01059.x. [PubMed:20199404 ]
External Links
ATC CodesP03AX06
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (1.05 MB)
MSDSDownload (50.6 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Nakajima T, Wang RS, Elovaara E, Gonzalez FJ, Gelboin HV, Raunio H, Pelkonen O, Vainio H, Aoyama T: Toluene metabolism by cDNA-expressed human hepatic cytochrome P450. Biochem Pharmacol. 1997 Feb 7;53(3):271-7. [PubMed:9065730 ]
  2. Kim H, Wang RS, Elovaara E, Raunio H, Pelkonen O, Aoyama T, Vainio H, Nakajima T: Cytochrome P450 isozymes responsible for the metabolism of toluene and styrene in human liver microsomes. Xenobiotica. 1997 Jul;27(7):657-65. [PubMed:9253143 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Vitamin d 24-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
References
  1. Furman GM, Silverman DM, Schatz RA: Inhibition of rat lung mixed-function oxidase activity following repeated low-level toluene inhalation: possible role of toluene metabolites. J Toxicol Environ Health A. 1998 Aug 21;54(8):633-45. [PubMed:9726784 ]
  2. Nakajima T, Wang RS, Elovaara E, Gonzalez FJ, Gelboin HV, Raunio H, Pelkonen O, Vainio H, Aoyama T: Toluene metabolism by cDNA-expressed human hepatic cytochrome P450. Biochem Pharmacol. 1997 Feb 7;53(3):271-7. [PubMed:9065730 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Electron carrier activity
Specific Function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular Weight:
56380.93 Da
References
  1. Kawamoto T, Koga M, Murata K, Matsuda S, Kodama Y: Effects of ALDH2, CYP1A1, and CYP2E1 genetic polymorphisms and smoking and drinking habits on toluene metabolism in humans. Toxicol Appl Pharmacol. 1995 Aug;133(2):295-304. [PubMed:7645026 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular Weight:
56277.81 Da
References
  1. Nakajima T, Wang RS, Elovaara E, Gonzalez FJ, Gelboin HV, Raunio H, Pelkonen O, Vainio H, Aoyama T: Toluene metabolism by cDNA-expressed human hepatic cytochrome P450. Biochem Pharmacol. 1997 Feb 7;53(3):271-7. [PubMed:9065730 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Nakajima T, Wang RS, Elovaara E, Gonzalez FJ, Gelboin HV, Raunio H, Pelkonen O, Vainio H, Aoyama T: Toluene metabolism by cDNA-expressed human hepatic cytochrome P450. Biochem Pharmacol. 1997 Feb 7;53(3):271-7. [PubMed:9065730 ]
  2. Kim H, Wang RS, Elovaara E, Raunio H, Pelkonen O, Aoyama T, Vainio H, Nakajima T: Cytochrome P450 isozymes responsible for the metabolism of toluene and styrene in human liver microsomes. Xenobiotica. 1997 Jul;27(7):657-65. [PubMed:9253143 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular Weight:
56848.42 Da
References
  1. Nakajima T, Wang RS, Elovaara E, Gonzalez FJ, Gelboin HV, Raunio H, Pelkonen O, Vainio H, Aoyama T: Toluene metabolism by cDNA-expressed human hepatic cytochrome P450. Biochem Pharmacol. 1997 Feb 7;53(3):271-7. [PubMed:9065730 ]
  2. Lipscomb JC, Barton HA, Tornero-Velez R, Evans MV, Alcasey S, Snawder JE, Laskey J: The metabolic rate constants and specific activity of human and rat hepatic cytochrome P-450 2E1 toward toluene and chloroform. J Toxicol Environ Health A. 2004 Apr 9;67(7):537-53. [PubMed:15129551 ]
  3. Kim H, Wang RS, Elovaara E, Raunio H, Pelkonen O, Aoyama T, Vainio H, Nakajima T: Cytochrome P450 isozymes responsible for the metabolism of toluene and styrene in human liver microsomes. Xenobiotica. 1997 Jul;27(7):657-65. [PubMed:9253143 ]
  4. Wang RS, Nakajima T, Park SS, Gelboin HV, Murayama N: Monoclonal antibody-directed assessment of toluene induction of rat hepatic cytochrome P450 isozymes. Biochem Pharmacol. 1993 Aug 3;46(3):413-9. [PubMed:8347164 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular Weight:
55768.94 Da
References
  1. Obach RS: Mechanism of cytochrome P4503A4- and 2D6-catalyzed dehydrogenation of ezlopitant as probed with isotope effects using five deuterated analogs. Drug Metab Dispos. 2001 Dec;29(12):1599-607. [PubMed:11717179 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Obach RS: Mechanism of cytochrome P4503A4- and 2D6-catalyzed dehydrogenation of ezlopitant as probed with isotope effects using five deuterated analogs. Drug Metab Dispos. 2001 Dec;29(12):1599-607. [PubMed:11717179 ]
Comments
comments powered by Disqus
Drug created on September 14, 2010 10:21 / Updated on June 24, 2016 01:49