Benzyl alcohol
Identification
- Name
- Benzyl alcohol
- Accession Number
- DB06770
- Description
- Not Available
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Benzyl alcohol (DB06770)
- Weight
- Average: 108.1378
Monoisotopic: 108.057514878 - Chemical Formula
- C7H8O
- Synonyms
- (hydroxymethyl)benzene
- Alcoholum benzylicum
- Alcool benzylique
- Alcoolbenzylique
- alpha-Hydroxytoluene
- Aromatic alcohol
- Bentalol
- Benzalalcohol
- Benzalcohol
- Benzenecarbinol
- Benzenemethanol
- Benzoyl alcohol
- Benzyl alcohol
- Benzylalkohol
- Benzylic alcohol
- Hydroxymethylbenzene
- Phenylcarbinol
- Phenylmethanol
- Phenylmethyl alcohol
- α-toluenol
- External IDs
- E-1519
- FEMA NO. 2137
- INS NO.1519
- INS-1519
- NSC-8044
Pharmacology
- Indication
Ulesfia (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.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
- Not Available
- Mechanism of action
Benzyl alcohol inhibits lice from closing their respiratory spiracles, allowing the vehicle to obstruct the spiracles and causing the lice to asphyxiate.
- Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
1250 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
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbametapir The serum concentration of Benzyl alcohol can be increased when it is combined with Abametapir. Abatacept The metabolism of Benzyl alcohol can be increased when combined with Abatacept. Abiraterone The serum concentration of Benzyl alcohol can be increased when it is combined with Abiraterone. Acebutolol The metabolism of Benzyl alcohol can be decreased when combined with Acebutolol. Acenocoumarol The metabolism of Benzyl alcohol can be decreased when combined with Acenocoumarol. Acetaminophen Benzyl alcohol may increase the hepatotoxic activities of Acetaminophen. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Benzyl alcohol. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Benzyl alcohol. Aclidinium Benzyl alcohol may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Acyclovir The metabolism of Benzyl alcohol can be decreased when combined with Acyclovir. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataUlesfia Lotion 50 mg/1g Topical Concordia Pharmaceuticals, Inc 2009-05-26 2016-07-22 US 
Ulesfia Lotion 50 mg/1g Topical Lachlan Pharmaceuticals 2015-08-17 2020-03-31 US Ulesfia Lotion 50 mg/1g Topical Shionogi 2009-05-26 2016-04-30 US Ulesfia Lotion 50 mg/1g Topical Cerecor, Inc. 2014-07-16 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataAverteax Cream 10 mg/1g Topical Camellix, LLC 2014-01-01 Not applicable US Baby's Own Teething Gel - 2.5% Gel Topical Block Drug Company (Canada) Ltd. 1998-03-02 2001-03-14 Canada 
Baby's Own Teething Gel 2.5% Gel Topical Dannorth Laboratories Inc. 1990-12-31 1997-08-12 Canada Babys Own Gora Teething Lot Lotion Dental G.T. Fulford Pharmaceuticals 1961-12-31 1998-06-25 Canada Babys Own Teething Gel Gel Dental G.T. Fulford Pharmaceuticals 1977-12-31 1998-06-25 Canada Protocoxil Gel 100 mg/1g Topical Bio ekuiliber llc 2017-05-09 2018-11-30 US Protocoxil Gel 100 mg/1g Topical Bio ekuiliber llc 2017-05-09 2021-10-07 US Zilactin Early Relief Cold Sore Gel 0.1 g/1g Topical Blairex Laboratories, Inc. 2005-06-30 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Acyclovix Benzyl alcohol (0.1 g/1g) + Acyclovir (200 mg/1) Kit Oral; Topical Primary Pharmaceuticals, Inc. 2020-09-20 Not applicable US biochemistry PAIN RELIEF FOOT ACTIVE Benzyl alcohol (190 mg/1mL) + Lidocaine hydrochloride (40 mg/1mL) Liquid Topical Pure Source, Llc 2014-02-06 Not applicable US Carpal Comfort Benzyl alcohol (10 mg/100mL) + Lidocaine hydrochloride (4 mg/100mL) Cream Topical Comfort Lab, LP 2019-07-10 Not applicable US Cipro Benzyl alcohol (9 mg/1mL) + Ciprofloxacin hydrochloride (2 mg/1mL) + Hydrocortisone (10 mg/1mL) Suspension Auricular (otic) Physicians Total Care, Inc. 2009-02-12 Not applicable US Cipro HC Benzyl alcohol (9 mg/1mL) + Ciprofloxacin hydrochloride (2 mg/1mL) + Hydrocortisone (10 mg/1mL) Suspension Auricular (otic) Stat Rx USA 1998-02-10 Not applicable US CVS Maximum Strength LIDOCAINE PLUS Benzyl alcohol (10 g/100g) + Lidocaine hydrochloride (4 g/100g) Spray Topical CVS Pharmacy Inc. 2020-05-15 Not applicable US Denture Orajel Gel Benzyl alcohol (1 %) + Benzocaine (7.5 %) + Clove oil (0.2 %) Gel Buccal; Topical Commerce Pharmaceutics Inc. 1997-12-17 2004-07-20 Canada Enbrel Benzyl alcohol (9.93 mg/1mL) + Etanercept (25 mg/1mL) Kit Subcutaneous Physicians Total Care, Inc. 2003-04-30 2012-06-30 US Fast Freeze Lidocaine Roll-On Benzyl alcohol (10 mg/1mL) + Lidocaine hydrochloride (40 mg/1mL) Liquid Topical NATURAL ESSENTIALS, INC. 2020-07-10 Not applicable US Foille Ont Benzyl alcohol (4 %) + Benzocaine (2 %) Ointment Topical Blistex Corporation 1980-12-31 2007-07-10 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Hand Sanitizer Benzyl alcohol (0.3 g/100mL) + Ethanol (62 mL/100mL) + Phenoxyethanol (0.3 g/100mL) Gel Topical Larry (Xiamen)Hi-Tech Co.,Ltd. 2020-04-01 Not applicable US
Categories
- ATC Codes
- P03AX06 — Benzyl alcohol
- Drug Categories
- Alcohols
- Anesthetics
- Anesthetics, Local
- Antiparasitic Products, Insecticides and Repellents
- Benzene Derivatives
- Benzyl Alcohols
- Benzyl Compounds
- Central Nervous System Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP2E1 Substrates
- Cytochrome P-450 Substrates
- Ectoparasiticides, Incl. Scabicides
- Ectoparasiticides, Incl. Scabicides, Insecticides and Repellents
- Pediculicides
- Peripheral Nervous System Agents
- Sensory System Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzyl alcohols. These are organic compounds containing the phenylmethanol substructure.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzyl alcohols
- Direct Parent
- Benzyl alcohols
- Alternative Parents
- Primary alcohols / Hydrocarbon derivatives / Aromatic alcohols
- Substituents
- Alcohol / Aromatic alcohol / Aromatic homomonocyclic compound / Benzyl alcohol / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Primary alcohol
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- benzyl alcohols (CHEBI:17987) / an aromatic compound (BENZYL-ALCOHOL)
Chemical Identifiers
- UNII
- LKG8494WBH
- CAS number
- 100-51-6
- InChI Key
- 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
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
- 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]
- 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]
- 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
- Human Metabolome Database
- HMDB0003119
- KEGG Drug
- D00077
- KEGG Compound
- C03485
- PubChem Compound
- 244
- PubChem Substance
- 175427090
- ChemSpider
- 13860335
- 1426
- ChEBI
- 17987
- ChEMBL
- CHEMBL720
- ZINC
- ZINC000000895302
- PharmGKB
- PA448594
- PDBe Ligand
- 010
- RxList
- RxList Drug Page
- Wikipedia
- Benzyl_alcohol
- PDB Entries
- 2amq / 2hob / 2q6f / 3d23 / 3iwm / 4ii8 / 5eb5 / 5eu8 / 5gwy / 5gwz … show 5 more
- FDA label
- Download (1.05 MB)
- MSDS
- Download (50.6 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Hip Pain 1 3 Completed Treatment Head Lice Infestation 1 3 Completed Treatment Otitis Externa 1 2 Completed Treatment Head Lice Infestation 2 1 Completed Basic Science Alcohol Dependence / Alcohol Related Disorders 1 1 Completed Other Treatment Against the Lethal Effects of Nerve Agent Intoxication 1 1, 2 Completed Treatment Gingivitis 1 0 Suspended Basic Science Quadriceps Muscle 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Kit Oral; Topical Cream Topical 10 mg/1g Gel Topical Lotion Dental Gel Dental Tablet, coated 25 mg Cream Topical 1 g Cream Topical Lozenge 6 mg Suspension Auricular (otic) Gel Buccal; Topical Kit Subcutaneous Ointment Topical Cream Topical 5 g Solution Cutaneous 5 g Gel Topical Spray Topical Injection, solution 900 mg/100mL Tablet Oral 6.4 mg Tablet, soluble Oral 6.4 mg Aerosol, spray Topical Solution Oral Gel Topical 100 mg/1g Cream Percutaneous; Topical; Transdermal Liquid Percutaneous; Topical; Transdermal Liquid Topical Lotion Topical 50 mg/1g Gel Topical 0.1 g/1g - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region Unlock Additional DataUS5858383 No 1999-01-12 2017-08-11 US US6139859 No 2000-10-31 2017-08-11 US US6793931 No 2004-09-21 2022-07-11 US US7294342 No 2007-11-13 2024-05-19 US Additional Data Available- Filed On
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) -15..2 °C, 258 K, 5 °F # http://sitem.herts.ac.uk/aeru/footprint/en/Reports/953.htm. boiling point (°C) 205.3 °C, 478 K, 402 °F # http://sitem.herts.ac.uk/aeru/footprint/en/Reports/953.htm. water solubility 33 mg/mL, clear, colorless # http://www.chemicalbook.com/ProductChemicalPropertiesCB3852587_EN.htm logP 1.1 # http://sitem.herts.ac.uk/aeru/footprint/en/Reports/953.htm. pKa 15.4 # http://sitem.herts.ac.uk/aeru/footprint/en/Reports/953.htm. - Predicted Properties
Property Value Source Water Solubility 26.8 mg/mL ALOGPS logP 1.07 ALOGPS logP 1.21 ChemAxon logS -0.61 ALOGPS pKa (Strongest Acidic) 15.02 ChemAxon pKa (Strongest Basic) -2.8 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 20.23 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 32.87 m3·mol-1 ChemAxon Polarizability 11.89 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9906 Blood Brain Barrier + 0.9698 Caco-2 permeable + 0.8859 P-glycoprotein substrate Non-substrate 0.8373 P-glycoprotein inhibitor I Non-inhibitor 0.9803 P-glycoprotein inhibitor II Non-inhibitor 0.9629 Renal organic cation transporter Non-inhibitor 0.8259 CYP450 2C9 substrate Non-substrate 0.7995 CYP450 2D6 substrate Non-substrate 0.9234 CYP450 3A4 substrate Non-substrate 0.8408 CYP450 1A2 substrate Inhibitor 0.5434 CYP450 2C9 inhibitor Non-inhibitor 0.9285 CYP450 2D6 inhibitor Non-inhibitor 0.9623 CYP450 2C19 inhibitor Non-inhibitor 0.7859 CYP450 3A4 inhibitor Non-inhibitor 0.9558 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8458 Ames test Non AMES toxic 0.9645 Carcinogenicity Non-carcinogens 0.5381 Biodegradation Ready biodegradable 0.8774 Rat acute toxicity 1.9753 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8998 hERG inhibition (predictor II) Non-inhibitor 0.9625
Spectra
- Mass Spec (NIST)
- Download (7.19 KB)
- Spectra
Enzymes
- Kind
- Protein
- Organism
- Humans
- 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 un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- 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]
- 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
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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 un...
- Gene Name
- CYP1A1
- Uniprot ID
- P04798
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 58164.815 Da
References
- 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]
- 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
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Electron carrier activity
- Specific Function
- Not Available
- Gene Name
- ALDH2
- Uniprot ID
- P05091
- Uniprot Name
- Aldehyde dehydrogenase, mitochondrial
- Molecular Weight
- 56380.93 Da
References
- 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
- Humans
- 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 un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- 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]
- 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
- Humans
- 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 ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- 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]
- 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]
- 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]
- 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
- Humans
- 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...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- 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]
Drug created on September 14, 2010 10:21 / Updated on June 12, 2020 10:52
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