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Identification
NameBenzyl alcohol
Accession NumberDB06770
Typesmall molecule
Groupsapproved
DescriptionNot Available
Structure
Thumb
Synonyms
SynonymLanguageCode
(Hydroxymethyl)benzeneNot AvailableNot Available
AlcoolbenzyliqueNot AvailableNot Available
BentalolNot AvailableNot Available
BenzalalcoholNot AvailableNot Available
BenzalcoholNot AvailableNot Available
BenzenemethanolNot AvailableNot Available
Benzoyl alcoholNot AvailableNot Available
PhenylmethanolNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
UlesfiaShionogi Inc.
Brand mixturesNot Available
Categories
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
Mass Specshow(7.19 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassNot Available
Direct parentBenzene and Substituted Derivatives
Alternative parentsPrimary Alcohols; Polyamines
Substituentspolyamine; primary alcohol; alcohol
Classification descriptionThis compound belongs to the benzene and substituted derivatives. These are aromatic compounds containing at least one benzene ring.
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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
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
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 substrate Non-inhibitor 0.9285
CYP450 2D6 substrate Non-inhibitor 0.9623
CYP450 2C19 substrate Non-inhibitor 0.7859
CYP450 3A4 substrate 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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
LotionTopical5%
PricesNot Available
Patents
CountryPatent NumberApprovedExpires (estimated)
United States72943422007-11-132024-05-19
United States67939312004-09-212022-07-11
United States61398592000-10-312017-08-11
United States58583831999-01-122017-08-11
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 solubility2.68e+01 g/lALOGPS
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 area20.23ChemAxon
rotatable bond count1ChemAxon
refractivity32.87ChemAxon
polarizability11.89ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
Spectra
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 Reference
  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
  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
  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.×. Pubmed 20199404
External Links
ResourceLink
KEGG DrugD00077
ChEBI17987
ChEMBLCHEMBL720
RxListhttp://www.rxlist.com/ulesfia-drug.htm
WikipediaBenzyl_alcohol
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelshow(1.05 MB)
MSDSshow(50.6 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

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
  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

2. Cytochrome P450 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

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
  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
  3. 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

3. Aldehyde dehydrogenase, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Aldehyde dehydrogenase, mitochondrial P05091 Details

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

4. Cytochrome P450 2B6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2B6 P20813 Details

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

5. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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
  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

6. Cytochrome P450 2E1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

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
  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
  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
  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

7. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

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

8. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

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
  2. 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
  3. 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

Comments
Drug created on September 14, 2010 10:21 / Updated on September 16, 2013 18:04