Benzyl alcohol

Overview

Description
A medication used to treat head lice infections.
Description
A medication used to treat head lice infections.
DrugBank ID
DB06770
Type
Small Molecule
US Approved
YES
Other Approved
YES
Clinical Trials
Phase 0
0
Phase 1
4
Phase 2
6
Phase 3
5
Phase 4
10
Therapeutic Categories
  • Pediculicides

Identification

Summary

Benzyl alcohol is an antiparasitic agent used for the topical treatment of head lice infestation in patients 6 months of age and older.

Brand Names
Cipro, Cipro HC, Itch-X, Ivy-dry Cream, Ulesfia, Zilactin Cold Sore
Generic Name
Benzyl alcohol
DrugBank Accession Number
DB06770
Background

Not Available

Type
Small Molecule
Groups
Approved
Structure
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofCold sore••• ••••••••
Symptomatic treatment ofFever blister••• ••••••••
Treatment ofHead lice••••••••••••••••••
Used in combination to treatInsect bitesCombination Product in combination with: Chloroxylenol (DB11121), Benzocaine (DB01086)••• ••••••••• ••••••••• •••••
Management ofOral pain••• ••••••
Contraindications & Blackbox Warnings
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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
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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

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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Benzyl alcohol is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Benzyl alcohol can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Benzyl alcohol can be increased when combined with Abatacept.
AbemaciclibThe risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Benzyl alcohol.
AbirateroneThe serum concentration of Benzyl alcohol can be increased when it is combined with Abiraterone.
Food Interactions
No interactions found.

Products

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dosage, form, labeller, route of administration, and marketing period.
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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
UlesfiaLotion50 mg/1gTopicalConcordia Pharmaceuticals Inc.2009-05-262016-07-22US flag
UlesfiaLotion50 mg/1gTopicalLachlan Pharmaceuticals2015-08-172020-03-31US flag
UlesfiaLotion50 mg/1gTopicalShionogi2009-05-262016-04-30US flag
UlesfiaLotion50 mg/1gTopicalCerecor, Inc.2014-07-16Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AverteaxCream10 mg/1gTopicalCamellix, LLC2014-01-01Not applicableUS flag
Baby's Own Teething Gel - 2.5%Gel2.5 %TopicalBlock Drug Company (Canada) Ltd.1998-03-022001-03-14Canada flag
Baby's Own Teething Gel 2.5%Gel2.5 %TopicalDannorth Laboratories Inc.1990-12-311997-08-12Canada flag
Babys Own Gora Teething LotLotion25 mg / mLDentalG.T. Fulford Pharmaceuticals1961-12-311998-06-25Canada flag
Babys Own Teething GelGel25 mg / gDentalG.T. Fulford Pharmaceuticals1977-12-311998-06-25Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AcyclovixBenzyl alcohol (0.1 g/1g) + Acyclovir (200 mg/1)KitOral; TopicalPrimary Pharmaceuticals, Inc.2020-09-20Not applicableUS flag
BEHEPTAL 20 DRAJEBenzyl alcohol (24 mg) + Cyanocobalamin (0.03 mg) + Dexpanthenol (5 mg) + Flavin mononucleotide (5 mg) + Nicotinamide (50 mg) + Pyridoxine hydrochloride (10 mg) + Thiamine hydrochloride (25 mg)Tablet, coatedOSEL İLAÇ SAN. VE TİC. A.Ş.1999-05-05Not applicableTurkey flag
biochemistry PAIN RELIEF FOOT ACTIVEBenzyl alcohol (190 mg/1mL) + Lidocaine hydrochloride (40 mg/1mL)LiquidTopicalPure Source, Llc2014-02-06Not applicableUS flag
BIOCICAR® CREMABenzyl alcohol (1 g) + Zinc oxide (5 g) + Zinc oxide (5 g)CreamTopicalBIOCHEM FARMACEUTICA DE COLOMBIA S.A. BIOCHEM S.A.2006-11-10Not applicableColombia flag
Carpal ComfortBenzyl alcohol (10 mg/100mL) + Lidocaine hydrochloride (4 mg/100mL)CreamTopicalComfort Lab, LP2019-07-10Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Hand SanitizerBenzyl alcohol (0.3 g/100mL) + Ethanol (62 mL/100mL) + Phenoxyethanol (0.3 g/100mL)GelTopicalLarry (Xiamen) Hi Tech Co., Ltd2020-04-01Not applicableUS flag

Categories

ATC Codes
P03AX06 — Benzyl alcohol
Drug Categories
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)
Affected organisms
  • Head lice

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
  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. [Article]
  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. [Article]
  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. [Article]
Human Metabolome Database
HMDB0003119
KEGG Drug
D00077
KEGG Compound
C03485
PubChem Compound
244
PubChem Substance
175427090
ChemSpider
13860335
RxNav
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 10 more
FDA label
Download (1.05 MB)
MSDS
Download (50.6 KB)

Clinical Trials

Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package
PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
Not AvailableActive Not RecruitingDiagnosticCancer / Infertility1somestatusstop reasonjust information to hide
Not AvailableCompletedNot AvailableInfertility1somestatusstop reasonjust information to hide
Not AvailableCompletedOtherRecurrent Prostate Cancer1somestatusstop reasonjust information to hide
Not AvailableCompletedTreatmentOutcome During r-hFSH and r-hLH Stimulation / Outcome During r-hFSH Stimulation1somestatusstop reasonjust information to hide
Not AvailableUnknown StatusNot AvailableIn Vitro Maturation of Oocytes1somestatusstop reasonjust information to hide

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
KitOral; Topical
CreamTopical10 mg/1g
GelTopical2.5 %
LotionDental25 mg / mL
GelDental25 mg / g
Tablet, coated
CreamTopical
SolutionParenteral10.000 mcg
SuspensionAuricular (otic)
GelBuccal; Topical
KitSubcutaneous
OintmentTopical
SolutionCutaneous
SolutionSubcutaneous75 UI
TabletOral
GelTopical
SprayTopical
Tablet, solubleOral
Aerosol, sprayTopical
SolutionOral
SolutionIntramuscular125.000 mg
GelTopical100 mg/1g
CreamPercutaneous; Topical; Transdermal
LiquidPercutaneous; Topical; Transdermal
SolutionTopical
LiquidTopical
SolutionIntravenous
SolutionIntravenous440.00 mg
LotionTopical50 mg/1g
GelTopical0.1 g/1g
SolutionIntravenous
Lozenge
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5858383No1999-01-122017-08-11US flag
US6139859No2000-10-312017-08-11US flag
US6793931No2004-09-212022-07-11US flag
US7294342No2007-11-132024-05-19US flag

Properties

State
Liquid
Experimental Properties
PropertyValueSource
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 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 FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
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)

Spectra

Mass Spec (NIST)
Download (7.19 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-00ko-6900000000-a9d668ecd37a1579a6fe
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-054o-9200000000-a9f7c0f39c81d478c0d4
GC-MS Spectrum - EI-BGC-MSsplash10-056r-9400000000-77cec715500da9c57a84
GC-MS Spectrum - EI-BGC-MSsplash10-056r-9400000000-8dc38068387df3fa06aa
GC-MS Spectrum - EI-BGC-MSsplash10-056r-9300000000-fb124b56257906cce9f1
GC-MS Spectrum - EI-BGC-MSsplash10-056r-9400000000-7a77e67486ae3b2dd855
GC-MS Spectrum - EI-BGC-MSsplash10-056r-9400000000-dd0878988e7c2d9a5431
GC-MS Spectrum - GC-MSGC-MSsplash10-00ko-6900000000-a9d668ecd37a1579a6fe
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0006-8900000000-c256b0b7a0755f08ac64
Mass Spectrum (Electron Ionization)MSsplash10-056r-9400000000-a8f1fd78fa3f8781f296
MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)LC-MS/MSsplash10-0a4i-9500000000-2a82c3dd7c6871f61c34
MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)LC-MS/MSsplash10-0006-9000000000-ad1762d5292c30b29bbd
MS/MS Spectrum - Quattro_QQQ 40V, N/ALC-MS/MSsplash10-0006-9000000000-3c8d4c630cf42e3bfd3f
MS/MS Spectrum - EI-B (HITACHI RMU-7M) , PositiveLC-MS/MSsplash10-056r-9400000000-c4dcb2148958f946cd01
MS/MS Spectrum - EI-B (HITACHI RMU-6M) , PositiveLC-MS/MSsplash10-056r-9400000000-e17e577dbe4546313a91
MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , PositiveLC-MS/MSsplash10-056r-9300000000-fb124b56257906cce9f1
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-056r-9400000000-47b3605316c57e02b84f
MS/MS Spectrum - EI-B (HITACHI M-80B) , PositiveLC-MS/MSsplash10-056r-9400000000-dd0878988e7c2d9a5431
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-3900000000-4d1bf15f6cf8f65bf0a6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-4cef0d66802e59e9ddfc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a6r-8900000000-d648082e6bb2d4bc0736
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-fa2400eebcfb7562d40a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9200000000-72dc044d901c3dfcec51
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-9000000000-8fb296960679d807efba
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-6b10a1cb91093a4b8eeb
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-118.0680568
predicted
DarkChem Lite v0.1.0
[M-H]-117.9780568
predicted
DarkChem Lite v0.1.0
[M-H]-118.0318568
predicted
DarkChem Lite v0.1.0
[M-H]-117.8641568
predicted
DarkChem Lite v0.1.0
[M-H]-119.23685
predicted
DeepCCS 1.0 (2019)
[M+H]+118.2260568
predicted
DarkChem Lite v0.1.0
[M+H]+118.7248568
predicted
DarkChem Lite v0.1.0
[M+H]+118.3885568
predicted
DarkChem Lite v0.1.0
[M+H]+118.3888568
predicted
DarkChem Lite v0.1.0
[M+H]+121.85543
predicted
DeepCCS 1.0 (2019)
[M+Na]+118.1308568
predicted
DarkChem Lite v0.1.0
[M+Na]+117.9773568
predicted
DarkChem Lite v0.1.0
[M+Na]+118.2113568
predicted
DarkChem Lite v0.1.0
[M+Na]+118.0858568
predicted
DarkChem Lite v0.1.0
[M+Na]+130.26768
predicted
DeepCCS 1.0 (2019)

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
Specific Function
arachidonic acid epoxygenase activity
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15041462, PubMed:15805301, PubMed:18577768, PubMed:19965576, PubMed:20972997). Catalyzes the hydroxylation of carbon-hydrogen bonds. Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C15-alpha and C16-alpha positions (PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15805301). Displays different regioselectivities for polyunsaturated fatty acids (PUFA) hydroxylation (PubMed:15041462, PubMed:18577768). Catalyzes the epoxidation of double bonds of certain PUFA (PubMed:15041462, PubMed:19965576, PubMed:20972997). Converts arachidonic acid toward epoxyeicosatrienoic acid (EET) regioisomers, 8,9-, 11,12-, and 14,15-EET, that function as lipid mediators in the vascular system (PubMed:20972997). Displays an absolute stereoselectivity in the epoxidation of eicosapentaenoic acid (EPA) producing the 17(R),18(S) enantiomer (PubMed:15041462). May play an important role in all-trans retinoic acid biosynthesis in extrahepatic tissues. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195)
Specific Function
arachidonic acid monooxygenase activity
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Required for clearance of cellular formaldehyde, a cytotoxic and carcinogenic metabolite that induces DNA damage
Specific Function
aldehyde dehydrogenase (NAD+) activity
Gene Name
ALDH2
Uniprot ID
P05091
Uniprot Name
Aldehyde dehydrogenase, mitochondrial
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)
Specific Function
aromatase activity
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58406.915 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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of fatty acids (PubMed:10553002, PubMed:18577768). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:10553002, PubMed:18577768). Catalyzes the hydroxylation of carbon-hydrogen bonds. Hydroxylates fatty acids specifically at the omega-1 position displaying the highest catalytic activity for saturated fatty acids (PubMed:10553002, PubMed:18577768). May be involved in the oxidative metabolism of xenobiotics (Probable)
Specific Function
4-nitrophenol 2-monooxygenase activity
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
A cytochrome P450 monooxygenase involved in the metabolism of fatty acids, steroids and retinoids (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:18698000, PubMed:19965576, PubMed:20972997, PubMed:21289075, PubMed:21576599). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:19965576, PubMed:20972997). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 20-hydroxyeicosatetraenoic acid ethanolamide (20-HETE-EA) and 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:18698000, PubMed:21289075). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Catalyzes the oxidative transformations of all-trans retinol to all-trans retinal, a precursor for the active form all-trans-retinoic acid (PubMed:10681376). Also involved in the oxidative metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants
Specific Function
anandamide 11,12 epoxidase activity
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
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. [Article]

Drug created at September 14, 2010 16:21 / Updated at November 05, 2024 02:22