Benzyl alcohol
Explore a selection of our essential drug information below, or:
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
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 4
- Phase 2
- 6
- Phase 3
- 5
- Phase 4
- 10
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.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Cold sore ••• ••• ••••• Symptomatic treatment of Fever blister ••• ••• ••••• Treatment of Head lice •••••••••••• •••••• Used in combination to treat Insect bites Combination Product in combination with: Chloroxylenol (DB11121), Benzocaine (DB01086) ••• ••• •••••• ••••••••• ••••• Management of Oral pain ••• ••• ••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Benzyl alcohol is combined with 1,2-Benzodiazepine. Abametapir 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. Abemaciclib The risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Benzyl alcohol. Abiraterone The serum concentration of Benzyl alcohol can be increased when it is combined with Abiraterone. - Food Interactions
- No interactions found.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ulesfia 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 - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Averteax Cream 10 mg/1g Topical Camellix, LLC 2014-01-01 Not applicable US Baby's Own Teething Gel - 2.5% Gel 2.5 % Topical Block Drug Company (Canada) Ltd. 1998-03-02 2001-03-14 Canada Baby's Own Teething Gel 2.5% Gel 2.5 % Topical Dannorth Laboratories Inc. 1990-12-31 1997-08-12 Canada Babys Own Gora Teething Lot Lotion 25 mg / mL Dental G.T. Fulford Pharmaceuticals 1961-12-31 1998-06-25 Canada Babys Own Teething Gel Gel 25 mg / g Dental G.T. Fulford Pharmaceuticals 1977-12-31 1998-06-25 Canada - 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 BEHEPTAL 20 DRAJE Benzyl 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, coated OSEL İLAÇ SAN. VE TİC. A.Ş. 1999-05-05 Not applicable Turkey 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 BIOCICAR® CREMA Benzyl alcohol (1 g) + Zinc oxide (5 g) + Zinc oxide (5 g) Cream Topical BIOCHEM FARMACEUTICA DE COLOMBIA S.A. BIOCHEM S.A. 2006-11-10 Not applicable Colombia Carpal Comfort Benzyl alcohol (10 mg/100mL) + Lidocaine hydrochloride (4 mg/100mL) Cream Topical Comfort Lab, LP 2019-07-10 Not applicable US - 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
- Dental Agents
- Ectoparasiticides, Incl. Scabicides
- Ectoparasiticides, Incl. Scabicides, Insecticides and Repellents
- Miscellaneous Local Anti-infectives
- 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)
- 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
- 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]
- 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]
- 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]
- 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 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 Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Active Not Recruiting Diagnostic Cancer / Infertility 1 somestatus stop reason just information to hide Not Available Completed Not Available Infertility 1 somestatus stop reason just information to hide Not Available Completed Other Recurrent Prostate Cancer 1 somestatus stop reason just information to hide Not Available Completed Treatment Outcome During r-hFSH and r-hLH Stimulation / Outcome During r-hFSH Stimulation 1 somestatus stop reason just information to hide Not Available Unknown Status Not Available In Vitro Maturation of Oocytes 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Kit Oral; Topical Cream Topical 10 mg/1g Gel Topical 2.5 % Lotion Dental 25 mg / mL Gel Dental 25 mg / g Tablet, coated Cream Topical Solution Parenteral 10.000 mcg Suspension Auricular (otic) Gel Buccal; Topical Kit Subcutaneous Ointment Topical Solution Cutaneous Solution Subcutaneous 75 UI Tablet Oral Gel Topical Spray Topical Tablet, soluble Oral Aerosol, spray Topical Solution Oral Solution Intramuscular 125.000 mg Gel Topical 100 mg/1g Cream Percutaneous; Topical; Transdermal Liquid Percutaneous; Topical; Transdermal Solution Topical Liquid Topical Solution Intravenous Solution Intravenous 440.00 mg Lotion Topical 50 mg/1g Gel Topical 0.1 g/1g Solution Intravenous Lozenge - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5858383 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
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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 118.0680568 predictedDarkChem Lite v0.1.0 [M-H]- 117.9780568 predictedDarkChem Lite v0.1.0 [M-H]- 118.0318568 predictedDarkChem Lite v0.1.0 [M-H]- 117.8641568 predictedDarkChem Lite v0.1.0 [M-H]- 119.23685 predictedDeepCCS 1.0 (2019) [M+H]+ 118.2260568 predictedDarkChem Lite v0.1.0 [M+H]+ 118.7248568 predictedDarkChem Lite v0.1.0 [M+H]+ 118.3885568 predictedDarkChem Lite v0.1.0 [M+H]+ 118.3888568 predictedDarkChem Lite v0.1.0 [M+H]+ 121.85543 predictedDeepCCS 1.0 (2019) [M+Na]+ 118.1308568 predictedDarkChem Lite v0.1.0 [M+Na]+ 117.9773568 predictedDarkChem Lite v0.1.0 [M+Na]+ 118.2113568 predictedDarkChem Lite v0.1.0 [M+Na]+ 118.0858568 predictedDarkChem Lite v0.1.0 [M+Na]+ 130.26768 predictedDeepCCS 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
- 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]
- 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
- 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]
- 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
- 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
- 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]
- 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
- 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]
- 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]
- 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]
- 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
- 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