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Identification
- Summary
Methoxsalen is a furocoumarin used to treat psoriasis and vitiligo.
- Brand Names
- Oxsoralen, Uvadex
- Generic Name
- Methoxsalen
- DrugBank Accession Number
- DB00553
- Background
A naturally occurring furocoumarin compound found in several species of plants, including Psoralea corylifolia. It is a photoactive substance that forms DNA adducts in the presence of ultraviolet A irradiation.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Methoxsalen (DB00553)
- Weight
- Average: 216.192
Monoisotopic: 216.042258738 - Chemical Formula
- C12H8O4
- Synonyms
- 6-hydroxy-7-methoxy-5-benzofuranacrylic acid δ-lactone
- 8-methoxy-[furano-3'.2':6.7-coumarin]
- 8-methoxy-2',3',6,7-furocoumarin
- 8-methoxy-4',5':6,7-furocoumarin
- 8-Methoxyfuranocoumarin
- 8-methoxypsoralen
- 8-MOP
- 8-MP
- 9-methoxy-7H-furo[3,2-g][1]benzopyran-7-one
- Ammoidin
- Methoxsalen
- Méthoxsalène
- Metoxaleno
- O-methylxanthotoxol
- Xanthotoxin
- Xanthotoxine
- External IDs
- NSC-45923
Pharmacology
- Indication
For the treatment of psoriasis and vitiligo
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 Treatment of Cutaneous t-cell lymphoma (ctcl) •••••••••••• •••••••••• •••• •••••••• Symptomatic treatment of Refractory cutaneous t-cell lymphoma •••••••••••• •••••••••• •••••••• Treatment of Vitiligo ••• ••• •••••• •••••••• Symptomatic treatment of Idiopathic vitiligo •••••••••••• Management of Severe psoriasis •••••••••••• - 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
Methoxsalen selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content correlates with the degree of Methoxsalen-induced cross-linking. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed.
- Mechanism of action
After activation it binds preferentially to the guanine and cytosine moieties of DNA, leading to cross-linking of DNA, thus inhibiting DNA synthesis and function.
Target Actions Organism ADNA intercalationHumans ACytochrome P450 2A6 binderHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
In both mice and man, methoxsalen is rapidly metabolized. Approximately 95% of the drug is excreted as a series of metabolites in the urine within 24 hours (Pathak et al. 1977).
- Half-life
Approximately 2 hours
- 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
Not Available
- 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 softwareAbacavir Methoxsalen may decrease the excretion rate of Abacavir which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Methoxsalen which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Methoxsalen which could result in a higher serum level. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Methoxsalen. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Methoxsalen. - Food Interactions
- Take with food. Take this medication with food or milk.
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.- Product Images
- International/Other Brands
- Deltasoralen (Delta) / Meladinine (CLS Pharma) / Meloxine / Ultra Mop
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image 8-mop Capsule, gelatin coated 10 mg/1 Oral Valeant Pharmaceuticals North America 1954-12-03 2017-08-31 US 
Oxsoralen Lotion 10 mg/1mL Topical Valeant Pharmaceuticals North America 1954-12-03 2016-06-30 US Oxsoralen Cap 10mg Capsule 10 mg Oral Valeant Canada Lp Valeant Canada S.E.C. 1992-12-31 2015-08-05 Canada 
Oxsoralen Lot 10mg/ml Lotion 10 mg / mL Topical Valeant Canada Lp Valeant Canada S.E.C. 1992-12-31 2015-08-05 Canada Oxsoralen-Ultra Capsule, liquid filled 10 mg/1 Oral Bausch Health, Canada Inc. 1986-10-30 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Methoxsalen Capsule, liquid filled 10 mg/1 Oral Oceanside Pharmaceuticals 2014-07-15 Not applicable US 
Methoxsalen Capsule, liquid filled 10 mg/1 Oral Actavis Pharma, Inc. 2016-09-14 Not applicable US Methoxsalen Capsule, liquid filled 10 mg/1 Oral Strides Pharma Science Limited 2016-12-08 Not applicable US
Categories
- ATC Codes
- D05BA02 — Methoxsalen
- D05BA — Psoralens for systemic use
- D05B — ANTIPSORIATICS FOR SYSTEMIC USE
- D05 — ANTIPSORIATICS
- D — DERMATOLOGICALS
- Drug Categories
- Antipsoriatics
- Antipsoriatics for Systemic Use
- Antipsoriatics for Topical Use
- Benzopyrans
- Coloring Agents
- Compounds used in a research, industrial, or household setting
- Cross-Linking Reagents
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2A6 Inhibitors
- Cytochrome P-450 CYP2A6 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Dermatologicals
- Drugs that are Mainly Renally Excreted
- Furocoumarins
- Heterocyclic Compounds, Fused-Ring
- Indicators and Reagents
- Laboratory Chemicals
- Photoabsorption
- Photoactivated Radical Generator
- Photosensitizing Activity
- Photosensitizing Agents
- Photosensitizing Agents for Phototherapy
- Psoralens for Systemic Use
- Psoralens for Topical Use
- Pyrans
- Radiation-Sensitizing Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Coumarins and derivatives
- Sub Class
- Furanocoumarins
- Direct Parent
- 8-methoxypsoralens
- Alternative Parents
- 1-benzopyrans / Benzofurans / Anisoles / Pyranones and derivatives / Alkyl aryl ethers / Heteroaromatic compounds / Furans / Lactones / Oxacyclic compounds / Organic oxides show 1 more
- Substituents
- 1-benzopyran / 8-methoxypsoralen / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Benzenoid / Benzofuran / Benzopyran / Ether / Furan show 10 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- aromatic ether, psoralens (CHEBI:18358) / Polyketides, Furanocoumarins (C01864) / an 8-methoxyfurocoumarin (CPD-13042)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- U4VJ29L7BQ
- CAS number
- 298-81-7
- InChI Key
- QXKHYNVANLEOEG-UHFFFAOYSA-N
- InChI
- InChI=1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3
- IUPAC Name
- 9-methoxy-7H-furo[3,2-g]chromen-7-one
- SMILES
- COC1=C2OC(=O)C=CC2=CC2=C1OC=C2
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014693
- KEGG Drug
- D00139
- KEGG Compound
- C01864
- PubChem Compound
- 4114
- PubChem Substance
- 46506275
- ChemSpider
- 3971
- BindingDB
- 50041234
- 6854
- ChEBI
- 18358
- ChEMBL
- CHEMBL416
- ZINC
- ZINC000002548959
- Therapeutic Targets Database
- DAP000996
- PharmGKB
- PA450433
- PDBe Ligand
- 8MO
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Methoxsalen
- PDB Entries
- 1z11
- FDA label
- Download (240 KB)
- MSDS
- Download (77.6 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 Completed Treatment Human Immunodeficiency Virus (HIV) Infections 1 somestatus stop reason just information to hide Not Available Recruiting Not Available Sezary Syndrome 1 somestatus stop reason just information to hide 4 Completed Treatment Cutaneous T-Cell Lymphoma (CTCL) / Mycosis Fungoides (MF) 1 somestatus stop reason just information to hide 4 Terminated Treatment Cutaneous T-Cell Lymphoma (Mycosis Fungoides) 1 somestatus stop reason just information to hide 3 Completed Treatment Patch/Plaque Stage Mycosis Fungoides 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Valeant pharmaceuticals international
- Sandoz inc
- Therakos inc
- Packagers
- Ben Venue Laboratories Inc.
- Catalent Pharma Solutions
- Legacy Pharmaceuticals Packaging LLC
- Pharmaceutical Utilization Management Program VA Inc.
- Spectrum Pharmaceuticals
- Therakos Inc.
- Valeant Ltd.
- Dosage Forms
Form Route Strength Capsule, gelatin coated Oral 10 mg/1 Tablet, coated Oral 500 mg Ointment Cutaneous 0.40 g Tablet Oral 10.000 mg Tablet Oral 10 mg Capsule, liquid filled Oral 10 mg/1 Lotion Topical 1 g Tablet, coated Oral 10 mg Lotion Topical 10 mg/1mL Capsule Oral Solution Extracorporeal Lotion Topical 10 mg / mL Capsule Oral 10 mg Solution Topical 1 % Liquid Topical 1 % Injection, solution Extracorporeal 20 ug/1mL Solution Solution Extracorporeal 20 mcg / mL Solution 20 mg/ml Gel Topical 0.1 % Gel Topical 1 % - Prices
Unit description Cost Unit Methoxsalen crystal 242.2USD g 8-mop 10 mg capsule 35.4USD capsule Oxsoralen-ultra 10 mg capsule 35.4USD capsule Oxsoralen 1% lotion 18.86USD ml Oxsoralen Ultra 10 mg Capsule 18.65USD capsule Uvadex 20 mcg/ml vial 9.5USD ml Oxsoralen 10 mg/ml Lotion 1.65USD g Oxsoralen 10 mg Capsule 0.65USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 148 °C PhysProp water solubility 47.6 mg/L (at 30 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 1.7 Not Available logS -3.66 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.164 mg/mL ALOGPS logP 2.1 ALOGPS logP 1.78 Chemaxon logS -3.1 ALOGPS pKa (Strongest Basic) -2.9 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 48.67 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 56.85 m3·mol-1 Chemaxon Polarizability 20.98 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9921 Blood Brain Barrier + 0.9211 Caco-2 permeable + 0.6185 P-glycoprotein substrate Non-substrate 0.5518 P-glycoprotein inhibitor I Inhibitor 0.5 P-glycoprotein inhibitor II Inhibitor 0.5468 Renal organic cation transporter Non-inhibitor 0.8178 CYP450 2C9 substrate Non-substrate 0.7921 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.6236 CYP450 1A2 substrate Inhibitor 0.9629 CYP450 2C9 inhibitor Non-inhibitor 0.5968 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Inhibitor 0.9316 CYP450 3A4 inhibitor Inhibitor 0.774 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7381 Ames test AMES toxic 0.886 Carcinogenicity Non-carcinogens 0.9552 Biodegradation Not ready biodegradable 0.7255 Rat acute toxicity 2.4054 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9563 hERG inhibition (predictor II) Non-inhibitor 0.9638
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 148.1966756 predictedDarkChem Lite v0.1.0 [M-H]- 142.5211226 predictedDarkChem Lite v0.1.0 [M-H]- 149.9333756 predictedDarkChem Lite v0.1.0 [M-H]- 149.7399756 predictedDarkChem Lite v0.1.0 [M-H]- 142.88535 predictedDeepCCS 1.0 (2019) [M+H]+ 148.8630756 predictedDarkChem Lite v0.1.0 [M+H]+ 150.5244756 predictedDarkChem Lite v0.1.0 [M+H]+ 150.6932756 predictedDarkChem Lite v0.1.0 [M+H]+ 150.8766756 predictedDarkChem Lite v0.1.0 [M+H]+ 145.26976 predictedDeepCCS 1.0 (2019) [M+Na]+ 149.2456756 predictedDarkChem Lite v0.1.0 [M+Na]+ 154.7443835 predictedDarkChem Lite v0.1.0 [M+Na]+ 150.5500756 predictedDarkChem Lite v0.1.0 [M+Na]+ 151.44548 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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Yes
Intercalation
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Smith SI, Brodbelt JS: Rapid characterization of cross-links, mono-adducts, and non-covalent binding of psoralens to deoxyoligonucleotides by LC-UV/ESI-MS and IRMPD mass spectrometry. Analyst. 2010 May;135(5):943-52. doi: 10.1039/b924023c. Epub 2010 Feb 12. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Binder
- General Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56517.005 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Enzymes
- 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
- Tassaneeyakul W, Birkett DJ, Veronese ME, McManus ME, Tukey RH, Quattrochi LC, Gelboin HV, Miners JO: Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. J Pharmacol Exp Ther. 1993 Apr;265(1):401-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Exhibits a coumarin 7-hydroxylase activity. Active in the metabolic activation of hexamethylphosphoramide, N,N-dimethylaniline, 2'-methoxyacetophenone, N-nitrosomethylphenylamine, and the tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Possesses phenacetin O-deethylation activity
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2A13
- Uniprot ID
- Q16696
- Uniprot Name
- Cytochrome P450 2A13
- Molecular Weight
- 56687.095 Da
References
- von Weymarn LB, Zhang QY, Ding X, Hollenberg PF: Effects of 8-methoxypsoralen on cytochrome P450 2A13. Carcinogenesis. 2005 Mar;26(3):621-9. doi: 10.1093/carcin/bgh348. Epub 2004 Dec 3. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity
- Specific Function
- arachidonic acid epoxygenase activity
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56517.005 Da
References
- Zhang W, Kilicarslan T, Tyndale RF, Sellers EM: Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro. Drug Metab Dispos. 2001 Jun;29(6):897-902. [Article]
- Takeuchi H, Saoo K, Yokohira M, Ikeda M, Maeta H, Miyazaki M, Yamazaki H, Kamataki T, Imaida K: Pretreatment with 8-methoxypsoralen, a potent human CYP2A6 inhibitor, strongly inhibits lung tumorigenesis induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in female A/J mice. Cancer Res. 2003 Nov 15;63(22):7581-3. [Article]
- Bagdas D, Muldoon PP, Zhu AZ, Tyndale RF, Damaj MI: Effects of methoxsalen, a CYP2A5/6 inhibitor, on nicotine dependence behaviors in mice. Neuropharmacology. 2014 Oct;85:67-72. doi: 10.1016/j.neuropharm.2014.05.006. Epub 2014 May 21. [Article]
- Raunio H, Rautio A, Gullsten H, Pelkonen O: Polymorphisms of CYP2A6 and its practical consequences. Br J Clin Pharmacol. 2001 Oct;52(4):357-63. [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: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
- Zhang W, Kilicarslan T, Tyndale RF, Sellers EM: Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro. Drug Metab Dispos. 2001 Jun;29(6):897-902. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 15, 2024 05:47