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Identification
NameMethoxsalen
Accession NumberDB00553  (APRD00157)
TypeSmall Molecule
GroupsApproved
Description

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. [PubChem]

Structure
Thumb
Synonyms
6-Hydroxy-7-methoxy-5-benzofuranacrylic acid delta-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
Meladinine
Meloxine
Methoxalen
Methoxsalen
Méthoxsalène
O-Methylxanthotoxol
Oxsoralen
Ultra mop
Uvadex
Xanthotoxin
Xanthotoxine
Xanthoxin
Zanthotoxin
External Identifiers
  • 8-MOP
  • 9-Methoxypsoralen
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
8-mopcapsule, gelatin coated10 mg/1oralValeant Pharmaceuticals North America LLC1954-12-03Not applicableUs
Methoxsalencapsule, liquid filled10 mg/1oralOceanside Pharmaceuticals2014-07-15Not applicableUs
Oxsoralenlotion10 mg/mLtopicalValeant Pharmaceuticals North America LLC1954-12-03Not applicableUs
Oxsoralen Cap 10mgcapsule10 mgoralValeant Canada Lp Valeant Canada S.E.C.1992-12-312015-08-05Canada
Oxsoralen Lot 10mg/mllotion10 mgtopicalValeant Canada Lp Valeant Canada S.E.C.1992-12-312015-08-05Canada
Oxsoralen-ultracapsule, liquid filled10 mg/1oralValeant Pharmaceuticals North America LLC1986-10-30Not applicableUs
Oxsoralen-ultra Cap 10mgcapsule10 mgoralValeant Canada Lp Valeant Canada S.E.C.1991-12-312015-08-05Canada
Ultra Mop Lotion 1%liquid1 %topicalCanderm G.P.1986-12-312008-08-06Canada
Ultramop Cap 10mgcapsule10 mgoralCanderm G.P.1985-12-312011-07-28Canada
Uvadexsolution20 mcgextracorporealTherakos Inc2013-12-09Not applicableCanada
Uvadexinjection, solution20 ug/mLextracorporealTherakos, Inc.1999-02-25Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Methoxsalencapsule, liquid filled10 mg/1oralActavis Pharma, Inc.2015-08-15Not applicableUs
Methoxsalencapsule, liquid filled10 mg/1oralStrides Arcolab Limited2014-06-13Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
DeltasoralenDelta
MeladinineCLS Pharma
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIU4VJ29L7BQ
CAS number298-81-7
WeightAverage: 216.1895
Monoisotopic: 216.042258744
Chemical FormulaC12H8O4
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct Parent8-methoxypsoralens
Alternative Parents
Substituents
  • 8-methoxypsoralen
  • 1-benzopyran
  • Benzopyran
  • Benzofuran
  • Anisole
  • Pyranone
  • Alkyl aryl ether
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Furan
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of psoriasis and vitiligo
PharmacodynamicsMethoxsalen 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 actionAfter activation it binds preferentially to the guanine and cytosine moieties of DNA, leading to cross-linking of DNA, thus inhibiting DNA synthesis and function.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationIn 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 lifeApproximately 2 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9921
Blood Brain Barrier+0.9211
Caco-2 permeable+0.6185
P-glycoprotein substrateNon-substrate0.5518
P-glycoprotein inhibitor IInhibitor0.5
P-glycoprotein inhibitor IIInhibitor0.5468
Renal organic cation transporterNon-inhibitor0.8178
CYP450 2C9 substrateNon-substrate0.7921
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6236
CYP450 1A2 substrateInhibitor0.9629
CYP450 2C9 inhibitorNon-inhibitor0.5968
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.9316
CYP450 3A4 inhibitorInhibitor0.774
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7381
Ames testAMES toxic0.886
CarcinogenicityNon-carcinogens0.9552
BiodegradationNot ready biodegradable0.7255
Rat acute toxicity2.4054 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9563
hERG inhibition (predictor II)Non-inhibitor0.9638
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Valeant pharmaceuticals international
  • Sandoz inc
  • Therakos inc
Packagers
Dosage forms
FormRouteStrength
Capsule, gelatin coatedoral10 mg/1
Lotiontopical10 mg/mL
Lotiontopical10 mg
Capsule, liquid filledoral10 mg/1
Capsuleoral10 mg
Liquidtopical1 %
Injection, solutionextracorporeal20 ug/mL
Solutionextracorporeal20 mcg
Prices
Unit descriptionCostUnit
Methoxsalen crystal242.2USD g
8-mop 10 mg capsule35.4USD capsule
Oxsoralen-ultra 10 mg capsule35.4USD capsule
Oxsoralen 1% lotion18.86USD ml
Oxsoralen Ultra 10 mg Capsule18.65USD capsule
Uvadex 20 mcg/ml vial9.5USD ml
Oxsoralen 10 mg/ml Lotion1.65USD g
Oxsoralen 10 mg Capsule0.65USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point148 °CPhysProp
water solubility47.6 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP1.7Not Available
logS-3.66ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.164 mg/mLALOGPS
logP2.1ALOGPS
logP1.78ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48.67 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity56.85 m3·mol-1ChemAxon
Polarizability20.98 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-4767833559e7bd183ce0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-c471bf567e8a63e00e51View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bi-0930000000-72a72a3eb013e045bdb0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0290000000-c9557f276875a3bf1d2bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0390000000-ff927b8db6ef70ef822dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0910000000-d2e511be224be1b3530eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-014i-9670000000-3e0fa2e9c81c3bc1d936View in MoNA
1D NMR1H NMR SpectrumNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesD05AD02D05BA02
AHFS Codes
  • 84:50.06
PDB EntriesNot Available
FDA labelDownload (240 KB)
MSDSDownload (77.6 KB)
Interactions
Drug Interactions
Drug
AgomelatineThe serum concentration of Agomelatine can be increased when it is combined with Methoxsalen.
AripiprazoleThe serum concentration of Aripiprazole can be increased when it is combined with Methoxsalen.
ArtesunateThe serum concentration of the active metabolites of Artesunate can be reduced when Artesunate is used in combination with Methoxsalen resulting in a loss in efficacy.
BendamustineThe serum concentration of Bendamustine can be increased when it is combined with Methoxsalen.
BortezomibThe metabolism of Bortezomib can be decreased when combined with Methoxsalen.
ClozapineThe serum concentration of Clozapine can be increased when it is combined with Methoxsalen.
DuloxetineThe serum concentration of Duloxetine can be increased when it is combined with Methoxsalen.
FluvoxamineThe metabolism of Fluvoxamine can be decreased when combined with Methoxsalen.
NicotineThe metabolism of Nicotine can be decreased when combined with Methoxsalen.
PentoxifyllineThe serum concentration of Pentoxifylline can be increased when it is combined with Methoxsalen.
PirfenidoneThe serum concentration of Pirfenidone can be increased when it is combined with Methoxsalen.
PomalidomideThe serum concentration of Pomalidomide can be increased when it is combined with Methoxsalen.
PorfimerMethoxsalen may increase the photosensitizing activities of Porfimer.
RasagilineThe serum concentration of Rasagiline can be increased when it is combined with Methoxsalen.
TasimelteonThe serum concentration of Tasimelteon can be increased when it is combined with Methoxsalen.
TegafurThe serum concentration of the active metabolites of Tegafur can be reduced when Tegafur is used in combination with Methoxsalen resulting in a loss in efficacy.
TizanidineThe serum concentration of Tizanidine can be increased when it is combined with Methoxsalen.
VerteporfinMethoxsalen may increase the photosensitizing activities of Verteporfin.
Food Interactions
  • Take with food or milk, or in two divided doses 30 minutes apart to decrease nausea.

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
yes
Actions
intercalation
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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. [PubMed:17016423 ]
  3. 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. [PubMed:20419242 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific 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.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular Weight:
56501.005 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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 unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific 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.
Gene Name:
CYP2A13
Uniprot ID:
Q16696
Molecular Weight:
56687.095 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Vitamin d3 25-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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11