Identification

Name
Methoxsalen
Accession Number
DB00553  (APRD00157)
Type
Small Molecule
Groups
Approved
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.

Structure
Thumb
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
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
8-mopCapsule, gelatin coated10 mg/1OralValeant Pharmaceuticals North America1954-12-032017-08-31Us
OxsoralenLotion10 mg/1mLTopicalValeant Pharmaceuticals North America1954-12-032016-06-30Us
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 America1986-10-30Not 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 mcgExtracorporealTherakos2013-12-09Not applicableCanada
UvadexInjection, solution20 ug/1mLExtracorporealTherakos1999-02-25Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MethoxsalenCapsule, liquid filled10 mg/1OralOceanside Pharmaceuticals2014-07-15Not applicableUs68682 0065 10 nlmimage10 a744d396
MethoxsalenCapsule, liquid filled10 mg/1OralActavis Pharma Company2016-09-14Not applicableUs
MethoxsalenCapsule, liquid filled10 mg/1OralStrides Shasun Limited2014-06-13Not applicableUs
International/Other Brands
Deltasoralen (Delta) / Meladinine (CLS Pharma) / Meloxine / Oxsoralen / Ultra Mop / Uvadex
Categories
UNII
U4VJ29L7BQ
CAS number
298-81-7
Weight
Average: 216.192
Monoisotopic: 216.042258738
Chemical Formula
C12H8O4
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

Pharmacology

Indication

For the treatment of psoriasis and vitiligo

Associated Conditions
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.

TargetActionsOrganism
ADNA
intercalation
Human
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Methoxsalen.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Methoxsalen.
8-azaguanineThe metabolism of 8-azaguanine can be decreased when combined with Methoxsalen.
8-chlorotheophyllineThe metabolism of 8-chlorotheophylline can be decreased when combined with Methoxsalen.
9-DeazaguanineThe metabolism of 9-Deazaguanine can be decreased when combined with Methoxsalen.
9-MethylguanineThe metabolism of 9-Methylguanine can be decreased when combined with Methoxsalen.
AbacavirMethoxsalen may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseAcarbose may decrease the excretion rate of Methoxsalen which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Methoxsalen which could result in a higher serum level.
AcefyllineThe metabolism of Acefylline can be decreased when combined with Methoxsalen.
Food Interactions
  • Take with food or milk, or in two divided doses 30 minutes apart to decrease nausea.

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
ChEBI
18358
ChEMBL
CHEMBL416
Therapeutic Targets Database
DAP000996
PharmGKB
PA450433
HET
8MO
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Methoxsalen
ATC Codes
D05AD02 — MethoxsalenD05BA02 — Methoxsalen
AHFS Codes
  • 84:50.06 — Pigmenting Agents
PDB Entries
1z11
FDA label
Download (240 KB)
MSDS
Download (77.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentChronic Graft Versus Host Disease1
1CompletedTreatmentCrohn's Disease (CD)1
1CompletedTreatmentLeukemias / Malignant Lymphomas / Multiple Myeloma and Plasma Cell Neoplasm / Myelodysplastic Syndromes1
1, 2Unknown StatusPreventionHaematological Malignancies1
2Active Not RecruitingPreventionGraft Versus Host Disease (GVHD)1
2CompletedPreventionGraft Versus Host Disease (GVHD)1
2CompletedTreatmentCrohn's Disease (CD)1
2CompletedTreatmentEpidermolysis Bullosa Acquisita1
2CompletedTreatmentGraft Versus Host Disease (GVHD)1
2CompletedTreatmentLeukemias / Myelodysplastic Syndromes / Myelodysplastic/Myeloproliferative Neoplasms1
2CompletedTreatmentRheumatoid Arthritis1
2Not Yet RecruitingTreatmentLymphoma, T-Cell, Cutaneous / Mycosis Fungoides/Sezary Syndrome1
2RecruitingTreatmentMalignant Neoplasm of Pancreas1
2SuspendedTreatmentChronic Graft Versus Host Disease / Graft Versus Host Disease (GVHD)1
2Unknown StatusTreatmentMalignant Lymphomas1
3CompletedTreatmentPatch/Plaque Stage Mycosis Fungoides1
3RecruitingTreatmentSteroid Refractory Acute Graft Versus Host Disease1
3TerminatedTreatmentAcute Graft-Versus-Host Disease1
4CompletedTreatmentCutaneous T Cell Lymphomas (CTCL) / Mycosis Fungoides (MF)1
4TerminatedTreatmentCutaneous T-Cell Lymphoma (Mycosis Fungoides)1
Not AvailableActive Not RecruitingNot AvailableBronchiolitis Obliterans Syndrome (BOS)1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1

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
FormRouteStrength
Capsule, gelatin coatedOral10 mg/1
Capsule, liquid filledOral10 mg/1
LotionTopical10 mg/1mL
LotionTopical10 mg
CapsuleOral10 mg
LiquidTopical1 %
Injection, solutionExtracorporeal20 ug/1mL
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.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)148 °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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-00ri-6940000000-921a3e8adbbde5f7a0c3
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-003b-4950000000-4e2c001531825f6dddca
Mass Spectrum (Electron Ionization)MSsplash10-014i-9670000000-3e0fa2e9c81c3bc1d936
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-4767833559e7bd183ce0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-c471bf567e8a63e00e51
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01bi-0930000000-72a72a3eb013e045bdb0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0290000000-c9557f276875a3bf1d2b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0390000000-ff927b8db6ef70ef822d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0910000000-d2e511be224be1b3530e
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0090000000-cecd035cc60695427f78
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0gb9-0290000000-2e17076c991ea61ced1a
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0uk9-0970000000-59c3b8004baa44f8d3a5
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-0190000000-cc04ec8c7265ba3a7297
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0970000000-82c4c7eefd54ad509f69
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00xs-0900000000-991b5b7dc028219e593b
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0970000000-dc6cd01d5d2e5eeaae30
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0970000000-ee8aa480dca6e72a74fb
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-0890000000-f76d6fb28854a5d7b6cd
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-1590000000-f70cf2b0756e8c80c17b
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0fk9-0920000000-c2bd0b76c5aed757e904
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0gi0-1960000000-82bc07f73bc5b2044642
MS/MS Spectrum - , positiveLC-MS/MSsplash10-014i-0690000000-770dc5d0db7e86d8ba07
1H NMR Spectrum1D NMRNot Applicable

Taxonomy

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
8-methoxypsoralen / Benzopyran / 1-benzopyran / Benzofuran / Anisole / Alkyl aryl ether / Pyranone / Pyran / Benzenoid / Furan
show 10 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
aromatic ether, psoralens (CHEBI:18358) / Polyketides, Furanocoumarins (C01864) / an 8-methoxyfurocoumarin (CPD-13042)

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
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 un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
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. 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. [PubMed:11353760]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
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]
  2. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
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 un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
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-s...
Gene Name
CYP2A13
Uniprot ID
Q16696
Uniprot Name
Cytochrome P450 2A13
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]

Drug created on June 13, 2005 07:24 / Updated on November 13, 2018 07:49