Methoxsalen

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
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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofCutaneous t-cell lymphoma (ctcl)•••••••••••••••••••••• ••••••••••••
Symptomatic treatment ofRefractory cutaneous t-cell lymphoma•••••••••••••••••••••• ••••••••
Treatment ofVitiligo••• ••••••••• ••••••••
Symptomatic treatment ofIdiopathic vitiligo••••••••••••
Management ofSevere psoriasis••••••••••••
Contraindications & Blackbox Warnings
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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
Humans
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
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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.
DrugInteraction
AbacavirMethoxsalen may decrease the excretion rate of Abacavir which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Methoxsalen which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Methoxsalen which could result in a higher serum level.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Methoxsalen.
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Methoxsalen.
Food Interactions
  • Take with food. Take this medication with food or milk.

Products

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Product Images
International/Other Brands
Deltasoralen (Delta) / Meladinine (CLS Pharma) / Meloxine / Ultra Mop
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
8-mopCapsule, gelatin coated10 mg/1OralValeant Pharmaceuticals North America1954-12-032017-08-31US flag
OxsoralenLotion10 mg/1mLTopicalValeant Pharmaceuticals North America1954-12-032016-06-30US flag
Oxsoralen Cap 10mgCapsule10 mgOralValeant Canada Lp Valeant Canada S.E.C.1992-12-312015-08-05Canada flag
Oxsoralen Lot 10mg/mlLotion10 mg / mLTopicalValeant Canada Lp Valeant Canada S.E.C.1992-12-312015-08-05Canada flag
Oxsoralen-UltraCapsule, liquid filled10 mg/1OralBausch Health US, LLC1986-10-30Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MethoxsalenCapsule, liquid filled10 mg/1OralStrides Pharma Science Limited2016-12-08Not applicableUS flag
MethoxsalenCapsule, liquid filled10 mg/1OralOceanside Pharmaceuticals2014-07-15Not applicableUS flag
MethoxsalenCapsule, liquid filled10 mg/1OralActavis Pharma, Inc.2016-09-14Not applicableUS flag

Categories

ATC Codes
D05BA02 — MethoxsalenD05AD02 — Methoxsalen
Drug Categories
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
Human Metabolome Database
HMDB0014693
KEGG Drug
D00139
KEGG Compound
C01864
PubChem Compound
4114
PubChem Substance
46506275
ChemSpider
3971
BindingDB
50041234
RxNav
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
PhaseStatusPurposeConditionsCount
4CompletedTreatmentCutaneous T-Cell Lymphoma (CTCL) / Mycosis Fungoides (MF)1
4TerminatedTreatmentCutaneous T-Cell Lymphoma (Mycosis Fungoides)1
3CompletedTreatmentPatch/Plaque Stage Mycosis Fungoides1
3TerminatedTreatmentAcute Graft-Versus-Host Disease (GVHD)1
3TerminatedTreatmentLymphoma1

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
Tablet, coatedOral500 mg
OintmentCutaneous0.40 g
TabletOral10.000 mg
TabletOral10 mg
Capsule, liquid filledOral10 mg/1
LotionTopical1 g
Tablet, coatedOral10 mg
LotionTopical10 mg/1mL
CapsuleOral
SolutionExtracorporeal
LotionTopical10 mg / mL
CapsuleOral10 mg
SolutionTopical
LiquidTopical1 %
Injection, solutionExtracorporeal20 ug/1mL
Solution
SolutionExtracorporeal20 mcg / mL
Solution20 mg/ml
GelTopical0.1 %
GelTopical1 %
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-MSsplash10-000i-1920000000-98f6cfda190045d0762a
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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-014i-1590000000-f70cf2b0756e8c80c17b
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-014i-0890000000-f76d6fb28854a5d7b6cd
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0fk9-0920000000-c2bd0b76c5aed757e904
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-62b602bee845ac00c322
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-6076cd8bd815f1abfe4d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-fa8ee8ed54ff81feb55d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0190000000-5a66d2832535d05bb090
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-1900000000-b91e5a5a117443aef15d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0290000000-10dca05a1c70cf9339de
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-148.1966756
predicted
DarkChem Lite v0.1.0
[M-H]-142.5211226
predicted
DarkChem Lite v0.1.0
[M-H]-149.9333756
predicted
DarkChem Lite v0.1.0
[M-H]-149.7399756
predicted
DarkChem Lite v0.1.0
[M-H]-142.88535
predicted
DeepCCS 1.0 (2019)
[M+H]+148.8630756
predicted
DarkChem Lite v0.1.0
[M+H]+150.5244756
predicted
DarkChem Lite v0.1.0
[M+H]+150.6932756
predicted
DarkChem Lite v0.1.0
[M+H]+150.8766756
predicted
DarkChem Lite v0.1.0
[M+H]+145.26976
predicted
DeepCCS 1.0 (2019)
[M+Na]+149.2456756
predicted
DarkChem Lite v0.1.0
[M+Na]+154.7443835
predicted
DarkChem Lite v0.1.0
[M+Na]+150.5500756
predicted
DarkChem Lite v0.1.0
[M+Na]+151.44548
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Nucleotide
Organism
Humans
Pharmacological action
Yes
Actions
Intercalation
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
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. 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
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. 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
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. 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]
  2. 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]
  3. 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]
  4. 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
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. 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 March 19, 2024 11:06