Drugbank Logo

Showing drug card for Methoxsalen (DB00553)

Legend: drug field target field enzyme field

for drugs
Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-04-16 16:47:47
Primary Accession Number DB00553
Secondary Accession Number
  • APRD00157
Name Methoxsalen
Drug Type
  • Approved
  • Small Molecule
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]
Synonyms Not Available
Brand Names
  1. Ammodin
  2. Ammoidin
  3. Meladinin
  4. Meladinine
  5. Meladoxen
  6. Meloxine
  7. Methoxa-Dome
  8. Methoxalen
  9. Methoxaten
  10. New-Meladinin
  11. Oxoralen
  12. Oxsoralen
  13. Oxsoralen Lotion
  14. Oxsoralen-Ultra
  15. Oxypsoralen
  16. Proralone-Mop
  17. Psoralen-Mop
  18. Puvalen
  19. Puvamet
  20. Ultra Mop
  21. Ultramop Lotion
  22. Uvadex
  23. Xanthotoxin
  24. Xanthotoxine
  25. Xanthoxin
  26. Zanthotoxin
Brand Mixtures Not Available
Chemical IUPAC Name 9-methoxyfuro[3,2-g]chromen-7-one
Chemical Formula C12H8O4
Chemical Structure Structure
CAS Registry Number 298-81-7
InChI Identifier InChI=1/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3
InChI Key QXKHYNVANLEOEG-UHFFFAOYAV
KEGG Drug D00139 Link Image
KEGG Compound C01864 Link Image
PubChem Compound 4114 Link Image
PubChem Substance 152480 Link Image
ChEBI ID 18358 Link Image
PharmGKB ID Not Available
HET ID 8MO Link Image
GenBank ID Not Available
Drug ID Number [DIN] 00698059 Link Image
RxList Link http://www.rxlist.com/cgi/generic2/methox.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Methoxsalen Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 216.1895
Monoisotopic Molecular Weight 216.0423
State Solid
Melting Point Not Available
Experimental Water Solubility 0.0476 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 1.64e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 1.7 Source: PhysProp
Predicted LogP 2.10 Calculated using ALOGPS
Experimental LogS -3.66 [ADME Research, USCD]
Predicted LogS -3.12 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES COC1=C2OC(=O)C=CC2=CC2=C1OC=C2
Canonical SMILES COC1=C2OC(=O)C=CC2=CC2=C1OC=C2
Drug Category
  • Antineoplastic Agents
  • Cross-Linking Reagents
  • Photosensitizing Agents
  • Pigmenting Agents
ATC Codes
AHFS Codes
  • 84:50.06
Indication For the treatment of psoriasis and vitiligo
Pharmacology 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.
Absorption Not Available
Toxicity Not Available
Protein Binding Not Available
Biotransformation Not Available
Half Life Approximately 2 hours
Dosage Forms
Form Route
Capsule Oral
Liquid Topical
Lotion Topical
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Ethotoin The hydantoin decreases the effect of psoralene
Fosphenytoin The hydantoin decreases the effect of psoralene
Mephenytoin The hydantoin decreases the effect of psoralene
Phenytoin The hydantoin decreases the effect of psoralene
Food Interactions
  • Take with food or milk, or in two divided doses 30 minutes apart to decrease nausea.
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Humans and other mammals
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 2A6 (CYP2A6)
Targets
  1. DNA
  2. Cytochrome P450 2A6
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 2A6 (CYP2A6)
Enzyme 1 Gene Name CYP2A6
Enzyme 1 SwissProt ID P11509 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P11509|CP2A6_HUMAN Cytochrome P450 2A6 (EC 1.14.14.1) 
MLASGMLLVALLVCLTVMVLMSVWQQRKSKGKLPPGPTPLPFIGNYLQLNTEQMYNSLMK
ISERYGPVFTIHLGPRRVVVLCGHDAVREALVDQAEEFSGRGEQATFDWVFKGYGVVFSN
GERAKQLRRFSIATLRDFGVGKRGIEERIQEEAGFLIDAHRGTGGANIDPTFFLSRTVSN
VISSIVFGDRFDYKDKEFLSLLRMMLGIFQFTSTSTGQLYEMFSSVMKHLPGPQQQAFQL
LQGLEDFIAKKVEHNQRTLDPNSPRDFIDSFLIRMQEEEKNPNTEFYLKNLVMTTLNLFI
GGTETVSTTLRYGFLLLMKHPEVEAKVHEEIDRVIGKNRQPKFEDRAKMPYMEAVIHEIQ
RFGDVIPMSLARRVKKDTKFRDFFLPKGTEVYPMLGSVLRDPSFFSNPQDFNPQHFLNEK
GQFKKSDAFVPFSIGKRNCFGEGLARMELFLFFTTVMQNFRLKSSQSPKDIDVSPKHVGF
ATIPRNYTMSFLPR
Drug Target 1 [top]
Target 1 ID 874
Target 1 Name DNA
Target 1 Synonyms
  1. Deoxyribonucleic acid
Target 1 Gene Name Not Available
Target 1 Protein Sequence Not Available
Target 1 Number of Residues 0
Target 1 Molecular Weight 7656 (double strand)
Target 1 Theoretical pI Not Available
Target 1 GO Classification
Function
information storage
information transfer
Process
DNA replication and chromosomal cycle
DNA replication
DNA-dependent DNA replication
DNA replication, synthesis of RNA primer
transcription
transcription, DNA dependent
Component
cell
intracellular
nucleus
mitochondria
Target 1 General Function Biological information storage and information transfer
Target 1 Specific Function 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.
Target 1 Pathways
Name SMPDB Link KEGG Link
DNA polymerase map03030 Link Image
RNA polymerase map03020 Link Image
Target 1 Reactions
  • DNA + DNA polymerase + nNTP = 2 DNA + nNDP; DNA + RNA polymerase + NTP = mRNA + nNDP
Target 1 Pfam Domain Function Not Available
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB/Swiss-Prot ID Not Available
Target 1 UniProtKB/Swiss-Prot Entry Name Not Available
Target 1 PDB ID 1BNA Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Nucleus and mitochondria
Target 1 Gene Sequence >Example: Dickerson dodecamer 
CGCGAATTCGCG
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus All loci
Target 1 SNPs Not Available
Target 1 General References
  1. Nadeau D, Marchand C: Change in the kinetics of sulphacetamide tissue distribution in Walker tumor-bearing rats. Drug Metab Dispos. 1975 Nov-Dec;3(6):565-76. [PubMed Link Image]
Target 1 Drug References
  1. 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 Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
Drug Target 2 [top]
Target 2 ID 5718
Target 2 Name Cytochrome P450 2A6
Target 2 Synonyms
  1. CYP2A3
  2. CYPIIA6
  3. Coumarin 7-hydroxylase
  4. EC 1.14.14.1
  5. P450 IIA3
  6. P450(I)
Target 2 Gene Name CYP2A6
Target 2 Protein Sequence >Cytochrome P450 2A6 
MLASGMLLVALLVCLTVMVLMSVWQQRKSKGKLPPGPTPLPFIGNYLQLNTEQMYNSLMK
ISERYGPVFTIHLGPRRVVVLCGHDAVREALVDQAEEFSGRGEQATFDWVFKGYGVVFSN
GERAKQLRRFSIATLRDFGVGKRGIEERIQEEAGFLIDAHRGTGGANIDPTFFLSRTVSN
VISSIVFGDRFDYKDKEFLSLLRMMLGIFQFTSTSTGQLYEMFSSVMKHLPGPQQQAFQL
LQGLEDFIAKKVEHNQRTLDPNSPRDFIDSFLIRMQEEEKNPNTEFYLKNLVMTTLNLFI
GGTETVSTTLRYGFLLLMKHPEVEAKVHEEIDRVIGKNRQPKFEDRAKMPYMEAVIHEIQ
RFGDVIPMSLARRVKKDTKFRDFFLPKGTEVYPMLGSVLRDPSFFSNPQDFNPQHFLNEK
GQFKKSDAFVPFSIGKRNCFGEGLARMELFLFFTTVMQNFRLKSSQSPKDIDVSPKHVGF
ATIPRNYTMSFLPR
Target 2 Number of Residues 502
Target 2 Molecular Weight 56542
Target 2 Theoretical pI 9.69
Target 2 GO Classification
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
tetrapyrrole binding
heme binding
binding
ion binding
cation binding
transition metal ion binding
iron ion binding
catalytic activity
oxidoreductase activity
monooxygenase activity
Process
physiological process
metabolism
cellular metabolism
generation of precursor metabolites and energy
electron transport
Component
Not Available
Target 2 General Function Involved in monooxygenase activity
Target 2 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
Target 2 Pathways Not Available
Target 2 Reactions Not Available
Target 2 Pfam Domain Function
Target 2 Signals
  • None
Target 2 Transmembrane Regions
  • None
Target 2 Essentiality Non Essential
Target 2 GenBank ID Protein Not Available
Target 2 UniProtKB/Swiss-Prot ID P11509 Link Image
Target 2 UniProtKB/Swiss-Prot Entry Name CP2A6_HUMAN Link Image
Target 2 PDB ID Not Available
Target 2 Cellular Location
  • Endoplasmic reticulum
Target 2 Gene Sequence >1470 bp 
ATGCTTCTGGTGGCCTTGCTGGTCTGCCTGACTGTAATGGTCTTGATGTCTGTTTGGCAG
CAGAGGAAGAACAAGGGGAAGCTGCCTCCGGGACCCACCCCATTGCCCTTCATTGGAAAC
TACCTGCAGCTGAACACAGAGCAGATGTACAACTCCCTCATGAAGATCAGTGAGCGCTAT
GGCCCCGTGTTCACCATTCACTTGGGGCCCCGGCGGGTCGTGGTGCTGTGTGGACATGAT
GCCGTCAGGGAGGCTCTGGTGGACCAGGCTGAGGAGTTCAGCGGGCGAGGCGAGCAAGCC
ACCTTCGACTGGGTCTTCAAAGGCTATGGCGTGGTATTCAGCAACGGGGAGCGCGCCAAG
CAGCTCCGGCGCTTCTCCATCGCCACCCTGCGGGACTTCGGGGTGGGCAAGCGAGGCATC
GAGGAGCGCATCCAGGAGGAGGCGGGCTTCCTCATCGACGCCCTCCGGGGCACTGGCGGC
GCCAATATCGATCCCACCTTCTTCCTGAGCCGCACAGTCTCCAATGTCATCAGCTCCATT
GTCTTTGGGGACCGCTTTGACTATAAGGACAAAGAGTTCCTGTCACTGTTGCGCATGATG
CTAGGAATCTTCCAGTTCACGTCAACCTCCACGGGGCAGCTCTATGAGATGTTCTCTTCG
GTGATGAAACACCTGCCAGGACCACAGCAACAGGCCTTTCAGTTGCTGCAAGGGCTGGAG
GACTTCATAGCCAAGAAGGTGGAGCACAAACAGCGCACGCTGGATCCCAATTCCCCACGG
GACTTCATTGACTCCTTTCTCATCCGCATGCAGGAGGAGGAGAAGAACCCCAACACGGAG
TTCTACTTGAAAAACCTGGTGATGACCACGTTGAACCTCTTCATTGGGGGCACCGAGACC
GTCAGCACCACCCTGCGCTATGGCTTCTTGCTGCTCATGAAGCACCCAGAGGTGGAGGCC
CAGGTCCATGAGGAGATTGACAGAGTGATCGGCAAGAACCGGCAGCCCAAGTTTGAGGAC
CGGGCCAAGATGCCCTACATGGAGGCAGTGATCCACGAGATCCAAAGATTTGGAGACGTG
ATCCCCATGAGTTTGGCCCGCAGAGTCAAAAAGGACACCAAGTTTCGGGATTTCTTCCTC
CCTAAGGGCACCGAAGTGTACCCTATGCTGGGCTCTGTGCTGAGAGACCCCAGTTTCTTC
TCCAACCCCCAGGACTTCAATCCCCAGCACTTCCTGAATGAGAAGGGGCAGTTTAAGAAG
AGTGATGCTTTTGTGCCCTTTTCCATCGGAAAGCGGAACTGTTTCGGAGAAGGCCTGGCC
AGAATGGAGCTCTTTCTCTTCTTCACCACCGTCATGCAGAACTTCCGCCTCAAGTCCTCC
CAGTCACCTAAGGACATTGACGTGTCCCCCAAACACGTGGGCTTTGCCACGATCCCACGA
AACTACACCATGAGCTTCCTGCCCCGCTGA
Target 2 GenBank Gene ID
Target 2 GeneCard ID Not Available
Target 2 GenAtlas ID CYP2A6 Link Image
Target 2 HGNC ID HGNC:2610 Link Image
Target 2 Chromosome Location 19
Target 2 Locus 19q13.2
Target 2 SNPs SNPJam Report Link Image
Target 2 General References
  1. Kitagawa K, Kunugita N, Kitagawa M, Kawamoto T: CYP2A6*6, a novel polymorphism in cytochrome p450 2A6, has a single amino acid substitution (R128Q) that inactivates enzymatic activity. J Biol Chem. 2001 May 25;276(21):17830-5. Epub 2001 Feb 16. [PubMed Link Image]
  2. Yun CH, Shimada T, Guengerich FP: Purification and characterization of human liver microsomal cytochrome P-450 2A6. Mol Pharmacol. 1991 Nov;40(5):679-85. [PubMed Link Image]
  3. Yamano S, Tatsuno J, Gonzalez FJ: The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes. Biochemistry. 1990 Feb 6;29(5):1322-9. [PubMed Link Image]
  4. Miles JS, Bickmore W, Brook JD, McLaren AW, Meehan R, Wolf CR: Close linkage of the human cytochrome P450IIA and P450IIB gene subfamilies: implications for the assignment of substrate specificity. Nucleic Acids Res. 1989 Apr 25;17(8):2907-17. [PubMed Link Image]
  5. Yamano S, Nagata K, Yamazoe Y, Kato R, Gelboin HV, Gonzalez FJ: cDNA and deduced amino acid sequences of human P450 IIA3 (CYP2A3). Nucleic Acids Res. 1989 Jun 26;17(12):4888. [PubMed Link Image]
  6. Phillips IR, Shephard EA, Ashworth A, Rabin BR: Isolation and sequence of a human cytochrome P-450 cDNA clone. Proc Natl Acad Sci U S A. 1985 Feb;82(4):983-7. [PubMed Link Image]
Target 2 Drug References Not Available

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.