DT-Web

DB04571 - Trioxsalen


Identification
Name Trioxsalen
Accession Number DB04571
Type small molecule
Description Trioxsalen (trimethylpsoralen, trioxysalen or trisoralen) is a furanocoumarin and a psoralen derivative. It is obtained from several plants, mainly Psoralea corylifolia. Like other psoralens it causes photosensitization of the skin. It is administered either topically or orally in conjunction with UV-A (the least damaging form of ultraviolet light) for phototherapy treatment of vitiligo[1] and hand eczema.[2] After photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death unless repaired by cellular mechanisms. In research it can be conjugated to dyes for confocal microscopy and used to visualize sites of DNA damage.[3] The compound is also being explored for development of antisense oligonucleotides that can be cross-linked specifically to a mutant mRNA sequence without affecting normal transcripts differing at even a single base pair.
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 228.2433
Groups approved
Monoisotopic Weight 228.07864425
Pharmacology
Indication Trioxsalen is a pigmenting photosensitizing agent used in conjunction with ultraviolet light in the treatment of vitiligo.
Mechanism of action After photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death.
Absorption Not Available
Protein binding Not Available
Biotransformation Not Available
Route of elimination Not Available
Toxicity Not Available
Affected organisms Not Available
Interactions
Drug Interactions
Drug Mechanism of interaction
Fosphenytoin The hydantoin decreases the effect of psoralene
Phenytoin The hydantoin decreases the effect of psoralene
Food Interactions
  • avoid eating limes, figs, parsley, parsnips, mustard, carrots, and celery while you are being treated with trioxsalen

Targets


DNA
Name DNA
Gene Name Not Available
Pharmacological action yes
Actions cross-linking/alkylation
References
  • Thazhathveetil AK, Liu ST, Indig FE, Seidman MM: Psoralen conjugates for visualization of genomic interstrand cross-links localized by laser photoactivation. Bioconjug Chem. 2007 Mar-Apr;18(2):431-7. - Pubmed
  • Vasquez KM, Wensel TG, Hogan ME, Wilson JH: High-efficiency triple-helix-mediated photo-cross-linking at a targeted site within a selectable mammalian gene. Biochemistry. 1996 Aug 20;35(33):10712-9. - Pubmed
  • Dardare N, Platz MS: Binding affinities of commonly employed sensitizers of viral inactivation. Photochem Photobiol. 2002 Jun;75(6):561-4. - Pubmed
  • Jimenez-Ruiz A, Zhang Q, Shen CK: In vivo binding of trimethylpsoralen detects DNA structural alterations associated with transcribing regions in the human beta-globin cluster. J Biol Chem. 1995 Dec 1;270(48):28978-81. - Pubmed
DTHybrid score Not Available

Predictions


Id Partner name Gene Name Score
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