Banner
targets (1)
for drugs
Identification
Name Trioxsalen
Accession Number DB04571
Type small molecule
Groups approved
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 vitiligo1 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 Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
trimethylpsoralen
trioxysalen
trisoralen
Salts Not Available
Brand names Not Available
Brand mixtures Not Available
Categories
  • Photosensitizing Agents
CAS number 3902-71-4
Weight Average: 228.2433
Monoisotopic: 228.07864425
Chemical Formula C14H12O3
InChI Key InChIKey=FMHHVULEAZTJMA-UHFFFAOYSA-N
InChI
InChI=1S/C14H12O3/c1-7-4-12(15)17-14-9(3)13-10(6-11(7)14)5-8(2)16-13/h4-6H,1-3H3
Plain Text
IUPAC Name
4,7,9-trimethyl-2H-furo[3,2-g]chromen-2-one
SMILES
CC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O1
Plain Text
Mass Spec show (8.79 KB)
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Trioxsalen is a pigmenting photosensitizing agent used in conjunction with ultraviolet light in the treatment of vitiligo.
Pharmacodynamics Trioxsalen ispharmacologically inactive but when exposed to ultraviolet radiation or sunlight it is converted to its active metabolite to produce a beneficial reaction affecting the diseased tissue.
Mechanism of action After photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms Not Available
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Valeant pharmaceuticals international
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 234.5 °C PhysProp
Predicted Properties
Property Value Source
water solubility 6.27e-02 g/l ALOGPS
logP 3.26 ALOGPS
logP 2.95 ChemAxon
logS -3.6 ALOGPS
pKa (strongest basic) -2.7 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 39.44 ChemAxon
rotatable bond count 0 ChemAxon
refractivity 64.86 ChemAxon
polarizability 24.77 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. van Coevorden AM, Kamphof WG, van Sonderen E, Bruynzeel DP, Coenraads PJ: Comparison of oral psoralen-UV-A with a portable tanning unit at home vs hospital-administered bath psoralen-UV-A in patients with chronic hand eczema: an open-label randomized controlled trial of efficacy. Arch Dermatol. 2004 Dec;140(12):1463-6. Pubmed
  2. 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
  3. Higuchi M, Yamayoshi A, Kobori A, Yamaoka T, Murakami A: Synthesis and properties of photo-reactive antisense oligonucleotides containing 2’-O-psoralen-conjugated adenosine. Nucleic Acids Symp Ser (Oxf). 2005;(49):331-2. Pubmed
External Links
Resource Link
KEGG Drug D01034 Link_out
KEGG Compound C09314 Link_out
PharmGKB PA164747186 Link_out
Drugs.com http://www.drugs.com/cons/trioxsalen.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Trioxsalen Link_out
ATC Codes
  • D05AD01
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug 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

1. DNA

Pharmacological action: yes
Actions: cross-linking/alkylation

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.

Gene Sequence: FASTA

References:
  1. 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
  2. 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
  3. Dardare N, Platz MS: Binding affinities of commonly employed sensitizers of viral inactivation. Photochem Photobiol. 2002 Jun;75(6):561-4. Pubmed
  4. 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
Comments
Drug created on September 07, 2007 14:54 / Updated on February 08, 2013 16:23