Structure via PubChem · Public domain (PubChem)
trioxsalen
Sign in to saveAlso known as 4,8,5'-Trimethylpsoralen, trimethylpsoralen, Trioxysalene, 6-Hydroxy-beta,2,7-trimethyl-5-benzofuranacrylic acid, delta-lactone, Trioxysalenum, trioxysalen, Trioxisaleno, 2',4,8-Trimethylpsoralen
Trioxsalen (trimethylpsoralen (TMP), trioxysalen (INN) 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 and hand eczema. 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 dy
In the Vinony graph
Vinony's link graph records 52 inbound references to trioxsalen, and connects out to ultraviolet radiation, mouth and genetics.
It sits within the topics ECHA InfoCard ID from Wikidata, Furanocoumarins and O-methylated coumarins.
Vinony links it to 13 Wikipedia language editions.
Chemical data
- Formula
- C14H12O3
- Molecular weight
- 228.24 g/mol
- IUPAC name
- 2,5,9-trimethylfuro[3,2-g]chromen-7-one
- SMILES
- CC1=CC(=O)OC2=C1C=C3C=C(OC3=C2C)C
- InChIKey
- FMHHVULEAZTJMA-UHFFFAOYSA-N
- XLogP
- 3
- Polar surface area
- 39.4 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1964
- Admin. routes
- oral
- Indications
- psoriasis
via ChEMBL · EBI
Wikidata facts
- Subclass of
- psoralen
- Mass
- 228.078644
- Has use
- medication
Show 7 more facts
- chemical formula
- C₁₄H₁₂O₃
- medical condition treated
- pigmentation disorder
- canonical SMILES
- CC1=CC(=O)OC2=C1C=C3C=C(OC3=C2C)C
- World Health Organisation international non-proprietary name
- trioxysalen
- defined daily dose
- 10
- subject has role
- photosensitizer
- found in taxon
- Apium graveolens
Sources (3)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Trioxsalen (trimethylpsoralen (TMP), trioxysalen (INN) 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 and hand eczema. 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. 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.
Trioxsalen (abbreviated as TMP) activated by UV-A exposure is commonly used in genetics research as an experimental mutagen. UV/TMP generates small deletions (~1-3 Kbp), but all base transitions and transversions can also be obtained.
Excerpted from Wikipedia’s “trioxsalen” article, available under the CC BY-SA 4.0 licence.