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Details

Stereochemistry ACHIRAL
Molecular Formula C14H12O3
Molecular Weight 228.2433
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIOXSALEN

SMILES

CC1=CC2=C(O1)C(C)=C3OC(=O)C=C(C)C3=C2

InChI

InChIKey=FMHHVULEAZTJMA-UHFFFAOYSA-N
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

HIDE SMILES / InChI

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.Trioxsalen was discontinued by the manufacturer in December 2002.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TRISORALEN

Cmax

ValueDoseCo-administeredAnalytePopulation
3 ng/mL
40 mg single, oral
TRIOXSALEN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
TRIOXSALEN serum
Homo sapiens

Doses

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

PubMed

Sample Use Guides

In Vivo Use Guide
for vitiligo: Adults and children 12 years of age and over—20 to 40 milligrams (mg) taken two to four hours before ultraviolet light A (UVA) exposure. This treatment (trioxsalen and UVA) is given two or three times a week with the treatments spaced at least forty-eight hours apart.
Route of Administration: Oral
In Vitro Use Guide
Unknown