Trioxsalen

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Trioxsalen

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Catalog Number	PR3902714
CAS	3902-71-4
Structure
Description	Trioxsalen is 7H-Furo[3,2-g]chromen-7-one in which positions 2, 5, and 9 are substituted by methyl groups. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered orally in conjunction with UV-A for phototherapy treatment of vitiligo. After photoactivation it creates interstrand cross-links in DNA, inhibiting DNA synthesis and cell division, and can lead to cell injury; recovery from the cell injury may be followed by increased melanisation of the epidermis. It has a role as a photosensitizing agent and a dermatologic drug.
Synonyms	Trisoralen
IUPAC Name	2,5,9-trimethylfuro[3,2-g]chromen-7-one
Molecular Weight	228.24
Molecular Formula	C14H12O3
InChI	FMHHVULEAZTJMA-UHFFFAOYSA-N
InChI Key	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
Drug Categories	Antipsoriatics; Antipsoriatics for Systemic Use; Antipsoriatics for Topical Use; Benzopyrans; Coumarins; Dermatologicals; Furocoumarins; Heterocyclic Compounds, Fused-Ring; Photosensitizing Agents; Photosensitizing Agents for Phototherapy; Psoralens for Systemic Use; Psoralens for Topical Use; Pyrans; Radiation-Sensitizing Agents
Drug Interactions	Acetohexamide-The therapeutic efficacy of Acetohexamide can be increased when used in combination with Trioxsalen. Chlorpropamide-The therapeutic efficacy of Chlorpropamide can be increased when used in combination with Trioxsalen. Dexmethylphenidate-The serum concentration of the active metabolites of Trioxsalen can be increased when Trioxsalen is used in combination with Dexmethylphenidate. Diazoxide-The serum concentration of Trioxsalen can be increased when it is combined with Diazoxide. Doxycycline-The therapeutic efficacy of Trioxsalen can be increased when used in combination with Doxycycline.
Isomeric SMILES	CC1=CC(=O)OC2=C1C=C3C=C(OC3=C2C)C
Type	Small Molecule

Pharmacology

Indications

Trioxsalen is a pigmenting photosensitizing agent specifically indicated for the treatment of vitiligo. It is utilized in conjunction with ultraviolet light to achieve optimal therapeutic outcomes, facilitating the repigmentation of affected skin areas.

Pharmacodynamics

While pharmacologically inactive on its own, trioxsalen undergoes activation through exposure to ultraviolet radiation or sunlight. This conversion to its active metabolite initiates a beneficial reaction in the skin, targeting and impacting the diseased tissues characteristic of vitiligo.

Mechanism of Action

Trioxsalen, upon undergoing photoactivation, facilitates the formation of interstrand cross-links within DNA. This process effectively interferes with cellular DNA replication and transcription, ultimately triggering the mechanism of programmed cell death. Such targeted action highlights Trioxsalen's potential in therapeutic applications where modulation of cellular proliferation is desired.

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