Drug/Small Molecule:
methoxsalen

2D structure

Overview

IUPAC Name: 9-methoxyfuro[3,2-g]chromen-7-one
Trade Names: Ammodin; Ammoidin; Meladinin; Meladinine; Meladoxen; Meloxine; Methoxa-Dome; Methoxalen; Methoxaten; New-Meladinin; Oxoralen; Oxsoralen; Oxsoralen Lotion; Oxsoralen-Ultra; Oxypsoralen; Proralone-Mop; Psoralen-Mop; Puvalen; Puvamet; Ultra Mop; Ultramop Lotion; Uvadex; Xanthotoxin; Xanthotoxine; Xanthoxin; Zanthotoxin
PharmGKB Accession Id: PA450433

Description

A naturally occurring furocoumarin compound found in several species of plants, including Psoralea corylifolia. It is a photoactive substance that forms DNA adducts in the presence of ultraviolet A irradiation. [PubChem]

Indication

For the treatment of psoriasis and vitiligo

ATC Therapeutic Categories

  • D05AD:Psoralens for topical use
  • D05BA:Psoralens for systemic use

Pharmacology and Interactions

Mechanism Of Action

After activation it binds preferentially to the guanine and cytosine moieties of DNA, leading to cross-linking of DNA, thus inhibiting DNA synthesis and function.

Pharmacology

Methoxsalen selectively inhibits the synthesis of deoxyribonucleic acid (DNA). The guanine and cytosine content correlates with the degree of Methoxsalen-induced cross-linking. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed.

Food Interactions

Take with food or milk, or in two divided doses 30 minutes apart to decrease nausea.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Half Life

Approximately 2 hours

Chemical Properties

Chemical Formula:

C12H8O4

SMILES Code:

COC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

216.1895 / 216.0423

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Metabolizing Enzymes

Drug Targets

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

ethotoin The hydantoin decreases the effect of psoralene
fosphenytoin The hydantoin decreases the effect of psoralene
mephenytoin The hydantoin decreases the effect of psoralene
phenytoin The hydantoin decreases the effect of psoralene

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

  1. The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease

LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00553
ChEBI ID:
18358
KEGG Compound ID:
C01864
KEGG Drug ID:
D00139
PubChem Compound ID:
4114
PubChem Substance ID:
152480

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
The PharmGKB is financially supported by the NIH/ NIGMS and is managed at Stanford University (U01GM61374).
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