Structure via PubChem · Public domain (PubChem)
methoxsalen
Sign in to saveAlso known as Meladinine, 8-MOP, 8-Methoxy-2',3',6,7-furocoumarin, 9-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one, Meloxine, Ultra mop, Oxsoralen-Ultra, 6,7-furocoumarin
Methoxsalen (or Xanthotoxin, 8-methoxypsoralen) sold under the brand name Oxsoralen and Melanocyl among others, is a medication used to treat psoriasis, eczema, vitiligo, and some cutaneous lymphomas in conjunction with exposing the skin to ultraviolet (UVA) light from lamps or sunlight. Methoxsalen modifies the way skin cells receive the UVA radiation, allegedly clearing up the disease. Levels of individual patient PUVA exposure were originally determined using the Fitzpatrick scale. The scale was developed after patients demonstrated symptoms of phototoxicity after oral ingestion of methoxsa
Chemical data
- Formula
- C12H8O4
- Molecular weight
- 216.19 g/mol
- IUPAC name
- 9-methoxyfuro[3,2-g]chromen-7-one
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1954
- Admin. routes
- oral, parenteral, topical
- Indications
- lymphoma, mycosis fungoides, acute graft vs. host disease, Crohn's disease
via ChEMBL · EBI
Research
2,658 papers- Methoxsalen.IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans · 1980
- Methoxsalen-induced macular toxicity.Indian journal of ophthalmology · 2017
- Methoxsalen-induced advanced bull's eye maculopathy.European journal of ophthalmology · 2021
- Clinical pharmacokinetics of methoxsalen and other psoralens.Clinical pharmacokinetics · 1986
- Methoxsalen Inhibits the Acquisition of Nicotine Self-Administration: Attenuation by Cotinine Replacement in Male Rats.Nicotine & tobacco research : official journal of the Society for Research on Nicotine and Tobacco · 2024
via PubMed
Wikidata facts
- Subclass of
- furanocoumarin
- Mass
- 216.042
- Has use
- medication
Show 9 more facts
- chemical formula
- C₁₂H₈O₄
- medical condition treated
- graft-versus-host disease
- canonical SMILES
- COC1=C2C(=CC3=C1OC=C3)C=CC(=O)O2
- defined daily dose
- 10
- subject has role
- carcinogen
- melting point
- 148
- found in taxon
- Arabidopsis thaliana
- has characteristic
- bitterness
- legal status (medicine)
- boxed warning
via Wikidata · CC0
~4 min read
Encyclopedic overview
7 sectionsContents
- Natural sources
- Biosynthesis
- Synthesis of umbelliferone
- Synthesis of methoxsalen
- Risks and side effects
- Society and culture
- References
Methoxsalen (or Xanthotoxin, 8-methoxypsoralen) sold under the brand name Oxsoralen and Melanocyl among others, is a medication used to treat psoriasis, eczema, vitiligo, and some cutaneous lymphomas in conjunction with exposing the skin to ultraviolet (UVA) light from lamps or sunlight. Methoxsalen modifies the way skin cells receive the UVA radiation, allegedly clearing up the disease. Levels of individual patient PUVA exposure were originally determined using the Fitzpatrick scale. The scale was developed after patients demonstrated symptoms of phototoxicity after oral ingestion of methoxsalen followed by PUVA therapy. Chemically, methoxsalen is a derivative of psoralen and belongs to a class of organic natural molecules known as furanocoumarins. They consist of coumarin annulated with furan. It can also be injected and used topically.
== Natural sources == In 1947, methoxsalen was isolated (under the name "ammoidin") from the plant Ammi majus, bishop's weed.
Excerpted from Wikipedia’s “methoxsalen” article, available under the CC BY-SA 4.0 licence.
Gallery (5)
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via Wikidata sitelinks · CC0