Methoxsalen

Synonyms :
6-Hydroxy-7-methoxy-5-benzofuranacrylic acid delta-lactone, 8-Methoxy-[furano-3′.2′:6.7-coumarin], 8-Methoxy-2′,3′,6,7-furocoumarin, 8-Methoxy-4′,5′:6,7-furocoumarin, 8-Methoxyfuranocoumarin, 8-Methoxypsoralen, 8-MOP, 8-MP, 9-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one, Ammoidin, Meladinine, Meloxine, Methoxalen, Methoxsalen, Méthoxsalène, O-Methylxanthotoxol, Oxsoralen, Ultra mop, Uvadex, Xanthotoxin, Xanthotoxine, Xanthoxin, Zanthotoxin

Status : approved

Category

Photosensitizing Agents

Therapeutic Classification

ANTIPSORIATICS FOR TOPICAL USE

DERMATOLOGICALS
ANTIPSORIATICS
ANTIPSORIATICS FOR TOPICAL USE
Cross-Linking Reagents

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]

Used

For the treatment of psoriasis and vitiligo

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.

Dosage

Form Route Strength
Capsule, gelatin coated oral 10 mg
Lotion topical 10 mg/mL
Lotion topical 10 mg
Capsule, liquid filled oral 10 mg
Capsule oral 10 mg
Liquid topical 1 %
Injection, solution extracorporeal 20 ug/mL
Solution extracorporeal 20 mcg

Pharmacodynamics

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.

Half Life

Approximately 2 hours

Elimination Route

In both mice and man, methoxsalen is rapidly metabolized. Approximately 95% of the drug is excreted as a series of metabolites in the urine within 24 hours (Pathak et al. 1977).

Chemical Classification

This compound belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group.

8-methoxypsoralens

Organic compounds

Phenylpropanoids and polyketides

Coumarins and derivatives

Furanocoumarins

Chemical Name

6-Hydroxy-7-methoxy-5-benzofuranacrylic acid delta-lactone

Brands

name Dosage form Country
8-mop capsule, gelatin coated US
Methoxsalen capsule, liquid filled US
Methoxsalen capsule, liquid filled US
Methoxsalen capsule, liquid filled US
Oxsoralen lotion US
Oxsoralen Cap 10mg capsule Canada
Oxsoralen Lot 10mg/ml lotion Canada
Oxsoralen-ultra capsule, liquid filled US
Oxsoralen-ultra Cap 10mg capsule Canada
Ultra Mop Lotion 1% liquid Canada
Ultramop Cap 10mg capsule Canada
Uvadex solution Canada
Uvadex injection, solution US

Drug Drug Interactions

  •  Agomelatine  : CYP1A2 Inhibitors (Strong) may increase the serum concentration of Agomelatine.
  •  Aripiprazole  : CYP2D6 Inhibitors (Weak) may increase the serum concentration of Aripiprazole.
  •  Bendamustine  : CYP1A2 Inhibitors (Strong) may increase the serum concentration of Bendamustine. Concentrations of the active metabolites of bendamustine may be decreased.
  •  Clozapine  : CYP1A2 Inhibitors (Strong) may increase the serum concentration of Clozapine.
  •  Duloxetine  : CYP1A2 Inhibitors (Strong) may increase the serum concentration of Duloxetine.
  •  Pentoxifylline  : CYP1A2 Inhibitors (Strong) may increase the serum concentration of Pentoxifylline.
  •  Pirfenidone  : CYP1A2 Inhibitors (Strong) may increase the serum concentration of Pirfenidone.
  •  Pomalidomide  : CYP1A2 Inhibitors (Strong) may increase the serum concentration of Pomalidomide.
  •  Porfimer  : May enhance the photosensitizing effect of Porfimer.
  •  Rasagiline  : CYP1A2 Inhibitors (Strong) may increase the serum concentration of Rasagiline.
  •  Tasimelteon  : CYP1A2 Inhibitors (Strong) may increase the serum concentration of Tasimelteon.
  •  Tizanidine  : CYP1A2 Inhibitors (Strong) may increase the serum concentration of Tizanidine.
  •  Verteporfin  : May enhance the photosensitizing effect of Verteporfin.

Food Interactions

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

Calculated Property

kind Value Source
logP 2.1 ALOGPS
logS -3.1 ALOGPS
Water Solubility 1.64e-01 g/l ALOGPS
logP 1.78 ChemAxon
IUPAC Name 9-methoxy-7H-furo[3,2-g]chromen-7-one ChemAxon
Traditional IUPAC Name methoxsalen ChemAxon
Molecular Weight 216.1895 ChemAxon
Monoisotopic Weight 216.042258744 ChemAxon
SMILES COC1=C2OC(=O)C=CC2=CC2=C1OC=C2 ChemAxon
Molecular Formula C12H8O4 ChemAxon
InChI InChI=1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3 ChemAxon
InChIKey InChIKey=QXKHYNVANLEOEG-UHFFFAOYSA-N ChemAxon
Polar Surface Area (PSA) 48.67 ChemAxon
Refractivity 56.85 ChemAxon
Polarizability 20.98 ChemAxon
Rotatable Bond Count 1 ChemAxon
H Bond Acceptor Count 2 ChemAxon
H Bond Donor Count 0 ChemAxon
pKa (strongest basic) -3.5 ChemAxon
Physiological Charge 0 ChemAxon
Number of Rings 3 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 0 ChemAxon

Affected organism

Humans and other mammals

Target within organism

  • DNA : in Human