Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H8O4 |
Molecular Weight | 216.1895 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C2OC=CC2=CC3=C1OC(=O)C=C3
InChI
InChIKey=QXKHYNVANLEOEG-UHFFFAOYSA-N
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
Molecular Formula | C12H8O4 |
Molecular Weight | 216.1895 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/09048slr037_methoxsalen_lbl.pdfCurator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB00553
https://en.wikipedia.org/wiki/Methoxsalen
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2003/09048slr037_methoxsalen_lbl.pdf
Curator's Comment: description was created based on several sources, including:
http://www.drugbank.ca/drugs/DB00553
https://en.wikipedia.org/wiki/Methoxsalen
Methoxsalen — also called xanthotoxin, marketed under the trade names Oxsoralen, Deltasoralen, Meladinine — is a drug used to treat psoriasis, eczema, vitiligo, and some cutaneous lymphomas in conjunction with exposing the skin to UVA light from lamps or sunlight. Methoxsalen modifies the way skin cells receive the UVA radiation, allegedly clearing up the disease. The dosage comes in 10 mg tablets, which are taken in the amount of 30 mg 75 minutes before a PUVA (psoralen + UVA) light treatment. Chemically, methoxsalen 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. The exact mechanism of action of methoxsalen with the epidermal melanocytes and keratinocytes is not known. The best known biochemical reaction of methoxsalen is with DNA. Methoxsalen, upon photoactivation, conjugates and forms covalent bonds with DNA which leads to the formation of both monofunctional (addition to a single strand of DNA) and bifunctional adducts (crosslinking of psoralen to both strands of DNA) Reactions with proteins have also been described. Methoxsalen acts as a photosensitizer. Administration of the drug and subsequent exposure to UVA can lead to cell injury. Orally administered methoxsalen reaches the skin via the blood and UVA penetrates well into the skin. If sufficient cell injury occurs in the skin, an inflammatory reaction occurs. The most obvious manifestation of this reaction is delayed erythema, which may not begin for several hours and peaks at 48–72 hours. The inflammation is followed, over several days to weeks, by repair which is manifested by increased melanization of the epidermis and thickening of the stratum corneum. The mechanisms of therapy are not known. In the treatment of vitiligo, it has been suggested that melanocytes in the hair follicle are stimulated to move up the follicle and to repopulate the epidermis. In the treatment of psoriasis, the mechanism is most often assumed to be DNA photodamage and resulting decrease in cell proliferation but other vascular, leukocyte, or cell regulatory mechanisms may also be playing some role. Psoriasis is a hyperproliferative disorder and other agents known to be therapeutic for psoriasis are known to inhibit DNA synthesis. The most commonly reported side effect of methoxsalen alone is nausea, which occurs with approximately 10% of all patients. This effect may be minimized or avoided by instructing the patient to take methoxsalen with milk or food, or to divide the dose into two portions, taken approximately one-half hour apart. Other effects include nervousness, insomnia, and psychological depression.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2311221 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | 8-MOP Approved Usewhen the diagnosis has been supported by biopsy. Photochemotherapy is intended to be administered only in conjunction
with a schedule of controlled doses of long wave ultraviolet radiation. Launch Date-4.75804795E11 |
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Primary | 8-MOP Approved UsePhotochemotherapy (methoxsalen with long wave ultraviolet radiation) is indicated for the repigmentation
of idiopathic vitiligo Launch Date-4.75891204E11 |
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Palliative | 8-MOP Approved Usein the palliative treatment of the skin manifestations of cutaneous T-cell lymphoma (CTCL) in persons who have not been responsive to other forms of treatment. While this dosage form of methoxsalen has been approved for use in combination with photopheresis, Oxsoralen Ultra Capsules have not been approved for that use. Launch Date-4.75891204E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
129 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3729509 |
0.6 mg/kg single, oral dose: 0.6 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
METHOXSALEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
521 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3729509 |
0.6 mg/kg single, oral dose: 0.6 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
METHOXSALEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.38 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3729509 |
0.6 mg/kg single, oral dose: 0.6 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
METHOXSALEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
0.6 mg/kg 4 times / week multiple, oral Recommended Dose: 0.6 mg/kg, 4 times / week Route: oral Route: multiple Dose: 0.6 mg/kg, 4 times / week Sources: Page: p.103 |
unhealthy, 49.7 n = 14 Health Status: unhealthy Condition: Palmoplantar eczema Age Group: 49.7 Sex: M+F Population Size: 14 Sources: Page: p.103 |
|
70 mg 4 times / week multiple, oral (max) Recommended Dose: 70 mg, 4 times / week Route: oral Route: multiple Dose: 70 mg, 4 times / week Co-administed with:: UVA Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Psoriasis Sources: Page: p.5 |
Disc. AE: Cataract... AEs leading to discontinuation/dose reduction: Cataract Sources: Page: p.5 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Cataract | Disc. AE | 70 mg 4 times / week multiple, oral (max) Recommended Dose: 70 mg, 4 times / week Route: oral Route: multiple Dose: 70 mg, 4 times / week Co-administed with:: UVA Sources: Page: p.5 |
unhealthy Health Status: unhealthy Condition: Psoriasis Sources: Page: p.5 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
yes [IC50 2 uM] | ||||
yes [Ki 0.11 uM] | ||||
yes [Ki 0.2 uM] | ||||
yes [Ki 0.8 uM] | ||||
yes [Ki 20 uM] | ||||
yes [Ki 20 uM] | ||||
yes [Ki 25 uM] | ||||
yes [Ki 3 uM] | ||||
yes [Ki 35 uM] | ||||
yes [Ki 75 uM] | ||||
yes | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: (PMDA infomation form) 19 |
yes | |||
Page: (PMDA infomation form) 19 |
yes | |||
Page: (PMDA infomation form) 19 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Serum folate levels after UVA exposure: a two-group parallel randomised controlled trial. | 2001 |
|
Can a mixed damage interfere with DNA-protein cross-links repair? | 2001 Apr-Jun |
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Acitretin therapy for palmoplantar pustulosis combined with UVA and topical 8-MOP. | 2001 Aug |
|
Developmental variation in cytochrome P450 expression in Papilio polyxenes in response to xanthotoxin, a hostplant allelochemical. | 2001 Dec |
|
Photosensitization and mutation induced in Escherichia coli and Saccharomyces cerevisiae strains by dorstenin, a psoralen analog isolated from Dorstenia bahiensis. | 2001 Dec |
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Systemic allergic contact dermatitis to 8-methoxypsoralen (8-MOP). | 2001 Dec |
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S. cerevisiae has three pathways for DNA interstrand crosslink repair. | 2001 Dec 19 |
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Assessment of the phototoxic potential of compounds and finished topical products using a human reconstructed epidermis. | 2001 Fall |
|
Localized vitiligo successfully treated with cream-psoralen + ultraviolet A. | 2001 Jul |
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What's new in the treatment of vitiligo. | 2001 Jul |
|
Induction of apoptosis, depletion of glutathione, and DNA damage by extracorporeal photochemotherapy and psoralen with exposure to UV light in vitro. | 2001 Jul-Aug |
|
Anaphylaxis to 5-methoxypsoralen during photochemotherapy. | 2001 Nov |
|
PUVA downregulates whn expression in primary mouse keratinocytes. | 2001 Nov 1 |
|
Photoclastogenicity-an improved protocol, its validation, and investigation of the photogenotoxicity of DMBA. | 2002 |
|
Can the immersion time of PUVA bath therapy be shortened? | 2002 |
|
Characteristics of photopheresis treatments for the management of rejection in heart and lung transplant recipients. | 2002 |
|
Amino acids in SRS1 and SRS6 are critical for furanocoumarin metabolism by CYP6B1v1, a cytochrome P450 monooxygenase. | 2002 Apr |
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Chalcones and other constituents of Dorstenia prorepens and Dorstenia zenkeri. | 2002 Apr |
|
Effects of storage conditions on furocoumarin levels in intact, chopped, or homogenized parsnips. | 2002 Apr 24 |
|
Studies on mechanism of 8-methoxypsoralen-DNA interaction in the dark. | 2002 Apr 26 |
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[Acute generalized exanthematous pustulosis due to meladinine with positive patch tests]. | 2002 Feb |
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Mitochondrial alterations in fanconi anemia fibroblasts following ultraviolet A or psoralen photoactivation. | 2002 Feb |
|
Effects of the isoflavone 4',5,7-trihydroxyisoflavone (genistein) on psoralen plus ultraviolet A radiation (PUVA)-induced photodamage. | 2002 Feb |
|
Synthesis and biological evaluation of a new furo[2,3-h]quinolin-2(1H)-one. | 2002 Feb 28 |
|
Evaluation of synergism in the feeding deterrence of some furanocoumarins on Spodoptera littoralis. | 2002 Jan |
|
Extracorporeal photopheresis in cutaneous T-cell lymphoma and graft-versus-host disease induces both immediate and progressive apoptotic processes. | 2002 Jan |
|
Reliability of nested polymerase chain reaction in the diagnosis of bacterial endophthalmitis. | 2002 Jan |
|
Cell-impermeant pyridinium derivatives of psoralens as inhibitors of keratinocyte growth. | 2002 Jan 1 |
|
Changes in skin physiology during bath PUVA therapy. | 2002 Jul |
|
Extracorporeal photochemotherapy: a new therapeutic approach for allograft rejection. | 2002 Jun |
|
T cell clonality and the effect of photopheresis in systemic sclerosis and graft versus host disease. | 2002 Jun |
|
Transimmunization and the evolution of extracorporeal photochemotherapy. | 2002 Jun |
|
Severe influenzalike symptoms associated with methoxsalen photochemotherapy. | 2002 Jun |
|
A melanocyte-keratinocyte coculture model to assess regulators of pigmentation in vitro. | 2002 Jun 15 |
|
Time course of 8-methoxypsoralen concentrations in skin and plasma after topical (bath and cream) and oral administration of 8-methoxypsoralen. | 2002 Mar |
|
Decreased survival of UV-irradiated Staphylococcus aureus in the presence of 8-methoxypsoralen in the post-irradiation plating medium. | 2002 Mar |
|
Bullous phytophotodermatitis associated with high natural concentrations of furanocoumarins in limes. | 2002 Mar |
|
Novel angular furo and thieno-quinolinones: synthesis and preliminary photobiological studies. | 2002 Mar |
|
Simultaneous determination of furanocoumarins in infusions and decoctions from "Carapiá" (dorstenia species) by high-performance liquid chromatography. | 2002 Mar 13 |
|
3-Alkyl- and 3-aryl-7H-furo[3,2-g]-1-benzopyran-7-ones: synthesis, photoreactivity, and fluorescence properties. | 2002 May |
|
Differential effect of 8-methoxypsoralen, 4,6,4'-trimethylangelicin, and chlorpromazine on cell death and TNF-alpha production. | 2002 May |
|
Werner syndrome diploid fibroblasts are sensitive to 4-nitroquinoline-N-oxide and 8-methoxypsoralen: implications for the disease phenotype. | 2002 May |
|
p53 and Fas ligand are required for psoralen and UVA-induced apoptosis in mouse epidermal cells. | 2002 May |
|
Synthesis, photobiological activity and photoreactivity of methyl-thieno-8-azacoumarins, novel bioisosters of psoralen. | 2002 May 6 |
|
Epoxidation of some natural furocoumarins and furochromones using gamma-ray. | 2002 May-Jun |
|
Oral administration of 5-methoxypsoralen affects the distribution and metabolism of 2-aminofluorene in Sprague-Dawley rats. | 2002 May-Jun |
|
Phytochemical and pharmacological studies on Sideritis taurica Stephan ex Wild. | 2002 Oct |
|
DNA cross-link-dependent RAD50/MRE11/NBS1 subnuclear assembly requires the Fanconi anemia C protein. | 2002 Oct 1 |
|
Tea: not immoral, illegal, or fattening, but is it innocuous? | 2002 Sep 14 |
|
In vivo effect of 5- and 8-methoxypsoralens and cimetidine on R,S-warfarin metabolism in rat. | 2002 Sep-Oct |
Sample Use Guides
VITILIGO THERAPY : Two capsules (10 mg each) in one dose taken with milk or in food two to four hours before ultraviolet light exposure.
PSORIASIS THERAPY: The methoxsalen capsules should be taken 2 hours before UVA exposure with some food or milk
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3114156
Curator's Comment: 8-Methoxypsoralen was assessed for its effects on in vitro lymphocyte proliferation in the absence of ultraviolet radiation. 8-Methoxypsoralen inhibited both the phytohemagglutinin and concanavalin A-induced proliferation of normal human peripheral blood lymphocytes in a time and dose-dependent manner.
8-Methoxypsoralen inhibited both the phytohemagglutinin and concanavalin A-induced proliferation of normal human peripheral blood lymphocytes in a time and dose-dependent manner.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:04:59 UTC 2023
by
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on
Fri Dec 15 15:04:59 UTC 2023
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Record UNII |
U4VJ29L7BQ
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000010217
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WHO-ATC |
D05AD02
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WHO-ATC |
D05BA02
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NDF-RT |
N0000007909
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EU-Orphan Drug |
EU/3/06/374
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WHO-VATC |
QD05AD02
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FDA ORPHAN DRUG |
80594
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NCI_THESAURUS |
C1420
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NDF-RT |
N0000007909
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FDA ORPHAN DRUG |
117298
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NDF-RT |
N0000009801
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NCI_THESAURUS |
C25760
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WHO-VATC |
QD05BA02
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NDF-RT |
N0000175879
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NDF-RT |
N0000007909
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FDA ORPHAN DRUG |
74293
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LIVERTOX |
620
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NDF-RT |
N0000175984
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30
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m7329
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PRIMARY | Merck Index | ||
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298-81-7
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2505
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D008730
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1417001
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100000092592
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6854
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PRIMARY | RxNorm | ||
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METHOXSALEN
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U4VJ29L7BQ
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DB00553
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4114
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18358
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206-066-9
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45923
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C643
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U4VJ29L7BQ
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CHEMBL416
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DTXSID8020830
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Methoxsalen
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SUB14541MIG
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY |