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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
Structure of METHOXSALEN

SMILES

COC1=C2OC(=O)C=CC2=CC3=C1OC=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

HIDE SMILES / InChI

Description
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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
8-MOP

Approved Use

when 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

1954
Primary
8-MOP

Approved Use

Photochemotherapy (methoxsalen with long wave ultraviolet radiation) is indicated for the repigmentation of idiopathic vitiligo

Launch Date

1954
Palliative
8-MOP

Approved Use

in 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

1954
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
127.63 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXSALEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
125.16 ng/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXSALEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
155 ng/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXSALEN serum
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: FASTED
129 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
335.48 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXSALEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
321.25 ng × h/mL
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXSALEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
420 ng × h/mL
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXSALEN serum
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: FASTED
521 ng × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
61 min
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHOXSALEN serum
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: FASTED
2.38 h
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

Doses

DosePopulationAdverse 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:
unhealthy, 49.7
Health Status: unhealthy
Age Group: 49.7
Sex: M+F
Sources:
70 mg 4 times / week multiple, oral
Recommended
Dose: 70 mg, 4 times / week
Route: oral
Route: multiple
Dose: 70 mg, 4 times / week
Sources:
unhealthy
Disc. AE: Cataract...
AEs leading to
discontinuation/dose reduction:
Cataract
Sources:
AEs

AEs

AESignificanceDosePopulation
Cataract Disc. AE
70 mg 4 times / week multiple, oral
Recommended
Dose: 70 mg, 4 times / week
Route: oral
Route: multiple
Dose: 70 mg, 4 times / week
Sources:
unhealthy
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical 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

Drug as victim

Tox targets
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Characterization of the mutational specificity of DNA cross-linking mutagens by the Lac+ reversion assay with Escherichia coli.
2001
Immunomodulating effects of extracorporeal photochemotherapy in rat experimental allergic encephalomyelitis.
2001
Phototherapy of psoriasis: comparative experience of different phototherapeutic approaches.
2001
Expression of CYP6B1 and CYP6B3 cytochrome P450 monooxygenases and furanocoumarin metabolism in different tissues of Papilio polyxenes (Lepidoptera: Papilionidae).
2001 Apr 27
A comparison of the effect of narrow-band ultraviolet B in the treatment of psoriasis after salt-water baths and after 8-methoxypsoralen baths.
2001 Aug
Plasma and skin concentration of 5-methoxypsoralen in psoriatic patients after oral administration.
2001 Aug
Assessment of the phototoxic potential of compounds and finished topical products using a human reconstructed epidermis.
2001 Fall
Livedoid vasculitis responding to PUVA therapy.
2001 Feb
Treatment of stage II cutaneous T-cell lymphoma with interferon alfa-2a and extracorporeal photochemotherapy: a prospective controlled trial.
2001 Feb
The PUVA-turban as a new option of applying a dilute psoralen solution selectively to the scalp of patients with alopecia areata.
2001 Feb
Pharmacokinetic behaviour of sublingually administered 8-methoxypsoralen for PUVA therapy.
2001 Feb
Aquagenic pruritus responding to intermittent photochemotherapy.
2001 Jan
Seville orange juice-felodipine interaction: comparison with dilute grapefruit juice and involvement of furocoumarins.
2001 Jan
[Heracl'eum mantegazzi'anum: photosensitization].
2001 Jan 18
Furanochromone radical cations: generation, characterization and interaction with DNA.
2001 Jul 2
Induction of apoptosis, depletion of glutathione, and DNA damage by extracorporeal photochemotherapy and psoralen with exposure to UV light in vitro.
2001 Jul-Aug
Extracorporeal photopheresis: a review.
2001 Jun
Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro.
2001 Jun
In vitro inhibition of cytochrome P450 enzymes in human liver microsomes by a potent CYP2A6 inhibitor, trans-2-phenylcyclopropylamine (tranylcypromine), and its nonamine analog, cyclopropylbenzene.
2001 Mar
Synthesis and properties of peptide nucleic acids containing a psoralen unit.
2001 Mar 22
The psoralens adversely affect reproductive function in male wistar rats.
2001 Mar-Apr
Evaluation of the immunomodulatory mechanisms of photochemotherapy in transplantation.
2001 May
The effect of methoxsalen dose on ultraviolet-A-induced erythema.
2001 May
A bioassay using the human hepatoblastoma cell line HepG2 for detecting phototoxicity of furocoumarins.
2001 Oct
Formation of 6-formyl-7-hydroxy-8-methoxycoumarin and 5,8-dioxopsoralen by reaction of 8-methoxypsoralen with H2O2 and potassium superoxide (KO2) catalyzed by halogenated or perhalogenated 5,10,15,20-tetraarylporphyrinatoiron(III) chlorides.
2001 Sep
Inhibition of itch-scratch response by fruits of Cnidium monnieri in mice.
2001 Sep
Is the efficacy of psoralen plus ultraviolet A therapy for vitiligo enhanced by concurrent topical calcipotriol? A placebo-controlled double-blind study.
2001 Sep
A study of the expression of the xenobiotic-metabolising cytochrome P450 proteins and of testosterone metabolism in bovine liver.
2001 Sep 1
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
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
Epoxidation of some natural furocoumarins and furochromones using gamma-ray.
2002 May-Jun
In vivo effect of 5- and 8-methoxypsoralens and cimetidine on R,S-warfarin metabolism in rat.
2002 Sep-Oct
Patents

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
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.
Name Type Language
METHOXSALEN
HSDB   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
8-MOP
Preferred Name English
VITPSO
Common Name English
METHOXSALEN [HSDB]
Common Name English
NSC-45923
Code English
XANTHOTOXIN
Common Name English
METHOXSALEN [USP MONOGRAPH]
Common Name English
SM-88 COMPONENT METHOXSALEN
Code English
8-METHOXYPSORALEN
Common Name English
OXYPSORALEN
Common Name English
METHOXSALEN [USP-RS]
Common Name English
METHOXSALEN [ORANGE BOOK]
Common Name English
METHOXSALEN [JAN]
Common Name English
Methoxsalen [WHO-DD]
Common Name English
9-Methoxy-7H-furo[3,2-g][1]benzopyran-7-one
Systematic Name English
METHOXSALEN [MART.]
Common Name English
UVADEX
Brand Name English
7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE, 9-METHOXY-
Systematic Name English
OXSORALEN
Brand Name English
METHOXSALEN [VANDF]
Common Name English
PUVALEN
Common Name English
METHOXSALEN [IARC]
Common Name English
8-METHOXSALEN
Common Name English
METHOXSALEN [MI]
Common Name English
METOXALEN
Common Name English
Classification Tree Code System Code
NDF-RT N0000010217
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
WHO-ATC D05AD02
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
WHO-ATC D05BA02
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
NDF-RT N0000007909
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
EU-Orphan Drug EU/3/06/374
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
WHO-VATC QD05AD02
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
FDA ORPHAN DRUG 80594
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
NCI_THESAURUS C1420
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
NDF-RT N0000007909
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
FDA ORPHAN DRUG 117298
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
NDF-RT N0000009801
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
NCI_THESAURUS C25760
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
WHO-VATC QD05BA02
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
NDF-RT N0000175879
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
NDF-RT N0000007909
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
FDA ORPHAN DRUG 74293
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
LIVERTOX 620
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NDF-RT N0000175984
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
Code System Code Type Description
DRUG CENTRAL
30
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
MERCK INDEX
m7329
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PRIMARY Merck Index
CAS
298-81-7
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PRIMARY
HSDB
2505
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PRIMARY
MESH
D008730
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PRIMARY
RS_ITEM_NUM
1417001
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PRIMARY
SMS_ID
100000092592
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PRIMARY
RXCUI
6854
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY RxNorm
WIKIPEDIA
METHOXSALEN
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
FDA UNII
U4VJ29L7BQ
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
DRUG BANK
DB00553
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
PUBCHEM
4114
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
CHEBI
18358
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
ECHA (EC/EINECS)
206-066-9
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
NSC
45923
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PRIMARY
NCI_THESAURUS
C643
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
DAILYMED
U4VJ29L7BQ
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
ChEMBL
CHEMBL416
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
EPA CompTox
DTXSID8020830
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
LACTMED
Methoxsalen
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY
EVMPD
SUB14541MIG
Created by admin on Mon Mar 31 17:45:47 GMT 2025 , Edited by admin on Mon Mar 31 17:45:47 GMT 2025
PRIMARY