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Details

Stereochemistry ACHIRAL
Molecular Formula C14H12O3
Molecular Weight 228.2433
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIOXSALEN

SMILES

CC1=CC2=C(O1)C(C)=C3OC(=O)C=C(C)C3=C2

InChI

InChIKey=FMHHVULEAZTJMA-UHFFFAOYSA-N
InChI=1S/C14H12O3/c1-7-4-12(15)17-14-9(3)13-10(6-11(7)14)5-8(2)16-13/h4-6H,1-3H3

HIDE SMILES / InChI

Molecular Formula C14H12O3
Molecular Weight 228.2433
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: http://www.drugs.com/cons/trioxsalen.html

Trioxsalen (trimethylpsoralen, trioxysalen or trisoralen) is a furanocoumarin and a psoralen derivative. It is obtained from several plants, mainly Psoralea corylifolia. Like other psoralens it causes photosensitization of the skin. It is administered either topically or orally in conjunction with UV-A (the least damaging form of ultraviolet light) for phototherapy treatment of vitiligo1 and hand eczema.2 After photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death unless repaired by cellular mechanisms. In research it can be conjugated to dyes for confocal microscopy and used to visualize sites of DNA damage.3 The compound is also being explored for development of antisense oligonucleotides that can be cross-linked specifically to a mutant mRNA sequence without affecting normal transcripts differing at even a single base pair.Trioxsalen was discontinued by the manufacturer in December 2002.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2311221
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TRISORALEN

Approved Use

Trioxsalen

Launch Date

1965
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3 ng/mL
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TRIOXSALEN plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
TRIOXSALEN serum
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
400 mg single, oral
Highest studied dose
Dose: 400 mg
Route: oral
Route: single
Dose: 400 mg
Sources:
unhealthy, adult
n = 1
Health Status: unhealthy
Age Group: adult
Population Size: 1
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [Ki 0.1 uM]
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Photodynamic antisense regulation of human cervical carcinoma cell growth using psoralen-conjugated oligo(nucleoside phosphorothioate).
2001 Apr
Zygotic expression of the caudal homolog pal-1 is required for posterior patterning in Caenorhabditis elegans embryogenesis.
2001 Jan 1
[Application of gauze with metallic inclusions for the treatment of purulent wounds].
2002 Nov-Dec
An intraindividual comparative study of psoralen-UVA erythema induced by bath 8-methoxypsoralen and 4, 5', 8-trimethylpsoralen.
2003 Jul
Photoreaction of skin-sensitizing trimethyl psoralen with lipid membrane models.
2005 Sep-Oct
Counting mutagenized genomes and optimizing genetic screens in Caenorhabditis elegans.
2007 Nov 7
Food deprivation attenuates seizures through CaMKII and EAG K+ channels.
2007 Sep
Specific apoptosis induction in human papillomavirus-positive cervical carcinoma cells by photodynamic antisense regulation.
2007 Spring
Electron microscopy methods for studying in vivo DNA replication intermediates.
2009
Trioxsalen derivatives with lipoxygenase inhibitory activity.
2009 Dec
Role of tacrolimus (FK506) 0.1% ointment WW in vitiligo in children and imperatives of combine therapy with Trioxsalen and Silymarin suspension in progressive vitiligo.
2009 Oct
The germinal center kinase GCK-1 is a negative regulator of MAP kinase activation and apoptosis in the C. elegans germline.
2009 Oct 14
A developmental timing switch promotes axon outgrowth independent of known guidance receptors.
2010 Aug 5
Multivesicular body formation requires OSBP-related proteins and cholesterol.
2010 Aug 5
Structural determinants of photoreactivity of triplex forming oligonucleotides conjugated to psoralens.
2010 Jul 25
Photoallergic contact dermatitis to 8-methoxypsoralen in Ficus carica.
2010 Jun
Topical treatment in vitiligo and the potential uses of new drug delivery systems.
2010 May-Jun
Analysis of active and inactive X chromosome architecture reveals the independent organization of 30 nm and large-scale chromatin structures.
2010 Nov 12
Patents

Sample Use Guides

In Vivo Use Guide
for vitiligo: Adults and children 12 years of age and over—20 to 40 milligrams (mg) taken two to four hours before ultraviolet light A (UVA) exposure. This treatment (trioxsalen and UVA) is given two or three times a week with the treatments spaced at least forty-eight hours apart.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:33:02 GMT 2023
Edited
by admin
on Fri Dec 15 16:33:02 GMT 2023
Record UNII
Y6UY8OV51T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRIOXSALEN
MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
TMP (PSORALEN)
Common Name English
Trioxysalen [WHO-DD]
Common Name English
4,5',8-TRIMETHYLPSORALEN
Common Name English
trioxysalen [INN]
Common Name English
TRIOXSALEN [USP IMPURITY]
Common Name English
TRIOXSALEN [USAN]
Common Name English
7H-FURO(3,2-G)(1)BENZOPYRAN-7-ONE, 2,5,9-TRIMETHYL-
Systematic Name English
TRIOXSALEN [MI]
Common Name English
2,5,9-Trimethyl-7H-furo[3,2-g][1]benzopyran-7-one
Systematic Name English
TRIOXYSALEN [MART.]
Common Name English
NSC-71047
Code English
TRISORALEN
Brand Name English
TRIOXYSALEN
INN   JAN   MART.   WHO-DD  
INN  
Official Name English
4,5',8-TRIMETHYLPSORALEN [IARC]
Common Name English
TRIOXSALEN [VANDF]
Common Name English
TRIOXSALEN [ORANGE BOOK]
Common Name English
TRIOXYSALEN [JAN]
Common Name English
TRIOXSALEN [USP-RS]
Common Name English
Classification Tree Code System Code
NDF-RT N0000007909
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
NDF-RT N0000175879
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
WHO-VATC QD05AD01
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
WHO-ATC D05AD01
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
WHO-ATC D05BA01
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
NDF-RT N0000007909
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
NCI_THESAURUS C29708
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
WHO-VATC QD05BA01
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
NDF-RT N0000007909
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID3023716
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY
EVMPD
SUB11318MIG
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY
SMS_ID
100000076929
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY
DRUG CENTRAL
2759
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY
RS_ITEM_NUM
1693009
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY
MERCK INDEX
m11177
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY Merck Index
CAS
3902-71-4
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY
ChEMBL
CHEMBL1475
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY
ECHA (EC/EINECS)
223-459-0
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY
RXCUI
10844
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C66640
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY
NSC
71047
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY
PUBCHEM
5585
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY
INN
2064
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY
DRUG BANK
DB04571
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY
MESH
D014307
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY
CHEBI
28329
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY
WIKIPEDIA
TRIOXSALEN
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY
FDA UNII
Y6UY8OV51T
Created by admin on Fri Dec 15 16:33:02 GMT 2023 , Edited by admin on Fri Dec 15 16:33:02 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY