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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

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
Comparison of oral psoralen-UV-A with a portable tanning unit at home vs hospital-administered bath psoralen-UV-A in patients with chronic hand eczema: an open-label randomized controlled trial of efficacy.
2004 Dec
Tandem mass spectrometry for the determination of the sites of DNA interstrand cross-link.
2004 Nov
Psoralen derivatives and longwave ultraviolet irradiation are active in vitro against human melanoma cell line.
2004 Oct 25
Synthesis and properties of photo-reactive antisense oligonucleotides containing 2'-O-psoralen-conjugated adenosine.
2005
Identification of ciliated sensory neuron-expressed genes in Caenorhabditis elegans using targeted pull-down of poly(A) tails.
2005
Disappearance of nucleosome positioning in mitotic chromatin in vivo.
2005 Apr 15
Psoralen photocrosslinking, a tool to study the chromatin structure of RNA polymerase I--transcribed ribosomal genes.
2005 Aug
Inhibition of interferon-gamma signaling by a mercurio-substituted dihydropsoralen in murine keratinocytes.
2005 Dec 5
Spectral study of interactions of 4,8,4'-trimethylpsoralen and 4,4'-dimethylangelicin dyes with DNA.
2005 Jul
5-(3-Phenylpropoxy)psoralen and 5-(4-phenylbutoxy)psoralen: mechanistic studies on phototoxicity.
2005 Mar
Interplay between human high mobility group protein 1 and replication protein A on psoralen-cross-linked DNA.
2005 Mar 22
Repair of DNA interstrand crosslinks may take place at the nuclear matrix.
2005 Sep 1
Photoreaction of skin-sensitizing trimethyl psoralen with lipid membrane models.
2005 Sep-Oct
Properties of novel antisense oligonucleotides containing 2'-O-modified adenosine with a photo-reactive group.
2006
Occupational allergic contact dermatitis disseminated from multifunctional acrylates in ultraviolet-cured lacquers.
2006
Synthesis and biological in vitro evaluation of novel PEG-psoralen conjugates.
2006 Dec
Psoralen and coumarin photochemistry in HSA complexes and DMPC vesicles.
2006 Jan-Feb
Enhanced repair of DNA interstrand crosslinks in S phase.
2006 Mar 6
Permeability of psoralen derivatives in lipid membranes.
2006 Oct 1
TILLING is an effective reverse genetics technique for Caenorhabditis elegans.
2006 Oct 18
BINOL-amino acid conjugates as triggerable carriers of DNA-targeted potent photocytotoxic agents.
2007 Dec 27
German evidence-based guidelines for the treatment of Psoriasis vulgaris (short version).
2007 Jun
Regulation of Caenorhabditis elegans body size and male tail development by the novel gene lon-8.
2007 Mar 20
Psoralen conjugates for visualization of genomic interstrand cross-links localized by laser photoactivation.
2007 Mar-Apr
In vivo footprint of a picornavirus internal ribosome entry site reveals differences in accessibility to specific RNA structural elements.
2007 Nov
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
3-Methyladenine DNA glycosylase is important for cellular resistance to psoralen interstrand cross-links.
2008 Aug 2
Application of TILLING and EcoTILLING as Reverse Genetic Approaches to Elucidate the Function of Genes in Plants and Animals.
2008 Jun
DNA interstrand crosslinks repair in mammalian cells.
2008 Mar-Apr
The HLH-6 transcription factor regulates C. elegans pharyngeal gland development and function.
2008 Oct
An unexpectedly high degree of specialization and a widespread involvement in sterol metabolism among the C. elegans putative aminophospholipid translocases.
2008 Oct 2
Electron microscopy methods for studying in vivo DNA replication intermediates.
2009
Nematode homologue of PQBP1, a mental retardation causative gene, is involved in lipid metabolism.
2009
Trioxsalen derivatives with lipoxygenase inhibitory activity.
2009 Dec
Cancer risk in hospitalised psoriasis patients: a follow-up study in Sweden.
2009 May 5
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
Two very long chain fatty acid acyl-CoA synthetase genes, acs-20 and acs-22, have roles in the cuticle surface barrier in Caenorhabditis elegans.
2010 Jan 25
Rapid sampling of molecules via skin for diagnostic and forensic applications.
2010 Jul
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
Whole-genome profiling of mutagenesis in Caenorhabditis elegans.
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
RACK-1 acts with Rac GTPase signaling and UNC-115/abLIM in Caenorhabditis elegans axon pathfinding and cell migration.
2010 Nov 18
Conserved genes act as modifiers of invertebrate SMN loss of function defects.
2010 Oct 28
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
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
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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
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PRIMARY
EVMPD
SUB11318MIG
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PRIMARY
SMS_ID
100000076929
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PRIMARY
DRUG CENTRAL
2759
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PRIMARY
RS_ITEM_NUM
1693009
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PRIMARY
MERCK INDEX
m11177
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PRIMARY Merck Index
CAS
3902-71-4
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PRIMARY
ChEMBL
CHEMBL1475
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PRIMARY
ECHA (EC/EINECS)
223-459-0
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PRIMARY
RXCUI
10844
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PRIMARY RxNorm
NCI_THESAURUS
C66640
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PRIMARY
NSC
71047
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PRIMARY
PUBCHEM
5585
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PRIMARY
INN
2064
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PRIMARY
DRUG BANK
DB04571
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PRIMARY
MESH
D014307
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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