TRIOXSALEN

US Previously Marketed

First approved in 1964

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 Search

SMILES

CC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O1

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
Sources: http://www.drugbank.ca/drugs/DB04571
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 282 Target ID: CHEMBL2311221 Sources: http://www.ncbi.nlm.nih.gov/pubmed/7499429	Crosslinking Agent 83

Conditions

Condition	Modality	Targets	Highest Phase	Product
Vitiligo 9 Sources: https://www.drugs.com/cons/trisoralen.html	Primary		Approved 8583	TRISORALEN Approved Use Trioxsalen Launch Date 1965

C_max

Value	Dose	Analyte	Population
12.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6177169/	0.6 mg/kg single, oral dose: 0.6 mg/kg route of administration: Oral experiment type: SINGLE co-administered:	TRIOXSALEN plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: FEMALE / MALE food status: UNKNOWN
31 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7236507/	400 mg 1 times / day unknown, oral dose: 400 mg route of administration: Oral experiment type: UNKNOWN co-administered:	TRIOXSALEN serum	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: FED
3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6155034/	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
2% REVIEW https://www.ncbi.nlm.nih.gov/pubmed/3512141	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:		TRIOXSALEN serum	Homo sapiens

Doses

Dose	Population	Adverse events
400 mg single, oral Highest studied dose Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7236507	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/7236507	Sources: https://pubmed.ncbi.nlm.nih.gov/7236507

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 2333	inhibitor 4027 Sources: https://link.springer.com/article/10.1007/s10930-011-9350-0	yes [Ki 0.1 uM]

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY552645	https://www.001chemical.com/chem/3902-71-4
3B Scientific (Wuhan) Corp	3B2-0791	http://www.3bsc.com/index/pro_info.php?id=20147
AA Blocks	AA003V2H	http://www.aablocks.com/goods/Goods/detail?id=AA003V2H
Aaron Chemicals	AR003VU9	http://www.aaronchem.com/3902-71-4
abcr GmbH	AB353283	http://www.abcr.com/shop/en/AB353283
abcr GmbH	AB541961	http://www.abcr.com/shop/en/AB541961
AbMole Bioscience	M6039	http://www.abmole.com/products/trioxsalen.html
Acadechem	ACDS-031978	http://www.acadechemical.com/product/106677
Achemo Scientific Limited	AC-13396	http://www.achemo.com/product_view.asp?ID=3286
Acros Organics	AC229880010	https://www.fishersci.com/shop/products/4-5-8-trimethylpsoralen-97-5-acros-organics/AC229880010
Acros Organics	AC229881000	https://www.fishersci.com/shop/products/4-5-8-trimethylpsoralen-97-5-acros-organics-1/AC229881000
AHH Chemical co.,ltd	API-1764	http://www.ahhchemical.com/product/API-1764.html
AK Scientific, Inc. (AKSCI)	J10195	http://www.aksci.com/item_detail.php?cat=J10195
AK Scientific, Inc. (AKSCI)	W0082	http://www.aksci.com/item_detail.php?cat=W0082
Alfa Chemistry	AP3902714-A	https://reagents.alfa-chemistry.com/product/trioxsalen-cas-3902-71-4-10986.html
Alfa Chemistry	AP3902714-B	https://reagents.alfa-chemistry.com/product/trioxsalen-cas-3902-71-4-10987.html
Ambinter	Amb20243178	http://www.ambinter.com/reference/20243178
Anward	ANW-41902	http://www.anward.com/pro_result/30156
Aurora Fine Chemicals LLC	A13.142.939	http://online.aurorafinechemicals.com/info?ID=A13.142.939
Aurum Pharmatech LLC	A-8462	http://www.Aurumpharmatech.com/Product/ProductDetails/A_8462
Avantor Inc	200002-802	https://us.vwr.com/store/product/18600871/trioxsalen-97-5
Chem Scene	CS-4760	http://www.chemscene.com/3902-71-4.html
Chemenu	CM110593	http://www.chemenu.com/products/CM110593
Chemspace	CSSB00000695135	https://chem-space.com/CSSB00000695135
Clearsynth	CS-O-02466	https://www.clearsynth.com/en/CSO02466.html
DC Chemicals	DC31903	http://www.dcchemicals.com//product_show-NSC71047.html
Debye Scientific	DB-049366	http://www.debyesci.com/cas_3902-71-4.html
Enamine	Z1551429738	https://www.enaminestore.com/catalog/Z1551429738
eNovation Chemicals	D673687	https://www.enovationchem.com/ProductDetails.asp?ProductID=D673687
Finetech	FT-0603651	http://www.finetechnology-ind.com/prod/detail/pub/3902-71-4.html
Glentham Life Sciences	GL4271	http://www.glentham.com/products/product/GL4271/
Lab Network	LN00196286	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00196286
LGC Standards	DRE-C17892400	https://www.lgcstandards.com/US/en/p/DRE-C17892400
mcule	MCULE-5301264270	https://mcule.com/MCULE-5301264270/
MedChem Express	HY-B1157	https://www.medchemexpress.com/Trioxsalen.html
Molcore	MC552645	https://www.molcore.com/product/3902-71-4
MuseChem	I003433	https://www.musechem.com/product/I003433.html
OChem	14218	http://www.ocheminc.com/index.php?act=psearch&pid=902T714
Sigma-Aldrich	1693009_USP	https://www.sigmaaldrich.com/catalog/product/usp/1693009?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	T6137_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/t6137?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S016321	http://www.sinfoobiotech.com/product/1019719
Smolecule	S005906	http://www.smolecule.com/products/s005906
Smolecule	S545922	http://www.smolecule.com/products/s545922
TCI (Tokyo Chemical Industry)	T2267	http://www.tcichemicals.com/eshop/en/us/commodity/T2267/index.html
THE BioTek	bt-255016	https://www.thebiotek.com/product/inhibitors/bt-255016
THE BioTek	bt-287039	https://www.thebiotek.com/product/inhibitors/bt-287039

PubMed

Title	Date	PubMed
RACK-1 acts with Rac GTPase signaling and UNC-115/abLIM in Caenorhabditis elegans axon pathfinding and cell migration.	2010-11-18	21124943
Analysis of active and inactive X chromosome architecture reveals the independent organization of 30 nm and large-scale chromatin structures.	2010-11-12	21070966
Conserved genes act as modifiers of invertebrate SMN loss of function defects.	2010-10-28	21124729
A developmental timing switch promotes axon outgrowth independent of known guidance receptors.	2010-08-05	20700435
Multivesicular body formation requires OSBP-related proteins and cholesterol.	2010-08-05	20700434
Structural determinants of photoreactivity of triplex forming oligonucleotides conjugated to psoralens.	2010-07-25	20725628
Rapid sampling of molecules via skin for diagnostic and forensic applications.	2010-07	20238151
Photoallergic contact dermatitis to 8-methoxypsoralen in Ficus carica.	2010-06	20557340
Whole-genome profiling of mutagenesis in Caenorhabditis elegans.	2010-06	20439774
Topical treatment in vitiligo and the potential uses of new drug delivery systems.	2010-05-07	20445292
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.	2010-01-25	20111596
Trioxsalen derivatives with lipoxygenase inhibitory activity.	2009-12	19912068
The germinal center kinase GCK-1 is a negative regulator of MAP kinase activation and apoptosis in the C. elegans germline.	2009-10-14	19826475
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.	2009-10	19192018
Cancer risk in hospitalised psoriasis patients: a follow-up study in Sweden.	2009-05-05	19352386
Electron microscopy methods for studying in vivo DNA replication intermediates.	2009	19563131
Nematode homologue of PQBP1, a mental retardation causative gene, is involved in lipid metabolism.	2009	19119319
An unexpectedly high degree of specialization and a widespread involvement in sterol metabolism among the C. elegans putative aminophospholipid translocases.	2008-10-02	18831765
The HLH-6 transcription factor regulates C. elegans pharyngeal gland development and function.	2008-10	18927627
3-Methyladenine DNA glycosylase is important for cellular resistance to psoralen interstrand cross-links.	2008-08-02	18571479
DNA interstrand crosslinks repair in mammalian cells.	2008-06-07	18533476
Application of TILLING and EcoTILLING as Reverse Genetic Approaches to Elucidate the Function of Genes in Plants and Animals.	2008-06	19452039
BINOL-amino acid conjugates as triggerable carriers of DNA-targeted potent photocytotoxic agents.	2007-12-27	18047263
Counting mutagenized genomes and optimizing genetic screens in Caenorhabditis elegans.	2007-11-07	17989770
In vivo footprint of a picornavirus internal ribosome entry site reveals differences in accessibility to specific RNA structural elements.	2007-11	17947530
Food deprivation attenuates seizures through CaMKII and EAG K+ channels.	2007-09	17941711
German evidence-based guidelines for the treatment of Psoriasis vulgaris (short version).	2007-06	17497162
Psoralen conjugates for visualization of genomic interstrand cross-links localized by laser photoactivation.	2007-03-22	17373769
Regulation of Caenorhabditis elegans body size and male tail development by the novel gene lon-8.	2007-03-20	17374156
Specific apoptosis induction in human papillomavirus-positive cervical carcinoma cells by photodynamic antisense regulation.	2007	17461764
Synthesis and biological in vitro evaluation of novel PEG-psoralen conjugates.	2006-12	17154485
TILLING is an effective reverse genetics technique for Caenorhabditis elegans.	2006-10-18	17049087
Permeability of psoralen derivatives in lipid membranes.	2006-10-01	16844741
Enhanced repair of DNA interstrand crosslinks in S phase.	2006-03-06	16494874
Properties of novel antisense oligonucleotides containing 2'-O-modified adenosine with a photo-reactive group.	2006	17150937
Occupational allergic contact dermatitis disseminated from multifunctional acrylates in ultraviolet-cured lacquers.	2006	16881602
Inhibition of interferon-gamma signaling by a mercurio-substituted dihydropsoralen in murine keratinocytes.	2005-12-05	16259964
Psoralen and coumarin photochemistry in HSA complexes and DMPC vesicles.	2005-09-10	16149848
Repair of DNA interstrand crosslinks may take place at the nuclear matrix.	2005-09-01	16052506
Psoralen photocrosslinking, a tool to study the chromatin structure of RNA polymerase I--transcribed ribosomal genes.	2005-08	16094448
Spectral study of interactions of 4,8,4'-trimethylpsoralen and 4,4'-dimethylangelicin dyes with DNA.	2005-07	16097948
Photoreaction of skin-sensitizing trimethyl psoralen with lipid membrane models.	2005-05-11	15882092
Disappearance of nucleosome positioning in mitotic chromatin in vivo.	2005-04-15	15705567
Interplay between human high mobility group protein 1 and replication protein A on psoralen-cross-linked DNA.	2005-03-22	15766246
5-(3-Phenylpropoxy)psoralen and 5-(4-phenylbutoxy)psoralen: mechanistic studies on phototoxicity.	2005-03	15801679
Synthesis and properties of photo-reactive antisense oligonucleotides containing 2'-O-psoralen-conjugated adenosine.	2005	17150768
Identification of ciliated sensory neuron-expressed genes in Caenorhabditis elegans using targeted pull-down of poly(A) tails.	2005	15693946
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.	2004-12	15611423
Tandem mass spectrometry for the determination of the sites of DNA interstrand cross-link.	2004-11	15519223
Psoralen derivatives and longwave ultraviolet irradiation are active in vitro against human melanoma cell line.	2004-10-25	15488715

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 `Mon Mar 31 18:31:05 GMT 2025` Edited by `admin` on `Mon Mar 31 18:31:05 GMT 2025`
Record UNII	Y6UY8OV51T
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TRIOXYSALEN

Preferred Name

English

TRIOXSALEN

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

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