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
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
DescriptionSources: http://www.drugbank.ca/drugs/DB04571Curator's Comment: description was created based on several sources, including: http://www.drugs.com/cons/trioxsalen.html
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2311221 Sources: http://www.ncbi.nlm.nih.gov/pubmed/7499429 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Sources: https://www.drugs.com/cons/trisoralen.html |
Primary | TRISORALEN Approved UseTrioxsalen Launch Date1965 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
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2% |
TRIOXSALEN serum | Homo sapiens |
PubMed
Title | Date | PubMed |
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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 |
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Tandem mass spectrometry for the determination of the sites of DNA interstrand cross-link. | 2004 Nov |
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Psoralen derivatives and longwave ultraviolet irradiation are active in vitro against human melanoma cell line. | 2004 Oct 25 |
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Synthesis and properties of photo-reactive antisense oligonucleotides containing 2'-O-psoralen-conjugated adenosine. | 2005 |
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Identification of ciliated sensory neuron-expressed genes in Caenorhabditis elegans using targeted pull-down of poly(A) tails. | 2005 |
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Disappearance of nucleosome positioning in mitotic chromatin in vivo. | 2005 Apr 15 |
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Psoralen photocrosslinking, a tool to study the chromatin structure of RNA polymerase I--transcribed ribosomal genes. | 2005 Aug |
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Inhibition of interferon-gamma signaling by a mercurio-substituted dihydropsoralen in murine keratinocytes. | 2005 Dec 5 |
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Spectral study of interactions of 4,8,4'-trimethylpsoralen and 4,4'-dimethylangelicin dyes with DNA. | 2005 Jul |
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5-(3-Phenylpropoxy)psoralen and 5-(4-phenylbutoxy)psoralen: mechanistic studies on phototoxicity. | 2005 Mar |
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Interplay between human high mobility group protein 1 and replication protein A on psoralen-cross-linked DNA. | 2005 Mar 22 |
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Repair of DNA interstrand crosslinks may take place at the nuclear matrix. | 2005 Sep 1 |
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Photoreaction of skin-sensitizing trimethyl psoralen with lipid membrane models. | 2005 Sep-Oct |
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Properties of novel antisense oligonucleotides containing 2'-O-modified adenosine with a photo-reactive group. | 2006 |
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Occupational allergic contact dermatitis disseminated from multifunctional acrylates in ultraviolet-cured lacquers. | 2006 |
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Synthesis and biological in vitro evaluation of novel PEG-psoralen conjugates. | 2006 Dec |
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Psoralen and coumarin photochemistry in HSA complexes and DMPC vesicles. | 2006 Jan-Feb |
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Enhanced repair of DNA interstrand crosslinks in S phase. | 2006 Mar 6 |
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Permeability of psoralen derivatives in lipid membranes. | 2006 Oct 1 |
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TILLING is an effective reverse genetics technique for Caenorhabditis elegans. | 2006 Oct 18 |
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BINOL-amino acid conjugates as triggerable carriers of DNA-targeted potent photocytotoxic agents. | 2007 Dec 27 |
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German evidence-based guidelines for the treatment of Psoriasis vulgaris (short version). | 2007 Jun |
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Regulation of Caenorhabditis elegans body size and male tail development by the novel gene lon-8. | 2007 Mar 20 |
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Psoralen conjugates for visualization of genomic interstrand cross-links localized by laser photoactivation. | 2007 Mar-Apr |
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In vivo footprint of a picornavirus internal ribosome entry site reveals differences in accessibility to specific RNA structural elements. | 2007 Nov |
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Counting mutagenized genomes and optimizing genetic screens in Caenorhabditis elegans. | 2007 Nov 7 |
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Food deprivation attenuates seizures through CaMKII and EAG K+ channels. | 2007 Sep |
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Specific apoptosis induction in human papillomavirus-positive cervical carcinoma cells by photodynamic antisense regulation. | 2007 Spring |
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3-Methyladenine DNA glycosylase is important for cellular resistance to psoralen interstrand cross-links. | 2008 Aug 2 |
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Application of TILLING and EcoTILLING as Reverse Genetic Approaches to Elucidate the Function of Genes in Plants and Animals. | 2008 Jun |
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DNA interstrand crosslinks repair in mammalian cells. | 2008 Mar-Apr |
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The HLH-6 transcription factor regulates C. elegans pharyngeal gland development and function. | 2008 Oct |
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An unexpectedly high degree of specialization and a widespread involvement in sterol metabolism among the C. elegans putative aminophospholipid translocases. | 2008 Oct 2 |
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Electron microscopy methods for studying in vivo DNA replication intermediates. | 2009 |
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Nematode homologue of PQBP1, a mental retardation causative gene, is involved in lipid metabolism. | 2009 |
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Trioxsalen derivatives with lipoxygenase inhibitory activity. | 2009 Dec |
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Cancer risk in hospitalised psoriasis patients: a follow-up study in Sweden. | 2009 May 5 |
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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 |
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The germinal center kinase GCK-1 is a negative regulator of MAP kinase activation and apoptosis in the C. elegans germline. | 2009 Oct 14 |
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A developmental timing switch promotes axon outgrowth independent of known guidance receptors. | 2010 Aug 5 |
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Multivesicular body formation requires OSBP-related proteins and cholesterol. | 2010 Aug 5 |
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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 |
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Rapid sampling of molecules via skin for diagnostic and forensic applications. | 2010 Jul |
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Structural determinants of photoreactivity of triplex forming oligonucleotides conjugated to psoralens. | 2010 Jul 25 |
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Photoallergic contact dermatitis to 8-methoxypsoralen in Ficus carica. | 2010 Jun |
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Whole-genome profiling of mutagenesis in Caenorhabditis elegans. | 2010 Jun |
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Topical treatment in vitiligo and the potential uses of new drug delivery systems. | 2010 May-Jun |
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Analysis of active and inactive X chromosome architecture reveals the independent organization of 30 nm and large-scale chromatin structures. | 2010 Nov 12 |
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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
Sources: http://www.drugs.com/cons/trioxsalen.html
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
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ACTIVE MOIETY