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
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 |
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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Photodynamic antisense regulation of human cervical carcinoma cell growth using psoralen-conjugated oligo(nucleoside phosphorothioate). | 2001 Apr |
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Zygotic expression of the caudal homolog pal-1 is required for posterior patterning in Caenorhabditis elegans embryogenesis. | 2001 Jan 1 |
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[Application of gauze with metallic inclusions for the treatment of purulent wounds]. | 2002 Nov-Dec |
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An intraindividual comparative study of psoralen-UVA erythema induced by bath 8-methoxypsoralen and 4, 5', 8-trimethylpsoralen. | 2003 Jul |
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Photoreaction of skin-sensitizing trimethyl psoralen with lipid membrane models. | 2005 Sep-Oct |
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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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Electron microscopy methods for studying in vivo DNA replication intermediates. | 2009 |
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Trioxsalen derivatives with lipoxygenase inhibitory activity. | 2009 Dec |
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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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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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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
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
Substance Class |
Chemical
Created
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Record UNII |
Y6UY8OV51T
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Validated (UNII)
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N0000007909
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N0000175879
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QD05AD01
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D05AD01
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D05BA01
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N0000007909
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C29708
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WHO-VATC |
QD05BA01
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NDF-RT |
N0000007909
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DB04571
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D014307
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TRIOXSALEN
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Y6UY8OV51T
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Related Record | Type | Details | ||
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