| Common Name |
Trioxsalen
| Description |
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 litraviolet light) for phototherapy treatment of vitiligo[1] and hand eczema.[2] After photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death unless repaired by cellliar 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.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
2',4,8-TrimethylpsoralenChEBI
4,5',8-TrimethylpsoralenChEBI
4,8,5'-TrimethylpsoralenChEBI
6-Hydroxy-beta,2,7-trimethyl-5-benzofuranacrylic acid, delta-lactoneChEBI
TrimethylpsoralenChEBI
TrioxisalenoChEBI
TrioxysalenChEBI
TrioxysaleneChEBI
TrioxysalenumChEBI
6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylate, delta-lactoneGenerator
6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylic acid, delta-lactoneGenerator
6-Hydroxy-beta,2,7-trimethyl-5-benzofuranacrylate, delta-lactoneGenerator
6-Hydroxy-β,2,7-trimethyl-5-benzofuranacrylate, δ-lactoneGenerator
6-Hydroxy-β,2,7-trimethyl-5-benzofuranacrylic acid, δ-lactoneGenerator
6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylate, δ-lactoneGenerator
6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylic acid, δ-lactoneGenerator
TrisoralenHMDB
TrioxisalenumMeSH
2,5,9-Trimethyl-7H-furo(3,2-g)benzopyran-7-oneMeSH
ICN brand OF trioxsalenMeSH
| Chemical Formlia |
C14H12O3
| Average Molecliar Weight |
228.2433
| Monoisotopic Molecliar Weight |
228.07864425
| IUPAC Name |
2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one
| Traditional Name |
trioxsalen
| CAS Registry Number |
3902-71-4
| SMILES |
CC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O1
| InChI Identifier |
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
| InChI Key |
FMHHVULEAZTJMA-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Phenylpropanoids and polyketides
| Sub Class |
Coumarins and derivatives
| Direct Parent |
Psoralens
| Alternative Parents |
1-benzopyrans
Benzofurans
Pyranones and derivatives
Benzenoids
Heteroaromatic compounds
Furans
Lactones
Oxacyclic compounds
Organooxygen compounds
Organic oxides
Hydrocarbon derivatives
| Substituents |
Psoralen
Benzopyran
1-benzopyran
Benzofuran
Pyranone
Benzenoid
Pyran
Furan
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
psoralens (CHEBI:28329 )
Furanocoumarins (C09314 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Drug
| Biofunction |
Photosensitizing Agents
| Application |
Pharmaceutical
| Cellliar locations |
Cytoplasm
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.063 mg/mLALOGPS
logP3.26ALOGPS
logP2.95ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.44 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity64.86 m3·mol-1ChemAxon
Polarizability24.77 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
| Biofluid Locations |
Blood
Urine
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Biofluid |
Status |
Age |
Condition |
Reference |
Details |
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04571
21059682
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04571
21059682
details
|
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
DB04571
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
Not Available
| KNApSAcK ID |
Not Available
| Chemspider ID |
5383
| KEGG Compound ID |
C09314
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Trioxsalen
| NuGOwiki Link |
HMDB15575
| Metagene Link |
HMDB15575
| METLIN ID |
Not Available
| PubChem Compound |
5585
| PDB ID |
Not Available
| ChEBI ID |
28329
Product: Carbenicillin
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- van Coevorden AM, Kamphof WG, van Sonderen E, Bruynzeel DP, Coenraads PJ: 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. Arch Dermatol. 2004 Dec;140(12):1463-6. [PubMed:15611423 ]
- Higuchi M, Yamayoshi A, Kobori A, Yamaoka T, Murakami A: Synthesis and properties of photo-reactive antisense oligonucleotides containing 2-O-psoralen-conjugated adenosine. Nucleic Acids Symp Ser (Oxf). 2005;(49):331-2. [PubMed:17150768 ]
- Thazhathveetil AK, Liu ST, Indig FE, Seidman MM: Psoralen conjugates for visualization of genomic interstrand cross-links localized by laser photoactivation. Bioconjug Chem. 2007 Mar-Apr;18(2):431-7. [PubMed:17373769 ]
|
PMID: 22363498
