CAS 3902-71-4|trioxsalen|2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one|trioxysalen|trisoralen|Trioxsalen|trimethylpsoralen|Trioxsalen|2,5,9-三甲基呋[3,2-g]苯并吡喃-7-酮|三甲沙林|三甲补骨脂内酯|4,5′,8-...

General Information

Structure

Molecular Formula

C₁₄H₁₂O₃

Molecular Mass

228.24328

Exact Mass

228.07864424

Charge

InChI

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

InChIKey

FMHHVULEAZTJMA-UHFFFAOYSA-N

Canonic Smiles

Cc1cc2c(o1)c(C)c1c(c2)c(C)cc(=O)o1

Isomeric Smiles

Cc1cc(=O)oc2c1cc1cc(oc1c2C)C

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

2.9548604

LogD (pH = 7.4)

2.9548604

Log P

2.9548604

Molar Refractivity

64.8626

Polarizability

25.444344

Polar Surface Area

39.44

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.26

LOG S

-3.56

Solubility (Water)

6.27e-02 g/l

Data Source

Commercial Catalog

Academic Data

Data Source

Names and Identifiers

Synonyms

trimethylpsoralentrisoralenTrioxsalentrioxysalenTrioxsalen三甲沙林2,5,9-三甲基呋[3,2-g]苯并吡喃-7-酮4,5′,8-三甲基补骨脂素TMP三甲补骨脂内酯Trioxsalen2,5,9-Trimethylfuro[3,2-g]benzopyran-7-one4,5',8-TRIMETHYLPSORALEN4,5′,8-Trimethylpsoralen2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-oneTripsosTrioxysalenDermetrixLevrison4,5',8-Trimethylpsoralen

IUPAC Traditional name

trioxsalen 2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one

IUPAC name

2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one

Names and Identifiers

Registration numbers

EC Number

MDL Number

CAS Number

Beilstein Number

PubChem SID

2488964424900351160967571

PubChem CID

DrugBank ID

ATC CODE

CHEBI ID

Chemspider ID

CHEMBL

Unique Ingredient Identifier

Y6UY8OV51T

KEGG ID

D01034

Wikipedia Title

Trioxsalen

Registration numbers

Properties

Safety Information

-20°C

Room Temperature (15-30°C), Protect from light

R:34

34-40

LV1576000

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Selleck Chemicals

S2022

Research Area: Immunology
Biological Activity:
Trioxsalen(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 vitiligo and hand eczema. 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. 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. [1]

MP Biomedicals

02154157

Potent photosensitizing agent; rapid and sensitive assay for interstrand DNA cross links: Biochemistry, 20: 143, (1981).

DrugBank

DB04571

Drug Groups

approved

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 ultraviolet 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 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.

Indication

Trioxsalen is a pigmenting photosensitizing agent used in conjunction with ultraviolet light in the treatment of vitiligo.

Pharmacology

Trioxsalen ispharmacologically inactive but when exposed to ultraviolet radiation or sunlight it is converted to its active metabolite to produce a beneficial reaction affecting the diseased tissue.

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]

• 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]

• 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]

External Links

• [Wikipedia]

• [Drugs.com]

Wikipedia

Trioxsalen

Sigma Aldrich

T6137

包装
1 g in glass bottle
100, 500 mg in glass bottle
Biochem/physiol Actions
DNA 的光化学交联剂，可作为探针用于核酸结构和功能研究。三甲沙林也用于使 DNA 在云母表面交联。

861391

Biochem/physiol Actions
Photochemical crosslinker of DNA that has been used as a probe for nucleic acid structure and function. Trioxsalen has also been used to crosslink DNA onto mica surfaces.

92895

Biochem/physiol Actions
Photochemical crosslinker of DNA that has been used as a probe for nucleic acid structure and function. Trioxsalen has also been used to crosslink DNA onto mica surfaces.

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Trioxsalen

• Thompson, H.J. et al., J. Chromatogr., 1984, 314, 323, (hplc)

• Hassan, M.A., Anal. Profiles Drug Subst., 1981, 10, 705, (rev)

• Elgamal, M.H.A. et al., Phytochemistry, 1979, 18, 139, (cmr)

• Gencheva, M. et al., J. Biol. Chem., 1996, 271, 2608, (pharmacol)

• Caporale, G. et al., Experientia, 1967, 23, 985, (pharmacol)

• Bender, D.R. et al., J.O.C., 1979, 44, 2176, (synth)

• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1098

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 684C, (ir)

• Dimitrova, D. et al., Nucleic Acids Res., 1993, 21, 5554, (pharmacol)

• Scheel, L.D. et al., Biochemistry, 1963, 2, 1127, (isol)

• Taskineu, J. et al., Biomed. Mass Spectrom., 1980, 7, 556, (ms)

• Russev, G. et al., J. Mol. Biol., 1982, 161, 77, (pharmacol)

• Nivsarkar, M. et al., Biochem. Mol. Biol. Int., 1996, 38, 625, (pharmacol)

• Kaufman, K.D., J.O.C., 1961, 26, 117; 1980, 45, 738, (synth, uv)

• IARC Monog., 1986, 40, 357; Suppl. 7, 366; Suppl. 6, 541, (rev, tox)

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Commercial Catalog

• Academic Data

Names and Identifiers

• Synonyms

• IUPAC Traditional name

• IUPAC name

Registration numbers

• EC Number

• MDL Number

• CAS Number

• Beilstein Number

• PubChem SID

• PubChem CID

• DrugBank ID

• ATC CODE

• CHEBI ID

• Chemspider ID

• CHEMBL

• Unique Ingredient Identifier

• KEGG ID

• Wikipedia Title

Registration numbers

Properties

• Safety Information

• Product Information

• Physical Property

• Pharmacology Properties

Related Proteins

Molecular Spectra

Molecule Details

• Selleck Chemicals

• MP Biomedicals

• DrugBank

• Wikipedia

• Sigma Aldrich

Molecule Details

References

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

Synonyms

IUPAC Traditional name

trioxsalen 2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one

IUPAC name

2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one

MDL Number

MFCD00005010

CAS Number

3902-71-4

Beilstein Number

221723

Unique Ingredient Identifier

Wikipedia Title

S2022

Potent photosensitizing agent; rapid and sensitive assay for interstrand DNA cross links: Biochemistry, 20: 143, (1981).

DrugBank

DB04571

Drug Groups

approved

Description

Indication

Trioxsalen is a pigmenting photosensitizing agent used in conjunction with ultraviolet light in the treatment of vitiligo.

Pharmacology

Trioxsalen ispharmacologically inactive but when exposed to ultraviolet radiation or sunlight it is converted to its active metabolite to produce a beneficial reaction affecting the diseased tissue.

References

External Links

• [Wikipedia]

• [Drugs.com]

Sigma Aldrich

T6137

861391

Biochem/physiol Actions
Photochemical crosslinker of DNA that has been used as a probe for nucleic acid structure and function. Trioxsalen has also been used to crosslink DNA onto mica surfaces.

92895

Biochem/physiol Actions
Photochemical crosslinker of DNA that has been used as a probe for nucleic acid structure and function. Trioxsalen has also been used to crosslink DNA onto mica surfaces.

From Data Sources

• http://en.wikipedia.org/wiki/Trioxsalen

• Thompson, H.J. et al., J. Chromatogr., 1984, 314, 323, (hplc)

• Hassan, M.A., Anal. Profiles Drug Subst., 1981, 10, 705, (rev)

• Elgamal, M.H.A. et al., Phytochemistry, 1979, 18, 139, (cmr)

• Gencheva, M. et al., J. Biol. Chem., 1996, 271, 2608, (pharmacol)

• Caporale, G. et al., Experientia, 1967, 23, 985, (pharmacol)

• Bender, D.R. et al., J.O.C., 1979, 44, 2176, (synth)

• Martindale, The Extra Pharmacopoeia, 31st edn., Pharmaceutical Press, 1996, 1098

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 684C, (ir)

• Dimitrova, D. et al., Nucleic Acids Res., 1993, 21, 5554, (pharmacol)

• Scheel, L.D. et al., Biochemistry, 1963, 2, 1127, (isol)

• Taskineu, J. et al., Biomed. Mass Spectrom., 1980, 7, 556, (ms)

• Russev, G. et al., J. Mol. Biol., 1982, 161, 77, (pharmacol)

• Nivsarkar, M. et al., Biochem. Mol. Biol. Int., 1996, 38, 625, (pharmacol)

• Kaufman, K.D., J.O.C., 1961, 26, 117; 1980, 45, 738, (synth, uv)

• IARC Monog., 1986, 40, 357; Suppl. 7, 366; Suppl. 6, 541, (rev, tox)

Safety Information

-20°C

Room Temperature (15-30°C), Protect from light

R:34

34-40

LV1576000

Safety Statements

S:26-27/28-36/37/39-46-64

26-36/37/39-45

European Hazard Symbols

Corrosive (C)

MSDS Link

Download link

German water hazard class

Personal Protective Equipment

Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

GHS Precautionary statements

P280-P305+P351+P338-P310

GHS Hazard statements

H314-H351

Packing Group

GHS Pictograms

Corrosive to metals, category 1

Skin corrosion, categories 1A,1B,1C

Serious eye damage, category 1

Respiratory sensitization, category 1

Germ cell mutagenicity, categories 1A,1B,2

Carcinogenicity, categories 1A,1B,2

Reproductive toxicity, categories 1A,1B,2

Specific Target Organ Toxicity – Single exposure, categories 1,2

Specific Target Organ Toxicity – Repeated exposure, categories 1,2

Aspiration Hazard, category 1

GHS Signal Word

Danger

Hazard Class

RID/ADR

UN 1759 8/PG 1

UN Number

1759

Storage Temperature

-20°C

2-8°C

Product Information

Physical Property

Pharmacology Properties

Mechanism of Action

Action depends on the presence of functional melanocytes and their proliferation by photoactivated drug

Conjugates and forms covalent-bonds with DNA which leads to the formation of both monofunctional and bifunctional adducts upon photoactivation

Exact mechanism with epidermal melanocytes and keratinocytes unknown.

Molecule

ID:4139