Grundinformationen
- CAS
3902-71-4- Standard-SMILES
Cc1cc2cc3c(C)cc(=O)oc3c(C)c2o1- InChIKey
FMHHVULEAZTJMA-UHFFFAOYSA-N- Summenformel
- C14H12O3
- Durchschnittliche Molmasse
- 228,24 g/mol
- Monoisotopische Masse
- 228,07864424
Überblick
Trioxsalen is 7H-Furo[3,2-g]chromen-7-one in which positions 2, 5, and 9 are substituted by methyl groups. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered orally in conjunction with UV-A for phototherapy treatment of vitiligo. After photoactivation it creates interstrand cross-links in DNA, inhibiting DNA synthesis and cell division, and can lead to cell injury; recovery from the cell injury may be followed by increased melanisation of the epidermis. It has a role as a photosensitizing agent and a dermatologic drug.
Namen und Bezeichner
- Bevorzugter Name
- Trimethylpsoralen
- IUPAC
- 2,5,9-trimethylfuro[3,2-g]chromen-7-one
- Lokaler Name
- Trioxysalen
- Englischer Name
- TRIOXSALEN
- Summenformel
- C14H12O3
- Molmasse
- 228.24
Namen und Synonyme
trioxsalen3902-71-4TrioxysalenTrimethylpsoralen4,5',8-TrimethylpsoralenTrioxisalenoTrioxysalene2',4,8-TrimethylpsoralenTrioxysalenumNSC710472,5,9-trimethylfuro[3,2-g]chromen-7-oneTmp (psoralen)
Weitere Namen anzeigen
LACTONENSC-71047TrioxalenTrioxsaleTrixsalenrioxsalenTRISORALENElder 8011
DTXSID3023716NSC 710477H-Furo[3,2-g][1]benzopyran-7-one, 2,5,9-trimethyl-Y6UY8OV51T2,5,9-Trimethyl-7H-furo(3,2-g)(1)benzopyran-7-one7H-Furo(3,2-g)(1)benzopyran-7-one, 2,5,9-trimethyl-2,5,9-Trimethyl-7H-furo[3,2-g][1]benzopyran-7-oneDTXCID403716
Datenbank-Bezeichner
- CAS
3902-71-4- PubChem CID
- 5585
- DTXSID
DTXSID3023716- ChEMBL
CHEMBL1475- ChEBI
CHEBI:28329
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3
- Polarare Oberfläche (TPSA)
- 39,4 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 17
- Formalladung
- 0
- Komplexität
- 374
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesFusion temperature
LogP3.25
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physical DescriptionSolid
Collision Cross Section
147.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
146.69 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 229 · 229-231 °C(lit.)
- Siedepunkt
- 310.05 °C · 310.05°C (rough estimate)
- Dichte
- 1.2196 · 1.2196 (rough estimate)
- Brechungsindex
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P203, P260, P264, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P318, P321, P363, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Other Safety InformationIMAP assessments - 7H-Furo[3,2-g][1]benzopyran-7-one, 2,5,9-trimethyl-: Human health tier I assessment
Hazard Classes and CategoriesSkin Corr. 1B (100%)
Toxikologische Informationen
Carcinogen Classification
4,5',8-Trimethylpsoralen
Group 3: Not classifiable as to its carcinogenicity to humans
Volume 40: (1986) Some Naturally Occurring and Synthetic Food Components, Furocoumarins and Ultraviolet Radiation
1987
1987
Sicherheitsdaten
- F
- 8-10
- wgk
- 2
- tsca
- TSCA listed
- ridadr
- UN 1759 8/PG 1
- hs_code
- 29322985
- RTECS-Nr.
- LV1576000
- risk_code
Chemie und Industrie
Pharmakologische Informationen
ATC Code
D - Dermatologicals
D - Dermatologicals
QD - Dermatologicals
QD - Dermatologicals
PharmacodynamicsTrioxsalen 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.
Mechanism of ActionAfter photoactivation it creates interstrand cross-links in DNA, which can cause programmed cell death.
FDA Pharmacological Classification
Y6UY8OV51T
TRIOXSALEN
Established Pharmacologic Class [EPC] - Psoralen
Chemical Structure [CS] - Psoralens
Trioxsalen is a Psoralen.
MeSH Pharmacological Classification
Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or systemically and have been used therapeutically to treat psoriasis and various types of neoplasms.
Cellular LocationsCytoplasm
Verwendung und Herstellung
General Manufacturing Information7H-Furo[3,2-g][1]benzopyran-7-one, 2,5,9-trimethyl-: INACTIVE
Anwendungen
VerwendenTrioxsalen has been used: to induce small deletion mutations in worms in combination with ultraviolet A (UVA) to induce interstrand crosslinks (ICLs) in DNA for the preparation and photoactivation of trimethyl psoralen
Zugehörige Reaktionen
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