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Teniposid
etp · vehem · vm-26 · Vumon · Eniposide · nsc122819 · Teniposid · Tenoposide
Identifikatoren & physikalische Daten
| CAS No. | 29767-20-2 |
|---|---|
| Summenformel | C32H32O13S |
| Durchschnittliche Molmasse | 656,7 g/mol |
| Monoisotopische Masse | 656,15636224 g/mol |
| SMILES | COc1cc([C@@H]2c3cc4c(cc3[C@@H](O[C@@H]3O[C@@H]5COC(c6cccs6)O[C@H]5[C@H](O)[C@H]3O)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1O |
| InChIKey | NRUKOCRGYNPUPR-PSZSYXFXSA-N |
| PubChem CID | 34698 |
| ChEBI | CHEBI:75988 |
| Lokaler Name | Teniposid |
Chemische & physikalische Eigenschaften
| XLogP | 1,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 189 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 14 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 46 |
| Formalladung | 0 |
| Komplexität | 1.090 |
| LogP (Verteilungskoeffizient) | 1.5 |
| Löslichkeit | 5.98e-02 g/LDMSO: soluble10mg/mL, clear |
| Physical Description | Solid |
| Schmelzpunkt | 244-247°C |
| Siedepunkt | 650.86°C (rough estimate) |
| Dichte | 1.2568 (rough estimate) |
| Brechungsindex | 1.5530 (estimate) |
| Lagerbedingungen | -20°C |
| pKa (Säurekonstante) | 10.13(at 25℃) |
| Aggregatzustand | powder |
| Farbe | white to beige |
| Merck | 14,9145 |
| Stabilität | Hygroscopic |
| InChIKey | NRUKOCRGYNPUPR-QBPJDGROSA-N |
| SMILES | [s]1c(ccc1)[C@H]2O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)O)O[C@H]4[C@@H]5[C@@H]([C@@H](c7c4cc8c(c7)OCO8)c6cc(c(c(c6)OC)O)OC)C(=O)OC5)CO2 |
| CAS Datenbank | 29767-20-2(CAS DataBase Reference) |
Sicherheit & Vorschriften
| Toxizitätsübersicht | The mechanism of action appears to be related to the inhibition of type II topoisomerase activity since teniposide does not intercalate into DNA or bind strongly to DNA. Teniposide binds to and inhibits DNA topoisomerase II. The cytotoxic effects of teniposide are related to the relative number of double-stranded DNA breaks produced in cells, which are a reflection of the stabilization of a topoisomerase II-DNA intermediate. |
|---|---|
| Carcinogen Classification | 2A, probably carcinogenic to humans. (L135) |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 2811 6.1 / PGIII |
| Zollcode | 29349990 |
| RTECS-Nr. | KC0180000 |
| R-Sätze (R) | 36/37/38-45 |
| Toxizität | LD50 intraperitoneal in mouse: 29570ug/kg |
| Gefahrensymbole | Xi,T |
| Sicherheitshinweise (S) | 26-36-45-53 |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 29767-20-2(Hazardous Substances Data) |
| Gefahrenklasse | Carc. 1B |
Anwendungen & Verwendung
Verwenden
Teniposide is a podophyllotoxin derivative that causes dose-dependent single- and double-stranded breaks in DNA by inhibiting topoisomerase II. Its cytostatic effects are related to its ability to stabilize the DNA-topoisomerase II complex during DNA replication, inducing DNA damage and cellular apoptosis. Teniposide has been widely used in the treatment of various cancers including, small cell lung cancer, malignant lymphoma, breast cancer, oral squamous cell carcinoma, and acute lymphoblastic leukemia.