2-Desoxy-2-(((methylnitrosoamino)-carbonyl)amino)-D-glucopyranose
STZ · STREPTOZOCIN · STR · ZANOSAR · Streptozotocin (STZ) · Streptozotocin (U-9889) · beta-dimethylacrylshikonin · strz
Identifikatoren & physikalische Daten
| CAS No. | 18883-66-4 |
|---|---|
| Summenformel | C8H15N3O7 |
| Durchschnittliche Molmasse | 265,22 g/mol |
| Monoisotopische Masse | 265,09099983 g/mol |
| SMILES | CN(N=O)C(=O)NC(C=O)C(O)C(O)C(O)CO |
| InChIKey | AGRCPNMCOXLKFO-UHFFFAOYSA-N |
| PubChem CID | 5299 |
| Lokaler Name | 2-Desoxy-2-(((methylnitrosoamino)-carbonyl)amino)-D-glucopyranose |
Chemische & physikalische Eigenschaften
| XLogP | -3,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 160 |
| H-Brücken-Donoren | 5 |
| H-Brücken-Akzeptoren | 8 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 18 |
| Formalladung | 0 |
| Komplexität | 300 |
| Schmelzpunkt | 121 °C (dec.) (lit.) |
| Siedepunkt | 408.44°C (rough estimate) |
| Dichte | 1.4410 (rough estimate) |
| Brechungsindex | 1.6500 (estimate) |
| Lagerbedingungen | -20°C |
| Löslichkeit | Soluble in DMSO (up to 25 mg/ml) or in Water (up to 25 mg/ml) |
| Aggregatzustand | powder |
| pKa (Säurekonstante) | pKa 1.3 (Uncertain) |
| Farbe | white to light yellow |
| Merck | 13,8912 |
| BRN | 2060675 |
| Stabilität | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 1 month. |
| InChI | 1S/C8H15N3O7/c1-11(10-17)8(16)9-4-6(14)5(13)3(2-12)18-7(4)15/h3-7,12-15H,2H2,1H3,(H,9,16)/t3-,4-,5-,6-,7+/m1/s1 |
| InChIKey | ZSJLQEPLLKMAKR-FEQHFJGESA-N |
| SMILES | CN(N=O)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O |
| CAS Datenbank | 18883-66-4 |
| EPA chemische Informationen | Streptozotocin (18883-66-4) |
Sicherheit & Vorschriften
| F | 3-10-21 |
|---|---|
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | 3249 |
| Zollcode | 29419090 |
| RTECS-Nr. | LZ5775000 |
| R-Sätze (R) | 40-61-46-45-22-20/21/22 |
| Toxizität | LD50 in female mice (mg/kg): 360 i.p.275 i.v.in male dogs (mg/kg): 50 i.v. (Iwasaki) |
| Gefahrensymbole | Xn,T |
| Sicherheitshinweise (S) | 36/37-53-45-36-22 |
| Gefahrenklasse | 6.1(b)Carc. 2Flam. Sol. 1Muta. 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 4.1B - Flammable solid hazardous materials |
| Gefahrstoffdaten | 18883-66-4(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Streptozotocin (STZ) was originally identified in the late 1950s as an antibiotic and was discovered in a strain of the soil microbe Streptomyces achromogenes. In the mid-1960s, STZ was found to be selectively toxic to the beta cells of the pancreatic islets and thus it is used in animal model of diabetes and as a medical treatment for cancers of the beta cells. STZ’s use in cancer chemotherapy received Food and Drug Administration approval in July 1982 and the drug was subsequently marketed as Zanosar.
Verwenden
Streptozotocin is used in the treatment metastatic cancer of the pancreatic islet cells. Streptozotocin has a highlrisk of toxicity and is generally limited to cancers that are inoperable.