2-Desoxy-2-(((methylnitrosoamino)-carbonyl)amino)-D-glucopyranose Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R40:Verdacht auf krebserzeugende Wirkung.
R61:Kann das Kind im Mutterleib schädigen.
R46:Kann vererbbare Schäden verursachen.
R45:Kann Krebs erzeugen.
R22:Gesundheitsschädlich beim Verschlucken.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S22:Staub nicht einatmen.
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.
Chemische Eigenschaften
off-white to pale yellow crystalline powder
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.
Indications
Streptozocin (Zanosar), a water-soluble nitrosourea
produced by the fungus Streptomyces achromogenes,
acts through methylation of nucleic acids and proteins.
In addition, it produces rapid and severe depletion of
the pyridine nucleotides nicotinamide adenine dinucleotide
(NAD) and its reduced form (NADH) in liver
and pancreatic islets.
Streptozocin is not well absorbed from the gastrointestinal
tract and must be administered intravenously or
intraarterially. In preclinical studies, the plasma half-life
was 5 to 10 minutes.
Streptozocin produces remission in 50 to 60% of patients
with islet cell carcinomas of the pancreas. It is also
useful in malignant carcinoid tumors.
Almost all patients have nausea and vomiting. The
major toxicity is renal tubular damage, which may be severe
in 5 to 10% of patients taking streptozocin.
Treatment of metastatic insulinomas may result in the
release of insulin from the tumor and subsequent hypoglycemic
coma. Less severe toxicities include diarrhea,
anemia, and mild alterations in glucose tolerance or
liver function tests.
Definition
ChEBI: An antibiotic that is produced by Streptomyces achromogenes. It is used as an antineoplastic agent and to induce diabetes in experimental animals.
Allgemeine Beschreibung
Off-white powder. Melting point 115°C. Used as an anti-cancer drug. Carcinogenic.
Air & Water Reaktionen
Water soluble.
Reaktivität anzeigen
[D-GLUCOSE, 2-DEOXY-2-[[(METHYLNITROSOAMINO)-CARBONYL]AMINO] is weakly basic. Reacts exothermically with acids. Reacts with both strong oxidizing agents and strong reducing agents.
Biologische Aktivität
Antibiotic and antitumor agent. Alkylates DNA and induces diabetes mellitus via reduction of nicotinamide adenine dinucleotide in pancreatic β -cells in vivo .
Clinical Use
The glucopyranose moiety of streptozocin confers both islet cell specificity and high water solubility to this nitrosourea-based antineoplastic. As a result, it is used exclusively in metastatic islet cell carcinoma of the pancreas and is administered IV in D5W or normal saline.
Nebenwirkungen
Lacking the 2-chloroethyl substituent of carmustine and lomustine, it is much less reactive as a DNA alkylating agent, and myelotoxicity is relatively rare but not unknown. Cumulative, dose-related renal toxicity can be severe or fatal, however, and 67% of patients receiving this drug will exhibit some kidney-related pathology.
Sicherheitsprofil
Confirmed carcinogen with experimental carcinogenic, neoplas tigenic, tumorigenic, and teratogenic data. Experimental poison by intravenous, parenteral, subcutaneous, and intraperitoneal routes. Moderately toxic to humans by intravenous route. Human systemic effects: nausea or vomiting, impaired liver function, kidney changes. Human mutation data reported. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx. See also NITROSAMINES.
Carcinogenicity
Streptozotocin is reasonably anticipated to be a human carcinogenbased on sufficient evidence of carcinogenicity from studies in experimental animals.
Environmental Fate
STZ is an odorless ivory-colored crystalline powder or pale
yellow crystals. Having the solubility of 5070 mg l
-1 in water at
25 °C, STZ is soluble in alcohol and ketones and slightly
soluble in polar organic solvents and insoluble in nonpolar
organic solvents. STZ is produced by the soil microorganism
and therefore isolated from soil samples that assumed a source
of release to the environment. Vapor pressure and Henry’s law
constant of STZ are 1.74E-12 mm Hg and 1.08E-10 cm3 per
molecule-sec at 25 °C, respectively. No information is currently
available for partition behavior in water, sediment, and soil;
environmental persistency, long-range transport, or bioaccumulation/
biomagnification.
läuterung methode
Recrystallise streptozotocin from 95% EtOH. It is soluble in H2O, MeOH and Me2CO. It has UV max at 228nm ( 6360) in EtOH. The tetraacetate has m 111-114o(dec), and [] D 25 +41o (c 0.78, 95% EtOH) after recrystallisation from EtOAc. [Herr et al. J Am Chem Soc 89 4808 1967, NMR: Wiley et al. J Org Chem 44 9 1979.] It is a potent methylating agent for DNA [Bennett & Pegg Cancer Res 41 2786 1981].
2-Desoxy-2-(((methylnitrosoamino)-carbonyl)amino)-D-glucopyranose Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
