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2-Desoxy-2-(((methylnitrosoamino)-carbonyl)amino)-D-glucopyranose Produkt Beschreibung

CAS-Nr.18883-66-4
Bezeichnung:2-Desoxy-2-(((methylnitrosoamino)-carbonyl)amino)-D-glucopyranose
Englisch Name:Streptozocin
Synonyma:
STR;STZ;strz;U-9889;ZANOSAR;nsc85998;nsc-85598;nsc-85998;nci-c03167;STREPTOZOCIN
CBNumber:CB1476758
Summenformel:C8H15N3O7
Molgewicht:265.22
MOL-Datei:18883-66-4.mol
2-Desoxy-2-(((methylnitrosoamino)-carbonyl)amino)-D-glucopyranose physikalisch-chemischer Eigenschaften
Schmelzpunkt:: 121 °C (dec.)(lit.)
alpha : D25 +39°
Siedepunkt:: 408.44°C (rough estimate)
Dichte: 1.4410 (rough estimate)
Brechungsindex: 1.6500 (estimate)
storage temp. : −20°C
pka: pKa 1.3 (Uncertain)
Aggregatzustand: powder
Farbe: white to light yellow
Wasserlöslichkeit: soluble
Sensitive : Hygroscopic
Merck : 13,8912
BRN : 2060675
InChIKey: ZSJLQEPLLKMAKR-FEQHFJGESA-N
CAS Datenbank: 18883-66-4
EPA chemische Informationen: D-Glucose, 2-deoxy-2-[[(methylnitrosoamino) carbonyl]amino]-(18883-66-4)
Sicherheit
Kennzeichnung gefährlicher: Xn,T
R-Sätze:: 40-61-46-45-22-20/21/22
S-Sätze:: 36/37-53-45-36-22
RIDADR : 3249
WGK Germany : 3
RTECS-Nr.: LZ5775000
F : 3-10-21
HazardClass : 6.1(b)
PackingGroup : III
HS Code : 29419090
Giftige Stoffe Daten: 18883-66-4(Hazardous Substances Data)
Toxizität: LD50 in female mice (mg/kg): 360 i.p.; 275 i.v.; in male dogs (mg/kg): 50 i.v. (Iwasaki)

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.
Chemische Eigenschaften
off-white to pale yellow crystalline powder
Verwenden
antineoplastic, alkylating agent
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.
Verwenden
Streptozotocin is an unusual aminoglycoside containing a nitrosoamino group produced by Streptomyces achromogenes and discovered in 1959 as an antibiotic. The nitrosoamino group enables the metabolite to act as a nitric oxide (NO) donor. NO is an important messenger molecule involved in many physiological and pathological processes in the body. Streptozotocin is also widely used to induce diabetes in rodent models by inhibition of β-cell O-GlcNAcase.
Verwenden
somatostatin octapeptide analog
Definition
ChEBI: An antibiotic that is produced by Streptomyces achromogenes. It is used as an antineoplastic agent and to induce diabetes in experimental animals.
Trademarks
Zanosar (Sicor).
Allgemeine Beschreibung
Streptozocin is available in 1-g vials for IV administrationin the treatment of metastatic islet cell carcinoma of the pancreas,colon cancer, and Hodgkin’s disease. Activation resultsin the formation of methyl carbonium ions, which alkylateDNA, but the agent is less effective in alkylating DNAand carbamylating proteins than other nitrosoureas, which isbecause in part of an intramolecular carbamoylation. The internalcarbamate group migration occurs via the hydroxylgroups of the glucose portion of the molecule. There is a reducedeffect on RNA function compared with other nitrosoureasas well. The hydrophilic agent is rapidly clearedfrom the plasma with an elimination half-life of 35 minutes.The presence of the glucose moiety allows for utilization ofglucose transporters, which concentrate the compound inthe -cells of the pancreas. The metabolism of the agent hasnot been well characterized. Renal toxicity is dose limitingand may present initially as proteinuria and azotemia butmay progress to renal failure. Nausea and vomiting may besevere with the agent, whereas myelosuppression is generallymild. Normal glucose metabolism may be altered sothat hypoglycemia or hyperglycemia may be seen. In someanimal species, streptozocin produces diabetes but muchmilder effects are seen in man.
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 .
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.
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
2-Desoxy-2-(((methylnitrosoamino)-carbonyl)amino)-D-glucopyranose Anbieter Lieferant Produzent Hersteller Vertrieb Händler.      Global( 233)Lieferanten     
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18883-66-4(2-Desoxy-2-(((methylnitrosoamino)-carbonyl)amino)-D-glucopyranose)Verwandte Suche:
Methyl Methylacetat Kresoxim-methyl Aminocapronsure Pyrazophos (ISO) 2-Desoxy-2-(((methylnitrosoamino)-carbonyl)amino)-D-glucopyranose Glycin Syrupe, hydrolysierte Strke- Ivermectin D-Glucose monohydrate Brommethan Centchroman Carbonylsulfid glucopyranose Parathion-methyl (ISO) Tetrahydro-4H-pyran-4-on Methylacrylat Thiophanat-methyl
STZ STREPTOZOCIN STREPTOZOTOCIN STR ZANOSAR U-9889 2-deoxy-2-(((methylnitrosoamino)carbonyl)amino)-d-glucopyranos 2-deoxy-2-(((methylnitrosoamino)carbonyl)amino)-d-glucos 2-deoxy-2-(3-methyl-3-nitrosoureido)-alpha(andbeta)-d-glucopyranose 2-deoxy-2-(3-methyl-3-nitrosoureido)-d-glucos estreptozocina nci-c03167 n-d-glucosyl(2)-n’-nitrosomethylharnstoff n-d-glucosyl-(2)-n’-nitrosomethylurea nsc-85598 nsc85998 nsc-85998 rcrawastenumberu206 streptozocine(french) streptozocinium(latin) streptozoticin strz 2-DEOXY-2-(3-METHYL-3-NITROSOUREIDO)-D-GLUCOPYRANOSE 2-DEOXY-2 [([METHYL-NITROSOAMINO]-CARBONYL)-AMINO]-D-GLUCOPYRANOSE 2-DEOXY-2-[[(METHYLNITROSOAMINO)CARBONYL]AMINO]-D-GLUCOSE STREPTOZOTOCIN MIXED ANOMERS STREPTOZOTOCIN 99.5% STREPTOZOTOCIN 99.5% BIOTECH GRADE Streptozotocin[Streptozocin] mixedanomers Streptozotocine Streptozocin (STZ) D-Glucose, 2-deoxy-2-[[(methyl-nitrosoamino)-carbonyl]amino]- 18883-66-4 18884-66-4 Glucopyranose, 2-deoxy-2-(3-methyl-3-nitrosoureido)-D- Streptozocin, N-(Methylnitrosocarbamoyl)-alpha-D-glucosamine STREPTOZOTOCIN extrapure Streptozotocin, N-(Methylnitrosocarbamoyl)-α-D-glucosamine 1-Methyl-1-nitroso-3-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]urea Streptozocin,97% 2-Desoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose STREPTOZOCIN PURE Streptozocin,N-(Methylnitrosocarbamoyl)-α-D-glucosamine, Streptozotocin 3-Methyl-3-nitroso-1-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxyMethyl)oxan-3-yl]urea STZ/Streptozotocin Streptozotocin (Zanosar) 1-Methyl-1-nitroso-3-((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxyMethyl)tetrahydro-2H-pyran-3-yl)urea STREPTOZOSIN Zanosar, NSC85998, U9889, 1006-60 Streptozotocin Streptozocin STZ Streptozotocin (STZ) Streptozocin 2-Desoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose Streptozotocin 2-Desoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose Streptozocin Vetec(TM) reagent grade, 98%, powder EZNA KIT ULTRA-PURE TOTAL RNA MIDI Streptozotocin (U-9889) N-(METHYLNITROSOCARBAMOYL)-A-D-GLUCOSAMINE
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