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

Streptozotocin Struktur
18883-66-4
CAS-Nr.
18883-66-4
Bezeichnung:
2-Desoxy-2-(((methylnitrosoamino)-carbonyl)amino)-D-glucopyranose
Englisch Name:
Streptozotocin
Synonyma:
STZ;STREPTOZOCIN;STR;ZANOSAR;strz;U-9889;nsc85998;nsc-85598;nsc-85998;nci-c03167
CBNumber:
CB1476758
Summenformel:
C8H15N3O7
Molgewicht:
265.22
MOL-Datei:
18883-66-4.mol

2-Desoxy-2-(((methylnitrosoamino)-carbonyl)amino)-D-glucopyranose 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
L?slichkeit
Soluble in DMSO (up to 25 mg/ml) or in Water (up to 25 mg/ml)
Aggregatzustand
powder
pka
pKa 1.3 (Uncertain)
Farbe
white to light yellow
Wasserl?slichkeit
soluble
Sensitive 
Hygroscopic
Merck 
13,8912
BRN 
2060675
Stabilit?t:
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.
InChIKey
ZSJLQEPLLKMAKR-FEQHFJGESA-N
CAS Datenbank
18883-66-4
IARC
2B (Vol. 17, Sup 7) 1987
EPA chemische Informationen
Streptozotocin (18883-66-4)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher Xn,T
R-S?tze: 40-61-46-45-22-20/21/22
S-S?tze: 36/37-53-45-36-22
RIDADR  3249
WGK Germany  3
RTECS-Nr. LZ5775000
3-10-21
HazardClass  6.1(b)
PackingGroup  III
HS Code  29419090
Giftige Stoffe Daten 18883-66-4(Hazardous Substances Data)
Toxizit?t LD50 in female mice (mg/kg): 360 i.p.; 275 i.v.; in male dogs (mg/kg): 50 i.v. (Iwasaki)
Bildanzeige (GHS) GHS hazard pictogramsGHS hazard pictograms
Alarmwort Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H228 Entzündbarer Feststoff. Entzündbare Feststoffe Kategorie 1 Achtung
Warnung
GHS hazard pictogramssrc="/GHS02.jpg" width="20" height="20" /> P210, P240,P241, P280, P370+P378
H341 Kann vermutlich genetische Defekte verursachen. Keimzellmutagenit?t Kategorie 2 Warnung P201,P202, P281, P308+P313, P405,P501
H351 Kann vermutlich Krebs verursachen. Karzinogenit?t Kategorie 2 Warnung P201, P202, P281, P308+P313, P405,P501
Sicherheit
P201 Vor Gebrauch besondere Anweisungen einholen.
P202 Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.
P210 Von Hitze, hei?en Oberfl?chen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.
P240 Beh?lter und zu befüllende Anlage erden.
P241 Explosionsgeschützte [elektrische/Lüftungs-/ Beleuchtungs-/...] Ger?te verwenden.
P308+P313 BEI Exposition oder falls betroffen: ?rztlichen Rat einholen/?rztliche Hilfe hinzuziehen.

2-Desoxy-2-(((methylnitrosoamino)-carbonyl)amino)-D-glucopyranose Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R40:Verdacht auf krebserzeugende Wirkung.
R61:Kann das Kind im Mutterleib sch?digen.
R46:Kann vererbbare Sch?den verursachen.
R45:Kann Krebs erzeugen.
R22:Gesundheitssch?dlich beim Verschlucken.
R20/21/22:Gesundheitssch?dlich beim Einatmen,Verschlucken und Berührung mit der Haut.

S-S?tze 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 m?glich, 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.

Reaktivit?t 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 Aktivit?t

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.

l?uterung 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 H?ndler.

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18883-66-4(2-Desoxy-2-(((methylnitrosoamino)-carbonyl)amino)-D-glucopyranose)Verwandte Suche:


  • N-(METHYLNITROSOCARBAMOYL)-A-D-GLUCOSAMINE
  • N-(METHYLNITROSOCARBAMOYL)-ALPHA-D-GLUCOSAMINE
  • N-(METHYLNITROSOCARBAMOYL)-ALPHA-GLUCOSAMINE
  • STREPTOZOTOCIN
  • 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
  • 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
  • STREPTOZOTOCIN MIXED ANOMERS
  • STREPTOZOTOCIN 99.5%
  • STREPTOZOTOCIN 99.5% BIOTECH GRADE
  • mixedanomers
  • Streptozotocine
  • Streptozocin (STZ)
  • D-Glucose, 2-deoxy-2-[[(methyl-nitrosoamino)-carbonyl]amino]-
  • EZNA KIT ULTRA-PURE TOTAL RNA MIDI
  • 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
  • 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
  • STREPTOZOCIN PURE
  • Streptozotocin (U-9889)
  • Streptozocin,N-(Methylnitrosocarbamoyl)-α-D-glucosamine, Streptozotocin
  • Zanosar, NSC85998, U9889, 1006-60
  • Streptozotocin (STZ)
  • Streptozocin 2-Desoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose
  • Streptozotocin 2-Desoxy-2-(3-methyl-3-nitrosoureido)-D-glucopyranose
  • Streptozotocin Streptozocin STZ
  • Streptozocin Vetec(TM) reagent grade, 98%, powder
  • Streptozotocin USP/EP/BP
  • Streptozotocin (STZ) extrapure, 98%
  • Streptozotocin (STZ) for cell culture, 98%, Endotoxin (BET) 0.05EU/mg
  • beta-dimethylacrylshikonin
  • Streptozotocin[Streptozocin]
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