Chemical Property of D-Glucose, 2-deoxy-2-[[(methylnitrosoamino)-carbonyl]amino]-
Chemical Property:
- Appearance/Colour:off-white to pale yellow crystalline powder
- Melting Point:121 °C (dec.)(lit.)
- Refractive Index:1.67
- Boiling Point:408.44°C (rough estimate)
- PKA:pKa 1.3 (Uncertain)
- PSA：151.92000
- Density:1.86 g/cm3
- LogP:-2.50000
- Storage Temp.:−20°C
- Sensitive.:Hygroscopic
- Solubility.:Soluble in DMSO (up to 25 mg/ml) or in Water (up to 25 mg/ml)
- Water Solubility.:soluble
- XLogP3:-1.4
- Hydrogen Bond Donor Count:5
- Hydrogen Bond Acceptor Count:8
- Rotatable Bond Count:2
- Exact Mass:265.09099983
- Heavy Atom Count:18
- Complexity:315
- Transport DOT Label:Class 9
- Purity/Quality:
-
99.0%Min *data from raw suppliers
Streptozotocin *data from reagent suppliers
Safty Information:
- Pictogram(s):
Xn,
T
- Hazard Codes:Xn,T
- Statements:
40-61-46-45-22-20/21/22
- Safety Statements:
36/37-53-45-36-22
- MSDS Files:
-
SDS file from LookChem
Total 1 MSDS from other Authors
Useful:
- Chemical Classes:Biological Agents -> Bacterial Toxins
- Drug Classes:Antineoplastic Agents
- Canonical SMILES:CN(C(=O)NC1C(C(C(OC1O)CO)O)O)N=O
- Recent ClinicalTrials:Two Chemotherapy Regimens Plus or Minus Bevacizumab
- Recent EU Clinical Trials:Randomized open label study to compare the efficacy and safety of everolimus followed by chemotherapy with STZ-5FU upon progression or the reverse sequence, chemotherapy with STZ-5FU followed by everolimus upon progression, in advanced progressive pNETs (SEQTOR study)
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Uses
It is a compound containing N-nitroso ,it acts as a nitric oxide donor in pancreatic islets ; it can induce the death of diabetic animal model style of insulin-secreting cells . Efficient DNA methylation agent, can induce chromosome breakage.it has cell toxicity On the neuroendocrine tumor cell lines with the expression of GLUT2 glucose transporter (GLUT2 glucose transporter) . Streptozocin is used for inducing Type 1 diabetes in Medical researches . antineoplastic, alkylating agent 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. 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. somatostatin octapeptide analog
-
Description
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.
-
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.
-
Therapeutic Function
Antineoplastic
-
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.
