Streptozocin
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MedKoo CAT#: 100780

CAS#: 18883-66-4

Description: Streptozocin is a methylnitrosourea antineoplastic antibiotic isolated from the bacterium Streptomyces achromogenes. Streptozocin alkylates DNA, forming inter-strand DNA cross-links and inhibiting DNA synthesis. Due to its glucose moiety, this agent is readily taken up by pancreatic beta cells, inducing diabetes mellitus at high concentrations. Unlike other nitrosoureas, streptozocin causes little myelosuppression.


Chemical Structure

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Streptozocin
CAS# 18883-66-4

Theoretical Analysis

MedKoo Cat#: 100780
Name: Streptozocin
CAS#: 18883-66-4
Chemical Formula: C8H15N3O7
Exact Mass: 265.091
Molecular Weight: 265.22
Elemental Analysis: C, 36.23; H, 5.70; N, 15.84; O, 42.23

Size Price Shipping out time Quantity
1g USD 190 Same day
2g USD 350 Same day
5g USD 750 Same day
10g USD 1250 Same day
20g USD 1850 Same day
50g USD 3950 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2021-03-05. Prices are subject to change without notice.

Streptozocin, purity > 95%, is in stock. Note: This product contains apha- and beta isomers.

Synonym: U9889; U-9889; U 9889; NCI-C03167; NSC-85998; AI3-50821; NRRL 2697; STZ; SZC; SZN; streptozotocin. US brand name: Zanosar.

IUPAC/Chemical Name: 1-methyl-1-nitroso-3-((3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)urea

InChi Key: ZSJLQEPLLKMAKR-YDEIVXIUSA-N

InChi Code: 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

SMILES Code: O=C(N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O)N(C)N=O

Appearance:
Solid powder

Purity:
>95% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO and in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO or water

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 265.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Satyam SM, Bairy LK, Pirasanthan R, Vaishnav RL. Grape seed extract and Zinc containing nutritional food supplement delays onset and progression of Streptozocin-induced diabetic cataract in Wistar rats. J Food Sci Technol. 2015 May;52(5):2824-32. doi: 10.1007/s13197-014-1305-y. Epub 2014 Mar 23. PubMed PMID: 25892780; PubMed Central PMCID: PMC4397290.

2: Lu WN, Zheng FP, Lai DW, Li H. Xuezhikang () reduced renal cell apoptosis in streptozocin-induced diabetic rats through regulation of Bcl-2 family. Chin J Integr Med. 2015 Apr 6. [Epub ahead of print] PubMed PMID: 25847779.

3: Azizi R, Goodarzi MT, Salemi Z. Effect of biochanin a on serum visfatin level of streptozocin-induced diabetic rats. Iran Red Crescent Med J. 2014 Sep 5;16(9):e15424. doi: 10.5812/ircmj.15424. eCollection 2014 Sep. PubMed PMID: 25593725; PubMed Central PMCID: PMC4270635.

4: Ducreux M, Dahan L, Smith D, O'Toole D, Lepère C, Dromain C, Vilgrain V, Baudin E, Lombard-Bohas C, Scoazec JY, Seitz JF, Bitoun L, Koné S, Mitry E. Bevacizumab combined with 5-FU/streptozocin in patients with progressive metastatic well-differentiated pancreatic endocrine tumours (BETTER trial)--a phase II non-randomised trial. Eur J Cancer. 2014 Dec;50(18):3098-106. doi: 10.1016/j.ejca.2014.10.002. Epub 2014 Oct 27. PubMed PMID: 25454412.

5: Artunc-Ulkumen B, Pala HG, Pala EE, Yavasoglu A, Yigitturk G, Erbas O. Exenatide improves ovarian and endometrial injury and preserves ovarian reserve in streptozocin induced diabetic rats. Gynecol Endocrinol. 2014 Nov 4:1-6. [Epub ahead of print] PubMed PMID: 25366063.

6: Yang C, Zhu B, Hua F. Leptin deficiency is involved in the cognitive impairment of streptozocin-induced diabetic rats undergoing cardiopulmonary bypass. Int J Clin Exp Med. 2014 Sep 15;7(9):2571-7. eCollection 2014. PubMed PMID: 25356111; PubMed Central PMCID: PMC4211761.

7: Aoki T, Kokudo N, Komoto I, Takaori K, Kimura W, Sano K, Takamoto T, Hashimoto T, Okusaka T, Morizane C, Ito T, Imamura M. Streptozocin chemotherapy for advanced/metastatic well-differentiated neuroendocrine tumors: an analysis of a multi-center survey in Japan. J Gastroenterol. 2014 Oct 28. [Epub ahead of print] PubMed PMID: 25348496.

8: Wu P, He P, Zhao S, Huang T, Lu Y, Zhang K. Effects of ursolic acid derivatives on Caco-2 cells and their alleviating role in streptozocin-induced type 2 diabetic rats. Molecules. 2014 Aug 19;19(8):12559-76. doi: 10.3390/molecules190812559. PubMed PMID: 25153871.

9: Zywert A, Szkudelska K, Szkudelski T. Inhibition of phosphodiesterase 3B in insulin-secreting cells of normal and streptozocin-nicotinamide-induced diabetic rats: implications for insulin secretion. J Physiol Pharmacol. 2014 Jun;65(3):425-33. PubMed PMID: 24930515.

10: Pirmoradi L, Mohammadi MT, Safaei A, Mesbah F, Dehghani GA. Does the relief of glucose toxicity act as a mediator in proliferative actions of vanadium on pancreatic islet beta cells in streptozocin diabetic rats? Iran Biomed J. 2014 Jul;18(3):173-80. PubMed PMID: 24842144; PubMed Central PMCID: PMC4048482.

11: Demirci B, Demir O, Dost T, Birincioglu M. Protective effect of vitamin B5 (dexpanthenol) on cardiovascular damage induced by streptozocin in rats. Bratisl Lek Listy. 2014;115(4):190-6. PubMed PMID: 24797592.

12: Wang L, Tian W, Uwais Z, Li G, Li H, Guan R, Gao Z, Xin Z. AGE-breaker ALT-711 plus insulin could restore erectile function in streptozocin-induced type 1 diabetic rats. J Sex Med. 2014 Jun;11(6):1452-62. doi: 10.1111/jsm.12533. Epub 2014 Apr 28. PubMed PMID: 24766706.

13: Meyer T, Qian W, Caplin ME, Armstrong G, Lao-Sirieix SH, Hardy R, Valle JW, Talbot DC, Cunningham D, Reed N, Shaw A, Navalkissoor S, Luong TV, Corrie PG. Capecitabine and streptozocin ± cisplatin in advanced gastroenteropancreatic neuroendocrine tumours. Eur J Cancer. 2014 Mar;50(5):902-11. doi: 10.1016/j.ejca.2013.12.011. Epub 2014 Jan 17. PubMed PMID: 24445147.

14: Guo J, Xu GX, Hou ZJ, Xu JB, Huang LY. [Effect of Lycium barbarum polysaccharides on the retinal ultrastructure of streptozocin-induced diabetic rats]. Zhongguo Zhong Xi Yi Jie He Za Zhi. 2013 Oct;33(10):1404-7. Chinese. PubMed PMID: 24432689.

15: Hwang SJ, Lee KH, Jang HH, Lee SR, Woo JS, Lee HJ, Jung KH, Kim W. Febuxostat contributes to improvement of endothelial dysfunction in an experimental model of streptozocin-induced diabetic rats. Int J Cardiol. 2014 Feb 15;171(3):e110-2. doi: 10.1016/j.ijcard.2013.12.023. Epub 2013 Dec 22. PubMed PMID: 24388547.

16: Soltani N, Nematbakhsh M, Eshraghi-Jazi F, Talebi A, Ashrafi F. Effect of oral administration of magnesium on Cisplatin-induced nephrotoxicity in normal and streptozocin-induced diabetic rats. Nephrourol Mon. 2013 Sep;5(4):884-90. doi: 10.5812/numonthly.11624. Epub 2013 Aug 20. PubMed PMID: 24350087; PubMed Central PMCID: PMC3842559.

17: El-Kamshoushi AA, Abdallah WI, Helal SF, El Azhary NM, Hassan EM. A study of the early changes of the level of calcitonin gene-related Peptide and histopathology of penises of rats with experimentally induced type I diabetes mellitus by streptozocin. Sex Med. 2013 Aug;1(1):21-9. doi: 10.1002/sm2.3. PubMed PMID: 25356283; PubMed Central PMCID: PMC4184714.

18: He S, Wang D, Lu Y, Chen Y, Jin X, Wang C, Zhao J, Ren Y, Wang L, Li H, Cheng J. Increasing glucagon secretion could antagonize the action of exogenous insulin for glycemic control in streptozocin-induced diabetic rhesus monkeys. Exp Biol Med (Maywood). 2013 Apr;238(4):385-91. doi: 10.1177/1535370213477974. PubMed PMID: 23760004.

19: Gopinath C, Ponsaerts P, Fransen E, Boeykens N, Pauwels P, Wyndaele JJ. Smooth muscle cell transplantation improves bladder contractile function in streptozocin-induced diabetic rats. Cytotherapy. 2013 Jul;15(7):869-78. doi: 10.1016/j.jcyt.2013.02.015. PubMed PMID: 23731765.

20: Sałat R, Sałat K. The application of support vector regression for prediction of the antiallodynic effect of drug combinations in the mouse model of streptozocin-induced diabetic neuropathy. Comput Methods Programs Biomed. 2013 Aug;111(2):330-7. doi: 10.1016/j.cmpb.2013.04.018. Epub 2013 May 18. PubMed PMID: 23693136.



Additional Information

 
History
Streptozotocin was originally identified in the late 1950s as an antibiotic. The drug was discovered in a strain of the soil microbe Streptomyces achromogenes by scientists at the drug company Upjohn (now part of Pfizer) in Kalamazoo, Michigan. The soil sample in which the microbe turned up had been taken from Blue Rapids, Kansas, which can therefore be considered the birthplace of streptozotocin. Upjohn filed for patent protection for the drug in August 1958 and U.S. Patent 3,027,300 was granted in March 1962. In the mid-1960s streptozotocin was found to be selectively toxic to the beta cells of the pancreatic islets, the cells that normally regulate blood glucose levels by producing the hormone insulin. This suggested the drug's use as an animal model of diabetes, and as a medical treatment for cancers of the beta cells.In the 1960s and 1970s the National Cancer Institute investigated streptozotocin's use in cancer chemotherapy. Upjohn filed for FDA approval of streptozotocin as a treatment for pancreatic islet cell cancer in November 1976, and approval was granted in July 1982. The drug was subsequently marketed as Zanosar. Streptozotocin is now marketed by the generic drug company Sicor (Teva). (The above information was directly from: http://en.wikipedia.org/wiki/ Streptozotocin ).
 
DRUG DESCRIPTION
Each vial of ZANOSAR contains 1 g of the active ingredient streptozocin 2 -deoxy - 2 -[[(methylnitrosoamino)carbonyl]amino] - α(and β) - D - glucopyranose and 220 mg citric acid anhydrous. ZANOSAR is available as a sterile, pale yellow, freeze-dried preparation for intravenous administration. The pH was adjusted with sodium hydroxide. When reconstituted as directed, the pH of the solution will be between 3.5 and 4.5. Streptozocin is a synthetic antineoplastic agent that is chemically related to other nitrosoureas used in cancer chemotherapy. Streptozocin is an ivory-colored crystalline powder with a molecular weight of 265.2. It is very soluble in water or physiological saline and is soluble in alcohol.
 
CLINICAL PHARMACOLOGY
Streptozocin inhibits DNA synthesis in bacterial and mammalian cells. In bacterial cells, a specific interaction with cytosine moieties leads to degradation of DNA. The biochemical mechanism leading to mammalian cell death has not been definitely established; streptozocin inhibits cell proliferation at a considerably lower level than that needed to inhibit precursor incorporation into DNA or to inhibit several of the enzymes involved in DNA synthesis. Although streptozocin inhibits the progression of cells into mitosis, no specific phase of the cell cycle is particularly sensitive to its lethal effects. Streptozocin is active in the L1210 leukemic mouse over a fairly wide range of parenteral dosage schedules. In experiments in many animal species, streptozocin induced a diabetes that resembles human hyperglycemic nonketotic diabetes mellitus. This phenomenon, which has been extensively studied, appears to be mediated through a lowering of beta cell nicotinamide adenine dinucleotide (NAD) and consequent histopathologic alteration of pancreatic islet beta cells. The metabolism and the chemical dissociation of streptozocin that occurs under physiologic conditions has not been extensively studied. When administered intravenously to a variety of experimental animals, streptozocin disappears from the blood very rapidly. In all species tested, it was found to concentrate in the liver and kidney. As much as 20% of the drug (or metabolites containing an N-nitrosourea group) is metabolized and/or excreted by the kidney. Metabolic products have not yet been identified.