Streptozocin

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Cat Number

API0232388

CAS Number

18883-66-4

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Product Detail Description Scientific Support Customer Q&A

CAS Number

18883-66-4

EINECS

242-646-8

Synonyms

Streptozocinium

Molecular Formula

C8H15N3O7

Molecular Weight

265.22

Smiles

CN(C(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O)CO)O)O)N=O

Appearance

Faint yellow crystalline powder

Melting Point

121℃

General Description

Streptozocin, also known as streptozotocin, is a synthetic antineoplastic agent belonging to the nitrosourea class, chemically related to other nitrosoureas used in cancer chemotherapy. Originally isolated from Streptomyces achromogenes, streptozocin is notable for its selective toxicity toward pancreatic islet cells due to its glucose moiety, which facilitates uptake via the GLUT2 glucose transporter.

Mechanism of Action

Streptozocin exerts its cytotoxic effects primarily through alkylation of DNA, specifically by generating methylcarbonium ions that methylate guanine residues, leading to DNA strand breaks and interstrand cross-links. The drug enters cells preferentially through the GLUT2 transporter, explaining its selective toxicity toward pancreatic beta cells and islet cell tumors. This DNA damage triggers apoptosis and cell death, with the glucose moiety reducing bone marrow toxicity compared to other nitrosoureas while preserving alkylating activity.

Application

Streptozocin is indicated for the treatment of metastatic islet cell carcinoma of the pancreas, including both functional and nonfunctional tumors. Streptozocin is frequently used in combination with 5-fluorouracil or doxorubicin, as combination therapy has demonstrated superior response rates in pancreatic neuroendocrine tumors. Due to its significant renal toxicity, which is dose-related and cumulative, therapy requires close monitoring of renal function and is reserved for patients with symptomatic or progressive metastatic disease.

Rogers JE, et al. evaluated outcomes associated with FAS chemotherapy (5-fluorouracil, doxorubicin, and streptozocin) in 220 patients with advanced well-differentiated pancreatic neuroendocrine tumors (PanNETs) treated between 1992 and 2013. The regimen yielded an overall response rate of 41%, with median progression-free survival of 20 months and median overall survival of 63 months. First-line FAS therapy was associated with improved outcomes compared to later-line use. Grade ≥3 adverse events included neutropenia (10%) and nausea or vomiting (5.5%), with dose reductions required in 32% of patients. Importantly, prior exposure to FAS did not appear to compromise the subsequent efficacy of everolimus (median PFS 10 months) or temozolomide-based regimens (objective response rate 13%; median PFS 5.2 months).

Fig. 1 PFS on tem-based treatment post FAS. (Rogers JE, et al., 2022)

References

Rogers JE, et al. Fluorouracil, Doxorubicin with Streptozocin and Subsequent Therapies in Pancreatic Neuroendocrine Tumors. Neuroendocrinology. 2022;112(1):34-42.

Does Streptozocin require special storage conditions as a nitrosourea compound?

Yes, as a nitrosourea, it is thermally labile. It must be stored at 2-8°C in a freezer, protected from light, to prevent decomposition and maintain its antitumor activity.

Is Streptozocin sensitive to light during handling and storage?

Extremely. Photodegradation is a significant concern. All handling should be done under subdued light, and it must be stored in light-resistant, amber vials or foil-wrapped containers.

What is the stability of Streptozocin after reconstitution?

Reconstituted solutions are unstable and must be used within a few hours if stored at room temperature, or within 24-48 hours under refrigeration. We provide detailed stability guidelines for various diluents.

How is the purity of Streptozocin verified given its instability?

We use a rapid, stability-indicating HPLC method performed immediately upon sampling to accurately quantify the parent compound and its major degradation products before they increase.