Azacitidine

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Cat Number

API0232320

CAS Number

320-67-2

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Product Detail Description Scientific Support Customer Q&A

CAS Number

320-67-2

EINECS

206-280-2

Synonyms

5-azacytidine, Ladakamycin

Molecular Weight

244.2

Smiles

C1=NC(=NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N

Appearance

White crystalline powder

Melting Point

226-232℃

Boiling Point

534.5℃

General Description

Azacitidine is a pyrimidine nucleoside analogue of cytidine, classified as a nucleoside metabolic inhibitor with antineoplastic activity. It was initially FDA-approved in 2004 for adult myelodysplastic syndromes and subsequently approved for pediatric juvenile myelomonocytic leukemia in 2022.

Mechanism of Action

Azacitidine exerts its antineoplastic effects through two primary mechanisms: DNA hypomethylation and direct cytotoxicity. At low doses, it incorporates into DNA and inhibits DNA methyltransferase, causing hypomethylation that may restore normal function to genes critical for differentiation and proliferation. At higher doses, it incorporates into RNA, disrupting RNA metabolism and protein synthesis, leading to death of rapidly dividing abnormal hematopoietic cells while non-proliferating cells remain relatively insensitive.

Application

Azacitidine is indicated for adult patients with myelodysplastic syndrome subtypes including refractory anemia, refractory anemia with excess blasts, and chronic myelomonocytic leukemia. It is also indicated for pediatric patients aged one month and older with newly diagnosed juvenile myelomonocytic leukemia.

DiNardo CD, et al. evaluated the safety and efficacy of the BCL-2 inhibitor venetoclax combined with hypomethylating agents (decitabine or azacitidine) in 145 treatment-naive elderly patients with acute myeloid leukemia (AML) ineligible for intensive chemotherapy. The combination was well tolerated, with common adverse events including nausea, diarrhea, and febrile neutropenia, and no cases of tumor lysis syndrome were observed. The overall complete remission (CR) plus CR with incomplete count recovery (CRi) rate was 67%, increasing to 73% in the venetoclax 400 mg cohort. Responses were durable (median duration 11.3 months) and observed across poor-risk subgroups, including patients with adverse cytogenetics (60% CR/CRi) and those aged ≥75 years (65% CR/CRi).

Fig. 1 Duration of CR + CRi by venetoclax dose levels (dose escalation + dose expansion cohorts). (DiNardo CD, et al., 2019)

References

DiNardo CD, et al. Venetoclax combined with decitabine or azacitidine in treatment-naive, elderly patients with acute myeloid leukemia. Blood. 2019;133(1):7-17.

Does Azacitidine require strict cold chain shipping?

Yes, it is thermally labile and must be shipped and stored at 2-8°C. We use validated cold chain packaging with temperature data loggers for every shipment.

Is Azacitidine susceptible to hydrolysis in aqueous environments?

Extremely. In solution, it hydrolyzes rapidly. It is supplied as a lyophilized powder and must be reconstituted immediately before use.

What is the degradation pathway of Azacitidine under improper storage conditions?

Ring hydrolysis of the triazine ring is the primary pathway, leading to N-(formylamidino)-N'-ribofuranosylurea.

Can Azacitidine be stored in standard pharmacy refrigerators?

Yes, as long as the temperature is consistently maintained between 2-8°C. We recommend using calibrated temperature monitoring devices to ensure no deviation occurs.