Decitabine

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Cat Number

API2353335

CAS Number

2353-33-5

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Product Detail Description Scientific Support Customer Q&A

CAS Number

2353-33-5

EINECS

219-089-4

Storage

Store at 2-8°C

Synonyms

5-Azadeoxycytidine; 2'-Deoxy-5-azacytidine; 5-Aza-deoxycytidine; Decitabina; 5-AZAdC; NSC 127716; 2-Desoxy-5-azacytidine; DTXSID7030432

Molecular Formula

C8H12N4O4

Molecular Weight

228.21

Smiles

C1[C@@H]([C@H](O[C@H]1N2C=NC(=NC2=O)N)CO)O

Appearance

White to off-white powder

Melting Point

~200°C (dec.)

Boiling Point

485.8±55.0°C at 760 mmHg

Relative Density

1.9±0.1

General Description

Decitabine is a cytidine nucleoside analogue containing a 2′‑deoxy‑5‑azacytidine structure, acting as a specific DNA methyltransferase inhibitor. The molecule substitutes a nitrogen atom for carbon at the 5‑position of the pyrimidine ring, which allows it to form covalent adducts with methyltransferase enzymes. It is the 5‑aza‑2′‑deoxycytidine isomer and is more potent than its ribonucleoside counterpart, azacitidine.

Mechanism of Action

Decitabine is incorporated into DNA during the S‑phase of the cell cycle. Once incorporated, it irreversibly traps DNA methyltransferase 1 (DNMT1) by forming a covalent complex between the enzyme and the 5‑aza‑cytosine base. This depletes functional DNMT1, leading to passive DNA demethylation after subsequent rounds of replication. The resultant reactivation of tumor suppressor genes and induction of differentiation is the basis for its antineoplastic activity.

Application

Decitabine is indicated for the treatment of myelodysplastic syndromes (MDS), including all French‑American‑British subtypes, and for acute myeloid leukemia (AML) in elderly patients unfit for intensive chemotherapy. It also demonstrates activity in chronic myelomonocytic leukemia (CMML).

This phase II study evaluated the fully oral combination of ASTX727 (oral decitabine/cedazuridine) plus venetoclax in 62 patients with acute myeloid leukemia (49 frontline, 13 relapsed/refractory). The overall response rate was 64% (95% CI 49‑77) in the frontline cohort and 46% (19‑75) in the relapsed/refractory cohort. Common grade ≥3 adverse events included febrile neutropenia (18%) and pneumonia (13%). Three deaths in remission were potentially treatment‑related. The regimen is active and safe in older or unfit patients, warranting larger confirmatory studies.

Fig. 1 Trial profile *Patients were treated with decitabine (35 mg) and cedazuridine (100 mg) on day 1–5 plus venetoclax 100 mg on day 1, 200 mg on day 2, then 400 mg on day 3–21 or 28. (Bazinet A, et al., 2024)

References

Bazinet A, et al. Oral decitabine and cedazuridine plus venetoclax for older or unfit patients with acute myeloid leukaemia: a phase 2 study. Lancet Haematol. 2024;11(4):e276-e286.

Does Decitabine require strict cold chain storage as a nucleoside analog?

Yes, it must be stored at 2-8°C. At room temperature, rapid degradation via deamination and ring-opening occurs, leading to loss of potency.

Is Decitabine sensitive to light during handling and storage?

Yes, it is highly photosensitive. Store in light-resistant containers and handle under subdued light to prevent photodegradation of the cytidine ring.

What is the stability of Decitabine after reconstitution for intravenous infusion?

Reconstituted solutions are very unstable (typically 2-4 hours at room temperature). Use immediately after preparation.

How is the impurity 5-azacytosine (a major degradation product) monitored?

This degradation product is specifically quantified using a stability-indicating HPLC method, ensuring it remains within ICH qualification thresholds.