Structure via PubChem · Public domain (PubChem)
azacitidine
Sign in to saveAlso known as 5-AZAC, 5-azacytidine, ladakamycin, 4-amino-1-beta-D-ribofuranosyl-s-triazin-2(1H)-one, 5-AZC
Azacitidine, sold under the brand name Vidaza among others, is a medication used for the treatment of myelodysplastic syndrome, myeloid leukemia, and juvenile myelomonocytic leukemia. It is a chemical analog of cytidine, a nucleoside in DNA and RNA. Azacitidine and its deoxy derivative, decitabine (also known as 5-aza-2′-deoxycytidine) were first synthesized in Czechoslovakia as potential chemotherapeutic agents for cancer.
Chemical data
- Formula
- C8H12N4O5
- Molecular weight
- 244.2 g/mol
- IUPAC name
- 4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3,5-triazin-2-one
- SMILES
- C1=NC(=NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N
- InChIKey
- NMUSYJAQQFHJEW-KVTDHHQDSA-N
- XLogP
- -2.2
- Polar surface area
- 141 Ų
- H-bond donors
- 4
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2004
- Admin. routes
- oral, parenteral
- Indications
- acute myeloid leukemia, myelodysplastic syndrome, non-small cell lung carcinoma, refractory anemia with excess blasts
via ChEMBL · EBI
Research
10,090 papers- Ivosidenib and Azacitidine in IDH1-Mutated Acute Myeloid Leukemia.The New England journal of medicine · 2022
- Azacitidine.IARC monographs on the evaluation of carcinogenic risks to humans · 1990
- Azacitidine-induced pneumonitis and literature review.BMJ case reports · 2020
- Impact of Venetoclax and Azacitidine in Treatment-Naïve Patients with Acute Myeloid Leukemia and IDH1/2 Mutations.Clinical cancer research : an official journal of the American Association for Cancer Research · 2022
- 5-Azacytidine/Azacitidine.Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer · 2010
via PubMed
Wikidata facts
- Mass
- 244.081
- Has use
- medication
Show 7 more facts
- medical condition treated
- myelodysplastic syndrome
- chemical formula
- C₈H₁₂N₄O₅
- subject has role
- carcinogen
- Commons category
- Azacitidine
- canonical SMILES
- C1=NC(=NC(=O)N1C2C(C(C(O2)CO)O)O)N
- isomeric SMILES
- C1=NC(=NC(=O)N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N
- stylized name
- azaCITIDine
Sources (7)
via Wikidata · CC0
~8 min read
Encyclopedic overview
8 sectionsContents
- Medical uses
- Mechanism of action
- Inhibition of methylation
- Toxicity
- History
- Research
- References
- External links
Azacitidine, sold under the brand name Vidaza among others, is a medication used for the treatment of myelodysplastic syndrome, myeloid leukemia, and juvenile myelomonocytic leukemia. It is a chemical analog of cytidine, a nucleoside in DNA and RNA. Azacitidine and its deoxy derivative, decitabine (also known as 5-aza-2′-deoxycytidine) were first synthesized in Czechoslovakia as potential chemotherapeutic agents for cancer.
The most common adverse reactions in children with juvenile myelomonocytic leukemia include pyrexia, rash, upper respiratory tract infection, and anemia.
Excerpted from Wikipedia’s “azacitidine” article, available under the CC BY-SA 4.0 licence.