Structure via PubChem · Public domain (PubChem)
آزاسیتیدین
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