Azacitidine

Azacitidine
Clinical data
Trade namesVidaza, Azadine, Onureg
Other names5-Azacytidine, Azacytidine, Ladakamycin, 4-Amino-1-β-D-ribofuranosyl-s-triazin-2(1H)-one, U-18496, CC-486
AHFS/Drugs.comMonograph
MedlinePlusa607068
License data
Pregnancy
category
  • AU: X (High risk)[1]
Routes of
administration		Subcutaneous, intravenous, by mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life4 hr.[8]
Identifiers
IUPAC name
  • 4-Amino-1-β-D-ribofuranosyl-1,3,5-triazin-2(1H)-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.711
Chemical and physical data
FormulaC8H12N4O5
Molar mass244.207 g·mol−1
3D model (JSmol)
SMILES
  • O=C1/N=C(\N=C/N1[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO)N
InChI
  • InChI=1S/C8H12N4O5/c9-7-10-2-12(8(16)11-7)6-5(15)4(14)3(1-13)17-6/h2-6,13-15H,1H2,(H2,9,11,16)/t3-,4-,5-,6-/m1/s1 Y
  • Key:NMUSYJAQQFHJEW-KVTDHHQDSA-N Y
  (verify)

Azacitidine, sold under the brand name Vidaza among others, is a medication used for the treatment of myelodysplastic syndrome, myeloid leukemia,[5][6] and juvenile myelomonocytic leukemia.[4][9] 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.[10]

The most common adverse reactions in children with juvenile myelomonocytic leukemia include pyrexia, rash, upper respiratory tract infection, and anemia.[9]

  1. ^ "Azacitidine (Vidaza) Use During Pregnancy". Drugs.com. 5 May 2020. Retrieved 12 August 2020.
  2. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  3. ^ "Health product highlights 2021: Annexes of products approved in 2021". Health Canada. 3 August 2022. Retrieved 25 March 2024.
  4. ^ a b Cite error: The named reference Vidaza FDA label was invoked but never defined (see the help page).
  5. ^ a b "Onureg- azacitidine tablet, film coated". DailyMed. 20 May 2021. Retrieved 24 May 2022.
  6. ^ a b "Onureg EPAR". European Medicines Agency. 20 April 2021. Retrieved 6 September 2021.
  7. ^ "Onureg Product information". Union Register of medicinal products. Retrieved 3 March 2023.
  8. ^ Vallerand AH, Deglin JH (2009). Davis's drug guide for nurses. Philadelphia: F.A. Davis Company. pp. 204–206. ISBN 978-0-8036-1912-8.
  9. ^ a b "FDA approves azacitidine". U.S. Food and Drug Administration. 20 May 2022. Archived from the original on 20 May 2022. Retrieved 24 May 2022. This article incorporates text from this source, which is in the public domain.
  10. ^ Cihák A (1974). "Biological effects of 5-azacytidine in eukaryotes". Oncology. 30 (5): 405–22. doi:10.1159/000224981. PMID 4142650.
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