Nelarabine

Last updated
Nelarabine
Nelarabine structure.svg
Nelarabine ball-and-stick.png
Clinical data
Trade names Arranon, Atriance
Other names506U78
AHFS/Drugs.com Monograph
MedlinePlus a607077
License data
Pregnancy
category
Routes of
administration 		Intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability n/a
Protein binding <25%
Metabolism By adenosine deaminase, to 9-β-D-arabinofuranosylguanine
Elimination half-life 30 minutes (nelarabine)
3 hours (ara-G)
Excretion Kidney
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.170.768 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H15N5O5
Molar mass 297.271 g·mol−1
3D model (JSmol)
  • n2c1c(nc(nc1OC)N)n(c2)[C@@H]3O[C@@H]([C@@H](O)[C@@H]3O)CO
  • InChI=1S/C11H15N5O5/c1-20-9-5-8(14-11(12)15-9)16(3-13-5)10-7(19)6(18)4(2-17)21-10/h3-4,6-7,10,17-19H,2H2,1H3,(H2,12,14,15)/t4-,6-,7+,10-/m1/s1 Yes check.svgY
  • Key:IXOXBSCIXZEQEQ-UHTZMRCNSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Nelarabine, sold under the brand names Arranon (US) and Atriance (EU), is a chemotherapy medication used for the treatment of T-cell acute lymphoblastic leukemia (T-ALL) and T-cell lymphoblastic lymphoma (T-LBL). [4] [5]

Nelarabine is a prodrug of arabinosylguanine nucleotide triphosphate (araGTP), a type of purine nucleoside analog, which causes inhibition of DNA synthesis and cytotoxicity. [6] Pre-clinical studies suggest that T-cells are particularly sensitive to nelarabine. In October 2005, it was approved by the FDA for acute lymphoblastic leukemia and T-cell lymphoblastic lymphoma that has not responded to or has relapsed following treatment with at least two chemotherapy regimens. [7] It was later approved in the European Union in October 2005. [5] It is available as a generic medication. [8]

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References

  1. 1 2 "Nelarabine-Reach". Therapeutic Goods Administration (TGA). 5 June 2024. Retrieved 17 June 2024.
  2. ↑ "Therapeutic Goods (Poisons Standard—June 2024) Instrument 2024". Federal Register of Legislation. 30 May 2024. Retrieved 10 June 2024.
  3. ↑ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA . Retrieved 22 Oct 2023.
  4. 1 2 "Arranon- nelarabine injection". DailyMed. 11 June 2020. Retrieved 4 December 2020.
  5. 1 2 3 "Atriance EPAR". European Medicines Agency (EMA). 20 September 2007. Retrieved 4 December 2020.
  6. ↑ "Nelarabine". Guide to Pharmacology. IUPHAR/BPS. Retrieved 21 August 2015.
  7. ↑ Cohen MH, Johnson JR, Justice R, Pazdur R (June 2008). "FDA drug approval summary: nelarabine (Arranon) for the treatment of T-cell lymphoblastic leukemia/lymphoma". The Oncologist. 13 (6): 709–14. doi: 10.1634/theoncologist.2006-0017 . PMID   18586926. S2CID   23463537.
  8. ↑ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.
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