Nelarabine

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Nelarabine
Clinical data
AHFS/Drugs.comMonograph
License data
Routes of
administration		Intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityn/a
Protein binding<25%
MetabolismBy adenosine deaminase, to 9-β-D-arabinofuranosylguanine
Elimination half-life30 minutes (nelarabine)
3 hours (ara-G)
ExcretionRenal
Identifiers
  • (2R,3S,4S,5R)-2-(2-amino-6-methoxy-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.170.768 Edit this at Wikidata
Chemical and physical data
FormulaC11H15N5O5
Molar mass297.268 g/mol 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 checkY
  • Key:IXOXBSCIXZEQEQ-UHTZMRCNSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Nelarabine is a chemotherapy drug used in T-cell acute lymphoblastic leukemia. It was previously known as 506U78.

Nelarabine is a prodrug of arabinosylguanine nucleotide triphosphate (araGTP), a type of purine nucleoside analog, which causes inhibition of DNA synthesis and cytotoxicity.[2] 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.[3] It was later approved in the European Union in October 2005. Complete responses have been achieved with this medication.

It is marketed in the US as Arranon and as Atriance in the EU by Novartis.[4]

References

  1. ^ "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.
  2. ^ "Nelarabine". Guide to Pharmacology. IUPHAR/BPS. Retrieved 21 August 2015.
  3. ^ Cohen, M. H.; Johnson, J. R.; Justice, R; Pazdur, R (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.
  4. ^ http://www.novartisoncology.com/products/atriance.jsp


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