Nelarabine

Nelarabine

Systematic (IUPAC) name
(2R,3S,4S,5R)-2-(2-amino-6-methoxy-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Clinical data
AHFS/Drugs.com	monograph
Licence data	EMA:Link, US FDA:link
Pregnancy category	US: D (Evidence of risk)
Legal status	US: ℞-only
Routes of administration	Intravenous
Pharmacokinetic data
Bioavailability	n/a
Protein binding	<25%
Metabolism	By adenosine deaminase, to 9-β-D-arabinofuranosylguanine
Biological half-life	30 minutes (nelarabine) 3 hours (ara-G)
Excretion	Renal
Identifiers
CAS Number	121032-29-9 Y
ATC code	L01BB07 (WHO)
PubChem	CID: 3011155
IUPHAR/BPS	7090
DrugBank	DB01280 Y
ChemSpider	2280207 Y
UNII	60158CV180 Y
KEGG	D05134 N
ChEMBL	CHEMBL1201112 N
Chemical data
Formula	C11H15N5O5
Molecular mass	297.268 g/mol
SMILES n2c1c(nc(nc1OC)N)n(c2)[C@@H]3O[C@@H]([C@@H](O)[C@@H]3O)CO
InChI 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 Y Key:IXOXBSCIXZEQEQ-UHTZMRCNSA-N Y
NY (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 purine nucleoside analog converted to its corresponding arabinosylguanine nucleotide triphosphate (araGTP), resulting in inhibition of DNA synthesis and cytotoxicity. 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. It was later approved in the European Union in the October of 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.