Nelarabine

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).^[3][4]

Nelarabine

Clinical data
Trade names	Arranon, Atriance
Other names	506U78
AHFS/Drugs.com	Monograph
MedlinePlus	a607077
License data	US DailyMed: Nelarabine
Pregnancy category	AU: D[1]
Routes of administration	Intravenous
ATC code	L01BB07 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)[1][2] US: ℞-only[3] EU: Rx-only[4]
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	121032-29-9 Y
PubChem CID	3011155
IUPHAR/BPS	7090
DrugBank	DB01280 Y
ChemSpider	2280207 Y
UNII	60158CV180
KEGG	D05134 N
ChEMBL	ChEMBL1201112 N
CompTox Dashboard (EPA)	DTXSID6046842
ECHA InfoCard	100.170.768
Chemical and physical data
Formula	C11H15N5O5
Molar mass	297.271 g·mol−1
3D model (JSmol)	Interactive image
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 prodrug of arabinosylguanine nucleotide triphosphate (araGTP), a type of purine nucleoside analog, which causes inhibition of DNA synthesis and cytotoxicity.^[5] 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.^[6] It was later approved in the European Union in October 2005.^[4] It is available as a generic medication.^[7]