Nelarabine

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

Nelarabine

Clinical data
AHFS/Drugs.com	Monograph
License data	EU EMA: by INN US FDA: Nelarabine
Pregnancy category	US: D (Evidence of risk)
Routes of administration	Intravenous
ATC code	L01BB07 (WHO)
Legal status
Legal status	US: ℞-only
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	Renal
Identifiers
IUPAC name (2R,3S,4S,5R)-2-(2-amino-6-methoxy-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
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.[1] 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.[2] 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.[3]

References

1. "Nelarabine". Guide to Pharmacology. IUPHAR/BPS. Retrieved 21 August 2015.
2. 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.
3. "Atriance". Novartis Oncology.