Nelarabine

{{Short description|Chemical compound}}

{{Use dmy dates|date=August 2024}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 461742367

| image = Nelarabine structure.svg

| width = 200

| alt =

| image2 = Nelarabine ball-and-stick.png

| alt2 =

| tradename = Arranon, Atriance

| Drugs.com = {{drugs.com|monograph|nelarabine}}

| MedlinePlus = a607077

| DailyMedID = Nelarabine

| pregnancy_AU = D

| pregnancy_AU_comment =

| pregnancy_category=

| routes_of_administration = Intravenous

| ATC_prefix = L01

| ATC_suffix = BB07

| legal_AU = S4

| legal_AU_comment = {{cite web | title=Nelarabine-Reach | website=Therapeutic Goods Administration (TGA) | date=5 June 2024 | url=https://www.tga.gov.au/resources/auspmd/nelarabine-reach | access-date=17 June 2024}}{{cite web | title=Therapeutic Goods (Poisons Standard—June 2024) Instrument 2024 | website=Federal Register of Legislation | date=30 May 2024 | url=https://www.legislation.gov.au/F2024L00589/asmade/text | access-date=10 June 2024}}

| legal_BR =

| legal_BR_comment =

| legal_CA =

| legal_CA_comment =

| legal_DE =

| legal_DE_comment =

| legal_NZ =

| legal_NZ_comment =

| legal_UK =

| legal_UK_comment =

| legal_US = Rx-only

| legal_US_comment = {{cite web | title=Arranon- nelarabine injection | website=DailyMed | date=11 June 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=fffa5d75-0dba-4ad7-a252-5f60fa28489a | access-date=4 December 2020}}

| legal_EU = Rx-only

| legal_EU_comment = {{cite web | title=Atriance EPAR | website=European Medicines Agency (EMA) | date=20 September 2007 | url=https://www.ema.europa.eu/en/medicines/human/EPAR/atriance | access-date=4 December 2020}}

| legal_UN =

| legal_UN_comment =

| legal_status =

| bioavailability = n/a

| protein_bound = <25%

| metabolism = By adenosine deaminase, to 9-β-D-arabinofuranosylguanine

| elimination_half-life = 30 minutes (nelarabine)
3 hours (ara-G)

| excretion = Kidney

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 121032-29-9

| PubChem = 3011155

| IUPHAR_ligand = 7090

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01280

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 2280207

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 60158CV180

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = D05134

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1201112

| synonyms = 506U78

| C=11 | H=15 | N=5 | O=5

| smiles = n2c1c(nc(nc1OC)N)n(c2)[C@@H]3O[C@@H]([C@@H](O)[C@@H]3O)CO

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = IXOXBSCIXZEQEQ-UHTZMRCNSA-N

}}

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).

Nelarabine is a prodrug of arabinosylguanine nucleotide triphosphate (araGTP), a type of purine nucleoside analog, which causes inhibition of DNA synthesis and cytotoxicity.{{cite web |url= http://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=7090 |title= Nelarabine|website= Guide to Pharmacology|publisher= IUPHAR/BPS |access-date= 21 August 2015 }} 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.{{cite journal | vauthors = Cohen MH, Johnson JR, Justice R, Pazdur R | title = FDA drug approval summary: nelarabine (Arranon) for the treatment of T-cell lymphoblastic leukemia/lymphoma | journal = The Oncologist | volume = 13 | issue = 6 | pages = 709–14 | date = June 2008 | pmid = 18586926 | doi = 10.1634/theoncologist.2006-0017 | s2cid = 23463537 | doi-access = free }} It was later approved in the European Union in October 2005. It is available as a generic medication.{{cite web | title=Competitive Generic Therapy Approvals | website=U.S. Food and Drug Administration (FDA) | date=29 June 2023 | url=https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | access-date=29 June 2023 | archive-date=29 June 2023 | archive-url=https://web.archive.org/web/20230629233651/https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | url-status=live }}