Nelarabine (original) (raw)
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Chemical compound
Pharmaceutical compound
Nelarabine
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|---|---|
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| 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][3] US: WARNING[2]Rx-only[4] EU: Rx-only[5] |
| 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 YKey:IXOXBSCIXZEQEQ-UHTZMRCNSA-N Y |
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| NY (what is this?) (verify) |
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).[4][5]
Nelarabine is a prodrug of arabinosylguanine nucleotide triphosphate (araGTP), a type of purine nucleoside analog, which causes inhibition of DNA synthesis and cytotoxicity.[6] 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.[7] It was later approved in the European Union in October 2005.[5] It is available as a generic medication.[8]
- ^ a b "Nelarabine-Reach". Therapeutic Goods Administration (TGA). 5 June 2024. Retrieved 17 June 2024.
- ^ "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 October 2023.
- ^ "Therapeutic Goods (Poisons Standard—June 2024) Instrument 2024". Federal Register of Legislation. 30 May 2024. Retrieved 10 June 2024.
- ^ a b "Arranon- nelarabine injection". DailyMed. 11 June 2020. Retrieved 4 December 2020.
- ^ a b c "Atriance EPAR". European Medicines Agency (EMA). 20 September 2007. Retrieved 4 December 2020.
- ^ "Nelarabine". Guide to Pharmacology. IUPHAR/BPS. Retrieved 21 August 2015.
- ^ 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. S2CID 23463537.
- ^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.
- "Nelarabine". NCI Dictionary of Cancer Terms. National Cancer Institute.
- "Nelarabine". National Cancer Institute.[_permanent dead link_]