Structure via PubChem · Public domain (PubChem)
nelarabine
Sign in to saveAlso known as NLR506, 506U78, Arranon®, Atriance®, Nelzarabine, 2-Amino-9-beta-D-arabinofuranosyl-6-methoxy-9H-purine
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).
Chemical data
- Formula
- C11H15N5O5
- Molecular weight
- 297.27 g/mol
- IUPAC name
- (2R,3S,4S,5R)-2-(2-amino-6-methoxypurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
- SMILES
- COC1=NC(=NC2=C1N=CN2[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)O)N
- InChIKey
- IXOXBSCIXZEQEQ-UHTZMRCNSA-N
- XLogP
- -0.7
- Polar surface area
- 149 Ų
- H-bond donors
- 4
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2005
- Admin. routes
- parenteral
- Indications
- neoplasm, leukemia, T-cell acute lymphoblastic leukemia, acute lymphoblastic leukemia
via ChEMBL · EBI
Wikidata facts
- Has part
- nitrogen
- Mass
- 297.107319
- Has use
- medication
Show 7 more facts
- chemical formula
- C₁₁H₁₅N₅O₅
- isomeric SMILES
- COC1=NC(=NC2=C1N=CN2[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)O)N
- canonical SMILES
- COC1=NC(=NC2=C1N=CN2C3C(C(C(O3)CO)O)O)N
- World Health Organisation international non-proprietary name
- nelzarabine
- subject has role
- DNA polymerase inhibitors
- Commons category
- Nelarabine
- legal status (medicine)
- boxed warning
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- References
- External links
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. 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 October 2005. It is available as a generic medication.
Excerpted from Wikipedia’s “nelarabine” article, available under the CC BY-SA 4.0 licence.