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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H15N5O5
Molecular Weight 297.2673
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NELARABINE

SMILES

COC1=NC(N)=NC2=C1N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O

InChI

InChIKey=IXOXBSCIXZEQEQ-UHTZMRCNSA-N
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

HIDE SMILES / InChI

Molecular Formula C11H15N5O5
Molecular Weight 297.2673
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Arranon is a nucleoside metabolic inhibitor indicated for the treatment of patients with T-cell acute lymphoblastic leukemia and T-cell lymphoblastic lymphoma. It is a purine nucleoside analog converted to its corresponding arabinosylguanine nucleotide triphosphate (araGTP), resulting in inhibition of DNA synthesis and cytotoxicity. Administration of nelarabine in combination with adenosine deaminase inhibitors, such 195 as pentostatin, is not recommended. The most common (≥20%) adverse reactions were: anemia, thrombocytopenia, neutropenia, nausea, diarrhea, vomiting, constipation, fatigue, pyrexia, cough, and dyspnea

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ARRANON

Cmax

ValueDoseCo-administeredAnalytePopulation
52 μM
35 mg/kg single, intravenous
NELARABINE blood
Macaca mulatta

AUC

ValueDoseCo-administeredAnalytePopulation
2820 μM × min
35 mg/kg single, intravenous
NELARABINE blood
Macaca mulatta

T1/2

ValueDoseCo-administeredAnalytePopulation
25 min
35 mg/kg single, intravenous
NELARABINE blood
Macaca mulatta
16.5 min
75 mg/kg 2 times / hour multiple, intravenous
NELARABINE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Adult: 1,500 mg/m² over 2 hours on Days 1, 3, and 5 repeated every 21 days Pediatric: 650 mg/m² over 1 hour daily for 5 consecutive days repeated every 21 days
Route of Administration: Intravenous
In Vitro Use Guide
The in vitro efficacy of nelarabine was assessed in a panel of acute lymphoblastic leukaemia (ALL) cell lines. IC50 values were 0.067-2.15 uM.
Substance Class Chemical
Record UNII
60158CV180
Record Status Validated (UNII)
Record Version