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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H11N3O4
Molecular Weight 213.1906
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TROXACITABINE

SMILES

NC1=NC(=O)N(C=C1)[C@@H]2CO[C@H](CO)O2

InChI

InChIKey=RXRGZNYSEHTMHC-BQBZGAKWSA-N
InChI=1S/C8H11N3O4/c9-5-1-2-11(8(13)10-5)6-4-14-7(3-12)15-6/h1-2,6-7,12H,3-4H2,(H2,9,10,13)/t6-,7-/m0/s1

HIDE SMILES / InChI

Molecular Formula C8H11N3O4
Molecular Weight 213.1906
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Troxacitabine is a synthetic nucleoside analogue. It is a poor substrate for nucleoside transporters and gains entry into cells by passive diffusion. Intracellular conversion to its active triphosphate form is via deoxycytidine kinase. Incorporation of this metabolite into DNA results in immediate chain termination and apoptosis induction. It is the first nucleoside analog with anticancer activity that has an unnatural stereochemical configuration. The dose-limiting adverse reactions were stomatitis and hand–foot syndrome.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
1028 ng/mL
12.5 mg/m² single, intravenous
TROXACITABINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
3306 ng × h/mL
12.5 mg/m² single, intravenous
TROXACITABINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
30 h
12.5 mg/m² single, intravenous
TROXACITABINE plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
The recommended dose was defined as 8mg/m2/day over 30 minutes for 5 days.
Route of Administration: Intravenous
In Vitro Use Guide
The CCRF-CEM leukemia cell line was highly sensitive to the antiproliferative effects of troxacitabine with inhibition of proliferation by 50% observed at 160 nm.
Substance Class Chemical
Record UNII
60KQZ0388Y
Record Status Validated (UNII)
Record Version