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Details

Stereochemistry ABSOLUTE
Molecular Formula C8H11N3O4
Molecular Weight 213.191
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TROXACITABINE

SMILES

c1cn([C@]2([H])CO[C@]([H])(CO)O2)c(nc1=N)O

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 213.191
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Sources: DOI: 10.1007/978-1-59745-148-2_9
Curator's Comment:: http://www.docguide.com/fda-grants-orphan-drug-designation-troxatyl-troxacitabine

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Population pharmacokinetics of troxacitabine, a novel dioxolane nucleoside analogue.
2006 Apr 1
Evaluation of the L-stereoisomeric nucleoside analog troxacitabine for the treatment of acute myeloid leukemia.
2007 Apr
Troxacitabine in acute leukemia.
2007 Jun
Impairment of APE1 function enhances cellular sensitivity to clinically relevant alkylators and antimetabolites.
2009 Jun
Patents

Sample Use Guides

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
Created
by admin
on Sat Jun 26 03:44:21 UTC 2021
Edited
by admin
on Sat Jun 26 03:44:21 UTC 2021
Record UNII
60KQZ0388Y
Record Status Validated (UNII)
Record Version
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Name Type Language
TROXACITABINE
INN   MI   USAN   WHO-DD  
USAN   INN  
Official Name English
(-)-ODDC
Code English
TROXACITABINE [INN]
Common Name English
4-AMINO-1-((2S,4S)-2-(HYDROXYMETHYL)-1,3-DIOXOLAN-4-YL)PYRIMIDIN-2(1H)-ONE
Systematic Name English
TROXACITABINE [WHO-DD]
Common Name English
LAMIVUDINE IMPURITY I RS [USP]
Common Name English
(-)-1-((2S,4S)-2-(HYDROXYMETHYL)-1,3-DIOXOLAN-4-YL)CYTOSINE
Systematic Name English
(2S-CIS)-4-AMINO-1-(2-(HYDROXYMETHYL)-1,3-DIOXOLAN-4-YL)-2(1H)-PYRIMIDINONE
Systematic Name English
LAMIVUDINE IMPURITY I [EP]
Common Name English
TROXATYL
Brand Name English
TROXACITABINE [MI]
Common Name English
TROXACITABINE [USAN]
Common Name English
BCH-4556
Code English
LAMIVUDINE IMPURITY I [USP]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 202005
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
NCI_THESAURUS C1557
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
EU-Orphan Drug EU/3/05/311
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
Code System Code Type Description
INN
7886
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
MESH
C074908
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
PUBCHEM
454194
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
FDA UNII
60KQZ0388Y
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
WIKIPEDIA
TROXACITABINE
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
DRUG CENTRAL
3635
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
EPA CompTox
145918-75-8
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
NCI_THESAURUS
C1438
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
CAS
145918-75-8
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
DRUG BANK
DB04961
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
MERCK INDEX
M11238
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY Merck Index
EVMPD
SUB22612
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
ChEMBL
CHEMBL359164
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY