TROXACITABINE

Investigational

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 Search

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Synthesis of DNA 3 Target ID: WP1925 Sources: http://www.sciencedirect.com/topics/page/Troxacitabine \| http://www.ncbi.nlm.nih.gov/pubmed/7606719	Blocker 504	Renal cell carcinoma Pancreatic cancer Non-small cell lung cancer Chronic myelogenous leukemia Acute myeloid leukemia

Conditions

Condition	Modality	Targets	Highest Phase
Acute myeloid leukemia 128 Sources: http://www.docguide.com/fda-grants-orphan-drug-designation-troxatyl-troxacitabine http://www.ncbi.nlm.nih.gov/pubmed/17558697	Primary	Synthesis of DNA	Phase II
Chronic myelogenous leukemia 20 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11821445	Primary	Synthesis of DNA	Phase II
Renal cell carcinoma 27 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16211462 DOI: 10.1007/978-1-59745-148-2_9	Primary	Synthesis of DNA	Phase II
Non-small cell lung cancer 195 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16211462 DOI: 10.1007/978-1-59745-148-2_9	Primary	Synthesis of DNA	Phase II
Pancreatic cancer 91 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16211462 DOI: 10.1007/978-1-59745-148-2_9	Primary	Synthesis of DNA	Phase II

PubMed

Title	Date	PubMed
Population pharmacokinetics of troxacitabine, a novel dioxolane nucleoside analogue.	2006 Apr 1	16609029
Evaluation of the L-stereoisomeric nucleoside analog troxacitabine for the treatment of acute myeloid leukemia.	2007 Apr	17371201
Troxacitabine in acute leukemia.	2007 Jun	17558697
Impairment of APE1 function enhances cellular sensitivity to clinically relevant alkylators and antimetabolites.	2009 Jun	19470598

Patents

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 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

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