Troxacitabine

Investigational

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 Search

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

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: description was created based on several sources, including: http://www.sciencedirect.com/topics/page/Troxacitabine 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 4 Target ID: WP1925 Sources: http://www.sciencedirect.com/topics/page/Troxacitabine \| http://www.ncbi.nlm.nih.gov/pubmed/7606719	Blocker 555

Conditions

Condition	Modality	Highest Phase	Product
Acute myeloid leukemia 141 Sources: http://www.docguide.com/fda-grants-orphan-drug-designation-troxatyl-troxacitabine http://www.ncbi.nlm.nih.gov/pubmed/17558697	Primary	Phase II 1147	Unknown Approved Use Unknown
Chronic myelogenous leukemia 21 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11821445	Primary	Phase II 1147	Unknown Approved Use Unknown
Renal cell carcinoma 33 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16211462 DOI: 10.1007/978-1-59745-148-2_9	Primary	Phase II 1147	Unknown Approved Use Unknown
Non-small cell lung cancer 211 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16211462 DOI: 10.1007/978-1-59745-148-2_9	Primary	Phase II 1147	Unknown Approved Use Unknown
Pancreatic cancer 98 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16211462 DOI: 10.1007/978-1-59745-148-2_9	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1028 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12011137	12.5 mg/m² single, intravenous dose: 12.5 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		TROXACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
3306 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12011137	12.5 mg/m² single, intravenous dose: 12.5 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		TROXACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
30 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12011137	12.5 mg/m² single, intravenous dose: 12.5 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		TROXACITABINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY105630	https://www.001chemical.com/chem/search?q=DY105630
AK Scientific	Z5463	https://aksci.com/item_detail.php?cat=Z5463
Alfa Chemistry	ACM145918758	http://www.alfa-chemistry.com/search.aspx?q=ACM145918758
BLD Pharm	BD156025	http://www.bldpharm.com/search/Search.html?keyword=BD156025
BOC Sciences	145918-75-8	http://www.bocsci.com/description.asp?cas=145918-75-8
Chemspace	CSC010568831	https://chem-space.com/CSC010568831
Chemspace	CSC020617857	https://chem-space.com/CSC020617857
Chemspace	CSC055769577	https://chem-space.com/CSC055769577
eMolecules	43473320	https://orderbb.emolecules.com/search/#?query=43473320
Enamine	BBV-45383607	http://www.enaminestore.com/catalog/BBV-45383607
Enamine	BBV-77805541	http://www.enaminestore.com/catalog/BBV-77805541
Enamine	BBV-78303901	http://www.enaminestore.com/catalog/BBV-78303901
Lab Network	LN01300835	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01300835
Matrix Scientific	125360	http://www.matrixscientific.com/125360.html
mcule	MCULE-2688679067	https://mcule.com/MCULE-2688679067/
Molcore	MC105630	http://www.molcore.com/CatMC105630.html
MuseChem	R016756	https://www.musechem.com/product/R016756.html
Synthonix	15348	https://synthonix.com/catalogsearch/result/?q=15348
Tetrahedron	TS87289	http://www.thsci.com/search.do?q=TS87289
Toronto Research Chemicals	T805580	https://www.trc-canada.com/product-detail/?CatNum=T805580

PubMed

Title	Date	PubMed
Impairment of APE1 function enhances cellular sensitivity to clinically relevant alkylators and antimetabolites.	2009-06	19470598
Troxacitabine in acute leukemia.	2007-06	17558697
Evaluation of the L-stereoisomeric nucleoside analog troxacitabine for the treatment of acute myeloid leukemia.	2007-04	17371201
Population pharmacokinetics of troxacitabine, a novel dioxolane nucleoside analogue.	2006-04-01	16609029
Synergistic antitumor activity of troxacitabine and camptothecin in selected human cancer cell lines.	2004-08	15266019
Troxacitabine and imatinib mesylate combination therapy of chronic myeloid leukaemia: preclinical evaluation.	2004-03	15009060
Action of troxacitabine on cells transduced with human cytidine deaminase cDNA.	2004	15069761

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 `Mon Mar 31 18:15:30 GMT 2025` Edited by `admin` on `Mon Mar 31 18:15:30 GMT 2025`
Record UNII	60KQZ0388Y
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

(-)-ODDC

Preferred Name

English

Troxacitabine

Official Name

English

LAMIVUDINE IMPURITY I [USP IMPURITY]

Common Name

English

troxacitabine [INN]

Common Name

English

LAMIVUDINE IMPURITY I [EP IMPURITY]

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

(-)-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

TROXATYL

Brand Name

English

TROXACITABINE [MI]

Common Name

English

TROXACITABINE [USAN]

Common Name

English

BCH-4556

Code

English

Classification Tree Code System Code

FDA ORPHAN DRUG

202005

Created by admin on Mon Mar 31 18:15:30 GMT 2025 , Edited by admin on Mon Mar 31 18:15:30 GMT 2025

NCI_THESAURUS

C1557

Created by admin on Mon Mar 31 18:15:31 GMT 2025 , Edited by admin on Mon Mar 31 18:15:31 GMT 2025

EU-Orphan Drug

EU/3/05/311

Created by admin on Mon Mar 31 18:15:30 GMT 2025 , Edited by admin on Mon Mar 31 18:15:30 GMT 2025

Code System Code Type Description

INN

7886

Created by admin on Mon Mar 31 18:15:30 GMT 2025 , Edited by admin on Mon Mar 31 18:15:30 GMT 2025

PRIMARY

MESH

C074908

Created by admin on Mon Mar 31 18:15:30 GMT 2025 , Edited by admin on Mon Mar 31 18:15:30 GMT 2025

PRIMARY

PUBCHEM

454194

Created by admin on Mon Mar 31 18:15:30 GMT 2025 , Edited by admin on Mon Mar 31 18:15:30 GMT 2025

PRIMARY

USAN

KK-68

Created by admin on Mon Mar 31 18:15:31 GMT 2025 , Edited by admin on Mon Mar 31 18:15:31 GMT 2025

PRIMARY

FDA UNII

60KQZ0388Y

Created by admin on Mon Mar 31 18:15:31 GMT 2025 , Edited by admin on Mon Mar 31 18:15:31 GMT 2025

PRIMARY

WIKIPEDIA

TROXACITABINE

Created by admin on Mon Mar 31 18:15:30 GMT 2025 , Edited by admin on Mon Mar 31 18:15:30 GMT 2025

PRIMARY

DRUG CENTRAL

3635

Created by admin on Mon Mar 31 18:15:31 GMT 2025 , Edited by admin on Mon Mar 31 18:15:31 GMT 2025

PRIMARY

EPA CompTox

DTXSID2048791

Created by admin on Mon Mar 31 18:15:31 GMT 2025 , Edited by admin on Mon Mar 31 18:15:31 GMT 2025

PRIMARY

NCI_THESAURUS

C1438

Created by admin on Mon Mar 31 18:15:30 GMT 2025 , Edited by admin on Mon Mar 31 18:15:30 GMT 2025

PRIMARY

CAS

145918-75-8

Created by admin on Mon Mar 31 18:15:30 GMT 2025 , Edited by admin on Mon Mar 31 18:15:30 GMT 2025

PRIMARY

DRUG BANK

DB04961

Created by admin on Mon Mar 31 18:15:31 GMT 2025 , Edited by admin on Mon Mar 31 18:15:31 GMT 2025

PRIMARY

MERCK INDEX

m11238

Created by admin on Mon Mar 31 18:15:30 GMT 2025 , Edited by admin on Mon Mar 31 18:15:30 GMT 2025

PRIMARY

Merck Index

SMS_ID

100000088103

Created by admin on Mon Mar 31 18:15:31 GMT 2025 , Edited by admin on Mon Mar 31 18:15:31 GMT 2025

PRIMARY

EVMPD

SUB22612

Created by admin on Mon Mar 31 18:15:30 GMT 2025 , Edited by admin on Mon Mar 31 18:15:30 GMT 2025

PRIMARY

ChEMBL

CHEMBL359164

Created by admin on Mon Mar 31 18:15:30 GMT 2025 , Edited by admin on Mon Mar 31 18:15:30 GMT 2025

PRIMARY

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METABOLITE ACTIVE -> PRODRUG

Amount:

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LAMIVUDINE

PARENT -> IMPURITY

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

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TROXACITABINE TRIPHOSPHATE

ACTIVE MOIETY

Amount:

Details

SMILES

InChI

DescriptionSources: DOI: 10.1007/978-1-59745-148-2_9Curator's Comment: description was created based on several sources, including: http://www.sciencedirect.com/topics/page/Troxacitabine http://www.docguide.com/fda-grants-orphan-drug-designation-troxatyl-troxacitabine

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Approved Use

Approved Use

Cmax

AUC

T1/2

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: DOI: 10.1007/978-1-59745-148-2_9
Curator's Comment: description was created based on several sources, including: http://www.sciencedirect.com/topics/page/Troxacitabine http://www.docguide.com/fda-grants-orphan-drug-designation-troxatyl-troxacitabine

C_max

T_1/2