TROXACITABINE

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 537

Conditions

Condition	Modality	Highest Phase	Product
Acute myeloid leukemia 136 Sources: http://www.docguide.com/fda-grants-orphan-drug-designation-troxatyl-troxacitabine http://www.ncbi.nlm.nih.gov/pubmed/17558697	Primary	Phase II 1132	Unknown Approved Use Unknown
Chronic myelogenous leukemia 22 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11821445	Primary	Phase II 1132	Unknown Approved Use Unknown
Renal cell carcinoma 31 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16211462 DOI: 10.1007/978-1-59745-148-2_9	Primary	Phase II 1132	Unknown Approved Use Unknown
Non-small cell lung cancer 206 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16211462 DOI: 10.1007/978-1-59745-148-2_9	Primary	Phase II 1132	Unknown Approved Use Unknown
Pancreatic cancer 97 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16211462 DOI: 10.1007/978-1-59745-148-2_9	Primary	Phase II 1132	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
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
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
eMolecules	43473320	https://orderbb.emolecules.com/search/#?query=43473320
mcule	MCULE-2688679067	https://mcule.com/MCULE-2688679067/

PubMed

Title	Date	PubMed
Action of troxacitabine on cells transduced with human cytidine deaminase cDNA.	2004	15069761
Synergistic antitumor activity of troxacitabine and camptothecin in selected human cancer cell lines.	2004 Aug	15266019
Troxacitabine and imatinib mesylate combination therapy of chronic myeloid leukaemia: preclinical evaluation.	2004 Mar	15009060
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 `Fri Dec 15 15:59:20 UTC 2023` Edited by `admin` on `Fri Dec 15 15:59:20 UTC 2023`
Record UNII	60KQZ0388Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TROXACITABINE

Official Name

English

LAMIVUDINE IMPURITY I [USP IMPURITY]

Common Name

English

(-)-ODDC

Code

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