U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C8H14N3O13P3
Molecular Weight 453.1303
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TROXACITABINE TRIPHOSPHATE

SMILES

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

InChI

InChIKey=WNZKNPIDEYYOOQ-BQBZGAKWSA-N
InChI=1S/C8H14N3O13P3/c9-5-1-2-11(8(12)10-5)6-3-20-7(22-6)4-21-26(16,17)24-27(18,19)23-25(13,14)15/h1-2,6-7H,3-4H2,(H,16,17)(H,18,19)(H2,9,10,12)(H2,13,14,15)/t6-,7-/m0/s1

HIDE SMILES / InChI

Molecular Formula C8H14N3O13P3
Molecular Weight 453.1303
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sources: http://www.ncbi.nlm.nih.gov/pubmed/16211462 DOI: 10.1007/978-1-59745-148-2_9
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1028 ng/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
3306 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
30 h
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
PubMed

PubMed

TitleDatePubMed
Synergistic antitumor activity of troxacitabine and camptothecin in selected human cancer cell lines.
2004 Aug
Population pharmacokinetics of troxacitabine, a novel dioxolane nucleoside analogue.
2006 Apr 1
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 Dec 16 15:55:43 GMT 2023
Edited
by admin
on Sat Dec 16 15:55:43 GMT 2023
Record UNII
4YF9V91KCR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TROXACITABINE TRIPHOSPHATE
Common Name English
TRIPHOSPHORIC ACID, P-(((2S,4S)-4-(4-AMINO-2-OXO-1(2H)-PYRIMIDINYL)-1,3-DIOXOLAN-2-YL)METHYL) ESTER
Systematic Name English
Code System Code Type Description
PUBCHEM
503022
Created by admin on Sat Dec 16 15:55:43 GMT 2023 , Edited by admin on Sat Dec 16 15:55:43 GMT 2023
PRIMARY
CAS
171039-00-2
Created by admin on Sat Dec 16 15:55:43 GMT 2023 , Edited by admin on Sat Dec 16 15:55:43 GMT 2023
PRIMARY
FDA UNII
4YF9V91KCR
Created by admin on Sat Dec 16 15:55:43 GMT 2023 , Edited by admin on Sat Dec 16 15:55:43 GMT 2023
PRIMARY
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY