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
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
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 |
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
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: WP1925 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Sources: http://www.ncbi.nlm.nih.gov/pubmed/16211462 DOI: 10.1007/978-1-59745-148-2_9 |
Primary | Unknown Approved UseUnknown |
||
Sources: http://www.ncbi.nlm.nih.gov/pubmed/16211462 DOI: 10.1007/978-1-59745-148-2_9 |
Primary | Unknown Approved UseUnknown |
||
Sources: http://www.ncbi.nlm.nih.gov/pubmed/16211462 DOI: 10.1007/978-1-59745-148-2_9 |
Primary | Unknown Approved UseUnknown |
Cmax
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 |
T1/2
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 |
PubMed
Title | Date | PubMed |
---|---|---|
Action of troxacitabine on cells transduced with human cytidine deaminase cDNA. | 2004 |
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Synergistic antitumor activity of troxacitabine and camptothecin in selected human cancer cell lines. | 2004 Aug |
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Troxacitabine and imatinib mesylate combination therapy of chronic myeloid leukaemia: preclinical evaluation. | 2004 Mar |
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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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/11585758
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
Edited
Sat Jun 26 03:44:21 UTC 2021
by
admin
on
Sat Jun 26 03:44:21 UTC 2021
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Record UNII |
60KQZ0388Y
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Record Status |
Validated (UNII)
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Record Version |
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FDA ORPHAN DRUG |
202005
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NCI_THESAURUS |
C1557
Created by
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EU-Orphan Drug |
EU/3/05/311
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7886
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C074908
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454194
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60KQZ0388Y
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TROXACITABINE
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3635
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145918-75-8
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C1438
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145918-75-8
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DB04961
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M11238
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PRIMARY | Merck Index | ||
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SUB22612
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CHEMBL359164
Created by
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |