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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 of TROXACITABINE

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.

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
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 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
  • Download
Name Type Language
TROXACITABINE
INN   MI   USAN   WHO-DD  
USAN   INN  
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
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
NCI_THESAURUS C1557
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
EU-Orphan Drug EU/3/05/311
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
Code System Code Type Description
INN
7886
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
PRIMARY
MESH
C074908
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
PRIMARY
PUBCHEM
454194
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
PRIMARY
USAN
KK-68
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
PRIMARY
FDA UNII
60KQZ0388Y
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
PRIMARY
WIKIPEDIA
TROXACITABINE
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
PRIMARY
DRUG CENTRAL
3635
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID2048791
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
PRIMARY
NCI_THESAURUS
C1438
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
PRIMARY
CAS
145918-75-8
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
PRIMARY
DRUG BANK
DB04961
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
PRIMARY
MERCK INDEX
m11238
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
PRIMARY Merck Index
SMS_ID
100000088103
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
PRIMARY
EVMPD
SUB22612
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
PRIMARY
ChEMBL
CHEMBL359164
Created by admin on Fri Dec 15 15:59:20 UTC 2023 , Edited by admin on Fri Dec 15 15:59:20 UTC 2023
PRIMARY
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CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY