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

Details

Stereochemistry ABSOLUTE
Molecular Formula C31H55N3O6
Molecular Weight 565.7849
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ENOCITABINE

SMILES

CCCCCCCCCCCCCCCCCCCCCC(=O)NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O

InChI

InChIKey=SAMRUMKYXPVKPA-VFKOLLTISA-N
InChI=1S/C31H55N3O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-27(36)32-26-22-23-34(31(39)33-26)30-29(38)28(37)25(24-35)40-30/h22-23,25,28-30,35,37-38H,2-21,24H2,1H3,(H,32,33,36,39)/t25-,28-,29+,30-/m1/s1

HIDE SMILES / InChI

Description

Enocitabine is an anti-cancer nucleoside that was developed for the treatment of acute myeloid leukemia. Although the exact mechanism of its action is unknow, Enocitabine effectively inhibits tumor cell growht in vitro and the inhibition is supposed to be related to its metabolism to Ara-C, an inhibitor of DNA polymerase. The drug was approved in Japan and Korea and was marketed under the name Sunrabin, however, its current marketing status is unknown and is assumed to be discontinued.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SUNRABIN

Cmax

ValueDoseCo-administeredAnalytePopulation
0.26 μg/mL
700 mg/m² single, intravenous
CYTARABINE plasma
Homo sapiens
173.4 μg/mL
700 mg/m² single, intravenous
ENOCITABINE plasma
Homo sapiens
0.102 μg/mL
700 mg/m² single, intravenous
CYTARABINE plasma
Homo sapiens
3.5 μg/mL
700 mg/m² single, intravenous
SPONGOURIDINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
429.8 μg × h/mL
700 mg/m² single, intravenous
ENOCITABINE plasma
Homo sapiens
0.858 μg × h/mL
700 mg/m² single, intravenous
CYTARABINE plasma
Homo sapiens
62.62 μg × h/mL
700 mg/m² single, intravenous
SPONGOURIDINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
5.76 h
4 mg/kg single, intravenous
ENOCITABINE plasma
Homo sapiens
3.65 h
700 mg/m² single, intravenous
CYTARABINE plasma
Homo sapiens
4.28 h
700 mg/m² single, intravenous
ENOCITABINE plasma
Homo sapiens
11.2 h
700 mg/m² single, intravenous
CYTARABINE plasma
Homo sapiens
0.37 h
200 mg/m² single, intravenous
ENOCITABINE plasma
Homo sapiens
5.27 h
200 mg/m² single, intravenous
ENOCITABINE plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
170 mg/m2 per day,
Route of Administration: Intravenous
In Vitro Use Guide
T-cell depleted mononuclear cells from AML pa tients were exposed to Enocitabine at various doses (17.7, 35.3. or 70.7 uM) for 1, 6, or 24 h. Then the cell suspension was washed three times in alpha-MEM with 10% PCS, plated in methylcellulose culture, and incubated for another 7 days in the absence of the drug. Enocitabine suppressed primary and secondary blast colony formation in a dose responsive manner.