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
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
| Molecular Formula | C31H55N3O6 |
| Molecular Weight | 565.7849 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.26 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3592717/ |
700 mg/m² single, intravenous dose: 700 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
CYTARABINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
173.4 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8132852/ |
700 mg/m² single, intravenous dose: 700 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
ENOCITABINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
0.102 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8132852/ |
700 mg/m² single, intravenous dose: 700 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
CYTARABINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
3.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8132852/ |
700 mg/m² single, intravenous dose: 700 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
SPONGOURIDINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
429.8 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8132852/ |
700 mg/m² single, intravenous dose: 700 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
ENOCITABINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
0.858 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8132852/ |
700 mg/m² single, intravenous dose: 700 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
CYTARABINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
62.62 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8132852/ |
700 mg/m² single, intravenous dose: 700 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
SPONGOURIDINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.76 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3702507/ |
4 mg/kg single, intravenous dose: 4 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
ENOCITABINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: FEMALE / MALE food status: UNKNOWN |
|
3.65 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3592717/ |
700 mg/m² single, intravenous dose: 700 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
CYTARABINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
4.28 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8132852/ |
700 mg/m² single, intravenous dose: 700 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
ENOCITABINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
11.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8132852/ |
700 mg/m² single, intravenous dose: 700 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
CYTARABINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
0.37 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6850647/ |
200 mg/m² single, intravenous dose: 200 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
ENOCITABINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
5.27 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6850647/ |
200 mg/m² single, intravenous dose: 200 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered: |
ENOCITABINE plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Idarubicin plus behenoyl cytarabine and 6-thioguanine compares favorably with idarubicin plus cytarabine-based regimen for children with previously untreated acute myeloid leukemia: 10-year retrospective, multicenter study in Korea. | 2010-01 |
|
| The clinical outcome of FLAG chemotherapy without idarubicin in patients with relapsed or refractory acute myeloid leukemia. | 2009-06 |
|
| Gemtuzumab ozogamicin in combination with attenuated doses of standard induction chemotherapy can successfully induce complete remission without increasing toxicity in patients with acute myeloid leukemia aged 55 or older. | 2007-11 |
|
| [Adams-Stokes attack due to complete atrioventricular block in a patient with acute promyelocytic leukemia during remission induction therapy using all-trans retinoic acid]. | 2005-03 |
|
| [Successful treatment after acute promyelocytic leukemia (APL) syndrome of relapsed API with arsenic trioxide]. | 2003-03 |
|
| Close correlation of 1-beta-D-arabinofuranosylcytosine 5'-triphosphate, an intracellular active metabolite, to the therapeutic efficacy of N(4)-behenoyl-1-beta-D-arabinofuranosylcytosine therapy for acute myelogenous leukemia. | 2001-09 |
|
| Monitoring of intracellular 1-beta-D-arabinofuranosylcytosine 5'-triphosphate in 1-beta-D-arabinofuranosylcytosine therapy at low and conventional doses. | 2001-05 |
|
| All-trans retinoic acid-induced multiple mononeuropathies. | 1999-04 |
|
| Behenoyl cytarabine-associated reversible encephalopathy in a patient with acute myelogenous leukemia. | 1999-02 |
Patents
Sample Use Guides
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:29:46 GMT 2025
by
admin
on
Mon Mar 31 18:29:46 GMT 2025
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| Record UNII |
9YVR68W306
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C1557
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9YVR68W306
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C015019
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C1082
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5121
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CHEMBL2106589
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ENOCITABINE
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71734
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55726-47-1
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239336
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SUB06537MIG
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m4910
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100000080233
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DTXSID6046682
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1012
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