ENOCITABINE

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 Search

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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/3858569
Curator's Comment: http://www.ncbi.nlm.nih.gov/pubmed/3861233

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 Target	Pharmacology	Condition	Potency
cell growth 21 Target ID: GO:0016049 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3861233	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute myeloid leukemia 136 Sources: http://www.ncbi.nlm.nih.gov/pubmed/3858569	Primary		Approved 8429	SUNRABIN Approved Use Unknown

PubMed

Title	Date	PubMed
[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 Mar	16447716
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 Nov	17916082
The clinical outcome of FLAG chemotherapy without idarubicin in patients with relapsed or refractory acute myeloid leukemia.	2009 Jun	19543516
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 Jan	20052341

Patents

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.

Name

Type

Language

ENOCITABINE

Official Name

English

Enocitabine [WHO-DD]

Common Name

English

N-(1-.BETA.-D-ARABINOFURANOSYL-1,2-DIHYDRO-2-OXO-4-PYRIMIDINYL)DOCOSANAMIDE

Common Name

English

ENOCITABINE [JAN]

Common Name

English

SUNRABIN

Brand Name

English

enocitabine [INN]

Common Name

English

NSC-239336

Code

English

ENOCITABINE [MI]

Common Name

English

ENOCITABINE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1557