EMITEFUR

Details

Stereochemistry	ACHIRAL
Molecular Formula	C28H19FN4O8
Molecular Weight	558.4709
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOCN1C=C(F)C(=O)N(C(=O)C2=CC(=CC=C2)C(=O)OC3=C(C=CC(OC(=O)C4=CC=CC=C4)=N3)C#N)C1=O

InChI

InChIKey=WTSKMKRYHATLLL-UHFFFAOYSA-N

InChI=1S/C28H19FN4O8/c1-2-39-16-32-15-21(29)25(35)33(28(32)38)24(34)18-9-6-10-19(13-18)27(37)41-23-20(14-30)11-12-22(31-23)40-26(36)17-7-4-3-5-8-17/h3-13,15H,2,16H2,1H3

HIDE SMILES / InChI

Molecular Formula	C28H19FN4O8
Molecular Weight	558.4709
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8422172 | https://www.ncbi.nlm.nih.gov/pubmed/11219980 | https://adisinsight.springer.com/drugs/800002454

Emitefur or BOF-A2 is a fluorinated pyrimidine antimetabolite exerting antineoplastic properties. It is a compound composed of 5-fluorouracil (5-FU) and 3-cyano-2,6-dihydroxypyridine (CNDP), an inhibitor of 5-FU degradation by dihydrouracil dehydrogenase in order to prolong the blood 5-FU level as well as increase selective toxicity to a tumor. Emitefur demonstrated clinical activity in preliminary studies in Japan. Emitefur development for the treatment of solid tumors has been discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
[Development of fluorinated pyrimidines in Japan].	1993 Jan	8422172
Efficacy of a new 5-fluorouracil derivative, BOF-A2, in advanced non-small cell lung cancer. A multi-center phase II study.	1994	7917366

Sample Use Guides

In Vivo Use Guide

a multi-center phase II study: the patients were scheduled to receive at least 2 courses of treatment, each consisting of 200 mg twice daily for 2 weeks followed by a 2-week rest period.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:24:59 GMT 2023` Edited by `admin` on `Sat Dec 16 17:24:59 GMT 2023`
Record UNII	9I50NF4AQ2
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

EMITEFUR

Official Name

English

EMITEFUR [USAN]

Common Name

English

M-((3-(ETHOXYMETHYL)-5-FLUORO-3,6-DIHYDRO-2,6-DIOXO-1(2H)-PYRIMIDINYL)CARBONYL)BENZOIC ACID, 2-ESTER WITH 2,6-DIHYDROXYNICOTINONITRILE BENZOATE (ESTER)

Common Name

English

EMITEFUR [MI]

Common Name

English

3-((3-(ETHOXYMETHYL)-5-FLUORO-3,6-DIHYDRO-2,6-DIOXO-1(2H)-PYRIMIDINYL)CARBONYL)BENZOIC ACID, 6-(BENZOYLOXY)-3-CYANO-2-PYRIDINYL ESTER

Common Name

English

EMITEFUR [JAN]

Common Name

English

BOF-A2

Code

English

emitefur [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1557