110690-43-2

Basic information

• Product Name: EMITEFUR
• Synonyms: EMITEFUR;3-[[3-(Ethoxymethyl)-5-fluoro-3，6-dihydro-2，6-dioxo-1(2H)-pyrim-idinyl]carbonyl]benzoic acid 6-(benzoyloxy)- 3-cyano-2-pyridinyl ester;3-[[[3-(Ethoxymethyl)-5-fluoro-1,2,3,6-tetrahydro-2,6-dioxopyrimidin]-1-yl]carbonyl]benzoic acid 6-(benzoyloxy)-3-cyano-2-pyridinyl ester;3-[[3-(Ethoxymethyl)-5-fluoro-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-1-yl]carbonyl]benzoic acid 6-(benzoyloxy)-3-cyano-2-pyridyl ester;BOF-A2;BOF-A-2
• CAS NO: 110690-43-2
• Molecular Formula: C28H19FN4O8
• Molecular Weight: 558.47
• Mol File: 110690-43-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 162-164°
• Boiling Point: 755.1 °C at 760 mmHg
• Flash Point: 410.5 °C
• Appearance: /
• Density: 1.52 g/cm³
• Vapor Pressure: 1.09E-22mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: 2-8°C
• PKA: -5.94±0.40(Predicted)
• CAS DataBase Reference: EMITEFUR(CAS DataBase Reference)
• NIST Chemistry Reference: EMITEFUR(110690-43-2)
• EPA Substance Registry System: EMITEFUR(110690-43-2)

Safety Data

• Hazardous Substances Data: 110690-43-2(Hazardous Substances Data)

Usage

Uses

EMITEFUR is used for antineoplastic, it is used in the treatment of stomach, colorectal, breast, nonsmall cell lung, and pancreatic cancers (inhibits DNA synthesis and RNA function).

Hazard

A poison by ingestion. A reproductive hazard.

Safety Profile

A poison by ingestion andsubcutaneous routes. Experimental reproductive effects.Mutation data reported. When heated to decomposition itemits toxic vapors of NOx and F-.

InChI:InChI=1/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

Upstream product

• 35441-10-2 3-cyano-2,6-dihydroxypyridine 
• 98-88-4 benzoyl chloride 
• 57610-22-7 1-ethoxymethyl-5-fluorouracil 
• 103941-70-4 6-benzoyloxy-3-cyano-2-pyridone 
• 99-63-8 benzene-1,3-dicarbonyl dichloride 
• 65-85-0 benzoic acid 

Relevant articles and documents

Synthesis of 5-fluorouracil derivatives containing an inhibitor of 5- fluorouracil degradation

The reactivities of 5-fluorouracil (5-FUra) degradation inhibitors, 2,4- (2) and 2,6-dihydroxypyridines (3), were investigated. Acylation of 2 and 2,4-bis(trimethylsilyloxy)pyridines with equimolar amounts of acid chlorides preferentially occurred at the 4-OH and 2-OH positions, respectively, and the structure of monobenzoylated 5-chloro-2,4-dihydroxypyridine (2b) was determined as 4-benzoyloxy-5-chloro-2-pyridone (5b) by X-ray crystallographic analysis. Compounds 2 and 3, as well as the N-2-tetrahydrofuryl (11), N- alkyl (12), and N-carbamoyl (14) derivatives of 2, exhibit dynamic keto-enol tautomerism. The acyl derivatives of these pyridines are labile and are thought to be active esters. Monoacyl ester derivatives of these pyridines were combined with 5-FUra analogs to develop novel antitumor agents containing an inhibitor of 5-FUra degradation. One of them, 3-[3-(6- benzoyloxy-3-cyano-2-pyridyloxycarbonyl)benzoyl]-1-ethoxymethyl-5- fluorouracil (BOF-A2) (22b), was the most effective and is currently undergoing late phase-II clinical trials.

5-fluorouracil derivatives

An anticancer compound is disclosed which is represented by the formula STR1 wherein one of R1 and R2 is a phenyl-lower alkyl optionally having a substituent, phenyl-lower alkenyl or naphthyl-lower alkyl, the other of R1 and R2 is hydrogen or acyl, and R3 is hydrogen, acyl or tetrahydrofuranyl, or represented by the formula STR2 wherein Rx is an optionally substituted pyridyl, Y is arylene and α is a known 5-fluorouracil derivative residue which can be converted to 5-fluorouracil in vivo and which is linked to the carbonyl by an ester or amide linkage.