 Home > Encyclopedia > Emitefur

Emitefur

Emitefur structure

CAS No:
110690-43-2
Formula:
C28H19FN4O8
Chemical Name:
Emitefur
Synonyms:
Benzoic acid,3-[[3-(ethoxymethyl)-5-fluoro-3,6-dihydro-2,6-dioxo-1(2H)-pyrimidinyl]carbonyl]-,6-(benzoyloxy)-3-cyano-2-pyridinyl ester;BOF-A 2;Emitefur
Categories:
Active Pharmaceutical Ingredients > Antineoplastic Agents

Description

Emitefur is an orally available antimetabolite composed of the 1-ethoxymethyl derivative of 5-fluorouracil (5-FU) and the dihydropyrimidine dehydrogenase (DPYD) inhibitor 3-cyano-2,6-dihydroxypyridine (CNDP) in a 1:1 molar ratio, with antineoplastic activity. Upon administration, the prodrug emitefur is converted into 5-FU, while CNDP prevents the degradation of 5-FU by inhibiting DPYD and thereby prolonging the half-life of 5-FU. This increases 5-FU's concentration and thus its antitumor activity through inhibition of DNA and RNA synthesis, as well as inhibition of thymidylate synthase activity. In addition, by inhibiting the formation of 5-FU metabolites, some toxic effects associated with these metabolites may be reduced. DPYD is the rate-limiting enzyme in the catabolism of 5-FU.

Emitefur Basic Attributes

Molecular Weight：

558.47

Exact Mass：

558.47

UNII：

9I50NF4AQ2

DSSTox ID：

DTXSID80149360

NCI Thesaurus Code：

C1022

Characteristics

PSA：

156

XLogP3：

2.53668

Density：

1.52±0.1 g/cm3(Predicted)

Melting Point：

162-164 °C

Boiling Point：

755.1±70.0 °C(Predicted)

Flash Point：

410.5ºC

Refractive Index：

1.663

Vapor Pressure：

1.09E-22mmHg at 25°C

Toxicity：

LD50 in mice, male rats, female rats (mg/kg): >5000, 1850, 1934 orally (Kiroshita)

Drug Information

MeSH：

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

MeSH Entry Terms：

3 (3-(6-benzoyloxy-3-cyano-2-pyridyloxycarbonyl)benzoyl)-1-ethoxymethyl-5-fluorouracil

Emitefur Use and Manufacturing

Methods of Manufacturing

Isophthaloyl chloride (I) and compound (II) are refluxed in dioxane under the action of triethylamine to obtain compound (III) by condensation. The compound (IV) is then refluxed in triethylamine and acetonitrile to obtain pyrizofluoride. The compound (IV) used in the above synthesis can be obtained by condensing benzoyl chloride and 3-cyano-2, 6-dihydroxypyridine in triethylamine and dimethylformamide.

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).

Computed Properties

Molecular Weight:558.5
XLogP3:3.6
Hydrogen Bond Acceptor Count:11
Rotatable Bond Count:10
Exact Mass:558.11869174
Monoisotopic Mass:558.11869174
Topological Polar Surface Area:156
Heavy Atom Count:41
Complexity:1110
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Dimethylformamide