ENILURACIL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H4N2O2
Molecular Weight	136.1082
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1NC=C(C#C)C(=O)N1

InChI

InChIKey=JOZGNYDSEBIJDH-UHFFFAOYSA-N

InChI=1S/C6H4N2O2/c1-2-4-3-7-6(10)8-5(4)9/h1,3H,(H2,7,8,9,10)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1544906 | https://www.ncbi.nlm.nih.gov/pubmed/11081572 | https://www.ncbi.nlm.nih.gov/pubmed/11060767

Eniluracil (5-ethynyluracil, GW 776, 776C85) is a potent irreversible inhibitor of dihydropyrimidine dehydrogenase, the first enzyme in the catabolic pathway of 5-fluorouracil (5-FU), the most widely used drug in cancer chemotherapy. Eniluracil increases the oral bioavailability of 5-FU to 100%, facilitating uniform absorption and predictable toxicity. Eniluracil was being developed as a novel modulator of 5-FU for the treatment of cancer.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dihydropyrimidine dehydrogenase [NADP(+)] 4 Target ID: Q12882\|\|\|Q16761 Gene ID: 1806.0 Gene Symbol: DPYD Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11060767	Inhibitor 8297		1.6 µM [Ki]

PubMed

Title	Date	PubMed
A National Cancer Institute of Canada clinical trials group phase II study of eniluracil (776C85) and oral 5-fluorouracil in patients with advanced squamous cell head and neck cancer.	2001 Jul	11521795
Extraction of 5-fluorouracil by tumor and liver: a noninvasive positron emission tomography study of patients with gastrointestinal cancer.	2001 Jul 1	11431319
A phase I trial of weekly paclitaxel plus prolonged oral eniluracil/5-fluorouracil in patients with refractory malignancies.	2002	12401907
Oral eniluracil/5-fluorouracil in patients with inoperable hepatocellular carcinoma.	2002 Apr	12056708
Comparative pharmacokinetic study of continuous venous infusion fluorouracil and oral fluorouracil with eniluracil in patients with advanced solid tumors.	2002 Mar 15	11896120
Randomized, open-label, phase III study of a 28-day oral regimen of eniluracil plus fluorouracil versus intravenous fluorouracil plus leucovorin as first-line therapy in patients with metastatic/advanced colorectal cancer.	2002 Mar 15	11896100
Pharmacokinetic and pharmacodynamic effects of oral eniluracil, fluorouracil and leucovorin given on a weekly schedule.	2003 Jul	12707718
Dihydropyrimidine dehydrogenase (DPD) rapidly regenerates after inactivation by eniluracil (GW776C85) in primary and metastatic colorectal cancer.	2003 Nov	12904894
A phase I study of eniluracil/5-FU in combination with radiation therapy for potentially resectable and/or unresectable cancer of the pancreas and distal biliary tract.	2006 Feb	16466986
A possible cause and remedy for the clinical failure of 5-fluorouracil plus eniluracil.	2010 Jan	20100689

Patents

Sample Use Guides

In Vivo Use Guide

Phase II study: 20 mg twice daily for a month.

Route of Administration: Oral

Name

Type

Language

ENILURACIL

Official Name

English

ETHYNYLURACIL

Systematic Name

English

776C85

Code

English

eniluracil [INN]

Common Name

English

ENILURACIL [MART.]

Common Name

English

ENILURACIL [MI]

Common Name

English

776-C-85

Code

English

5-ETHYNYL-URACIL

Systematic Name

English

ENILURACIL [USAN]

Common Name

English

5-Ethynyluracil

Systematic Name

English

Eniluracil [WHO-DD]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

211505