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
5-Ethynyluracil (776C85): protection from 5-fluorouracil-induced neurotoxicity in dogs.	1994 Jul 19	8053919
Oral fluoropyrimidines: are they the equivalent of parenteral infusional 5-fluorouracil?	2001	11768039
New options for outpatient chemotherapy--the role of oral fluoropyrimidines.	2001 Aug	11545541
Peripheral neuropathy associated with weekly oral 5-fluorouracil, leucovorin and eniluracil.	2001 Jul	11459999
A phase II study of oral eniluracil/fluorouracil in patients with anthracycline-refractory or anthracycline- and taxane-refractory advanced breast cancer.	2001 Sep	11697836
Role of body surface area in dosing of investigational anticancer agents in adults, 1991-2001.	2002 Dec 18	12488482
Multicenter phase II study of a 28-day regimen of orally administered eniluracil and fluorouracil in the treatment of patients with anthracycline- and taxane-resistant advanced breast cancer.	2002 Feb 15	11844821
An evolving role for oral fluoropyrimidine drugs.	2002 Feb 15	11844808
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
Can eniluracil improve 5-fluorouracil therapy?	2002 May	12453337
Phase I study of eniluracil and oral 5-fluorouracil in combination with docetaxel in the treatment of patients with metastatic breast carcinoma.	2002 May 1	12015755
Eniluracil's need for a targeted approach: a lesson in drug development.	2002 Sep 1	12202681
A study to evaluate the pharmacokinetics of oral 5-fluorouracil and eniluracil after concurrent administration to patients with refractory solid tumours and varying degrees of renal impairment (FUMA1005).	2003 Jan	12497207
Pharmacokinetic and pharmacodynamic effects of oral eniluracil, fluorouracil and leucovorin given on a weekly schedule.	2003 Jul	12707718
Practical considerations in the use of oral fluoropyrimidines.	2003 Jun	12802799
A dose-escalating study of oral eniluracil/5-fluorouracil plus oxaliplatin in patients with advanced gastrointestinal malignancies.	2003 Jun	12796023
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

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