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

Molecular Formula	C6H4N2O2
Molecular Weight	136.1082
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/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
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
Role of body surface area in dosing of investigational anticancer agents in adults, 1991-2001.	2002 Dec 18	12488482
An evolving role for oral fluoropyrimidine drugs.	2002 Feb 15	11844808
Comparative pharmacokinetic study of continuous venous infusion fluorouracil and oral fluorouracil with eniluracil in patients with advanced solid tumors.	2002 Mar 15	11896120
Phase II trial of 5-fluorouracil plus eniluracil in patients with advanced pancreatic cancer: a Southwest Oncology Group study.	2002 Oct	12377645
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
A dose-escalating study of oral eniluracil/5-fluorouracil plus oxaliplatin in patients with advanced gastrointestinal malignancies.	2003 Jun	12796023
Augmentation of the antitumor activity of capecitabine by a tumor selective dihydropyrimidine dehydrogenase inhibitor, RO0094889.	2003 Sep 20	12866042
A Phase I trial of preoperative eniluracil plus 5-fluorouracil and radiation for locally advanced or unresectable adenocarcinoma of the rectum and colon.	2004 Mar 1	14967434
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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:43:48 GMT 2023` Edited by `admin` on `Fri Dec 15 15:43:48 GMT 2023`
Record UNII	2E2W0W5XIU
Record Status	`Validated (UNII)`
Record Version

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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