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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 of ENILURACIL

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

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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Dihydropyrimidine dehydrogenase [NADP(+)]
4
Target ID: Q12882|||Q16761
Gene ID: 1806.0
Gene Symbol: DPYD
Target Organism: Homo sapiens (Human)
Inhibitor
8504
 1.6 µM [Ki]
PubMed

PubMed

TitleDatePubMed
Advances in the treatment of metastatic colorectal cancer.
2001 May
A phase I trial of weekly paclitaxel plus prolonged oral eniluracil/5-fluorouracil in patients with refractory malignancies.
2002
An evolving role for oral fluoropyrimidine drugs.
2002 Feb 15
Can eniluracil improve 5-fluorouracil therapy?
2002 May
Inhibiting 5-fluorouracil breakdown: a broken down approach to 5-fluorouracil modulation.
2002 May
Biochemical modulation of 5-fluorouacil through dihydropyrimidine dehydrogenase inhibition: a Southwest Oncology Group phase II trial of eniluracil and 5-fluorouracil in advanced resistant colorectal cancer.
2002 Nov
Phase I study of eniluracil, oral 5-fluororacil and gemcitabine in patients with advanced malignancy.
2002 Nov
Phase II trial of 5-fluorouracil plus eniluracil in patients with advanced pancreatic cancer: a Southwest Oncology Group study.
2002 Oct
Eniluracil's need for a targeted approach: a lesson in drug development.
2002 Sep 1
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
Practical considerations in the use of oral fluoropyrimidines.
2003 Jun
A dose-escalating study of oral eniluracil/5-fluorouracil plus oxaliplatin in patients with advanced gastrointestinal malignancies.
2003 Jun
Augmentation of the antitumor activity of capecitabine by a tumor selective dihydropyrimidine dehydrogenase inhibitor, RO0094889.
2003 Sep 20
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
Determination of eniluracil and 5-fluorouracil in human plasma by LC-MS/MS.
2010 Dec
A possible cause and remedy for the clinical failure of 5-fluorouracil plus eniluracil.
2010 Jan
Patents

Patents

05817664
2
07704971
2

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 Mon Mar 31 18:06:56 GMT 2025
Edited
by admin
on Mon Mar 31 18:06:56 GMT 2025
Record UNII
2E2W0W5XIU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
776-C-85
Preferred Name English
ENILURACIL
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
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
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
Created by admin on Mon Mar 31 18:06:56 GMT 2025 , Edited by admin on Mon Mar 31 18:06:56 GMT 2025
NCI_THESAURUS C1557
Created by admin on Mon Mar 31 18:06:56 GMT 2025 , Edited by admin on Mon Mar 31 18:06:56 GMT 2025
NCI_THESAURUS C2019
Created by admin on Mon Mar 31 18:06:56 GMT 2025 , Edited by admin on Mon Mar 31 18:06:56 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID10208696
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PRIMARY
PUBCHEM
43157
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PRIMARY
INN
7624
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PRIMARY
EVMPD
SUB13674MIG
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PRIMARY
FDA UNII
2E2W0W5XIU
Created by admin on Mon Mar 31 18:06:56 GMT 2025 , Edited by admin on Mon Mar 31 18:06:56 GMT 2025
PRIMARY
MESH
C073482
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PRIMARY
MERCK INDEX
m4908
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PRIMARY Merck Index
NCI_THESAURUS
C1773
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PRIMARY
SMS_ID
100000078921
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PRIMARY
DRUG BANK
DB03516
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PRIMARY
ChEMBL
CHEMBL355200
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PRIMARY
USAN
II-19
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PRIMARY
CAS
59989-18-3
Created by admin on Mon Mar 31 18:06:56 GMT 2025 , Edited by admin on Mon Mar 31 18:06:56 GMT 2025
PRIMARY
Related Record Type Details
Structure of ENILURACIL
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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