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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

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q12882|||Q16761
Gene ID: 1806.0
Gene Symbol: DPYD
Target Organism: Homo sapiens (Human)
1.6 µM [Ki]
PubMed

PubMed

TitleDatePubMed
5-Ethynyluracil (776C85): protection from 5-fluorouracil-induced neurotoxicity in dogs.
1994 Jul 19
Oral eniluracil/5-FU for advanced colon and breast carcinomas.
2001 Jan
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
Peripheral neuropathy associated with weekly oral 5-fluorouracil, leucovorin and eniluracil.
2001 Jul
A phase II study of oral eniluracil/fluorouracil in patients with anthracycline-refractory or anthracycline- and taxane-refractory advanced breast cancer.
2001 Sep
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
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
Pharmacokinetic and pharmacodynamic effects of oral eniluracil, fluorouracil and leucovorin given on a weekly schedule.
2003 Jul
A dose-escalating study of oral eniluracil/5-fluorouracil plus oxaliplatin in patients with advanced gastrointestinal malignancies.
2003 Jun
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
A semi-automated non-radioactive system for measuring recovery of RNA synthesis and unscheduled DNA synthesis using ethynyluracil derivatives.
2010 May 4
Patents

Sample Use Guides

Phase II study: 20 mg twice daily for a month.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:12:37 UTC 2023
Edited
by admin
on Wed Jul 05 23:12:37 UTC 2023
Record UNII
2E2W0W5XIU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
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
Created by admin on Wed Jul 05 23:12:37 UTC 2023 , Edited by admin on Wed Jul 05 23:12:37 UTC 2023
NCI_THESAURUS C1557
Created by admin on Wed Jul 05 23:12:37 UTC 2023 , Edited by admin on Wed Jul 05 23:12:37 UTC 2023
NCI_THESAURUS C2019
Created by admin on Wed Jul 05 23:12:37 UTC 2023 , Edited by admin on Wed Jul 05 23:12:37 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID10208696
Created by admin on Wed Jul 05 23:12:37 UTC 2023 , Edited by admin on Wed Jul 05 23:12:37 UTC 2023
PRIMARY
PUBCHEM
43157
Created by admin on Wed Jul 05 23:12:37 UTC 2023 , Edited by admin on Wed Jul 05 23:12:37 UTC 2023
PRIMARY
INN
7624
Created by admin on Wed Jul 05 23:12:37 UTC 2023 , Edited by admin on Wed Jul 05 23:12:37 UTC 2023
PRIMARY
EVMPD
SUB13674MIG
Created by admin on Wed Jul 05 23:12:37 UTC 2023 , Edited by admin on Wed Jul 05 23:12:37 UTC 2023
PRIMARY
FDA UNII
2E2W0W5XIU
Created by admin on Wed Jul 05 23:12:37 UTC 2023 , Edited by admin on Wed Jul 05 23:12:37 UTC 2023
PRIMARY
MESH
C073482
Created by admin on Wed Jul 05 23:12:37 UTC 2023 , Edited by admin on Wed Jul 05 23:12:37 UTC 2023
PRIMARY
MERCK INDEX
M4908
Created by admin on Wed Jul 05 23:12:37 UTC 2023 , Edited by admin on Wed Jul 05 23:12:37 UTC 2023
PRIMARY Merck Index
NCI_THESAURUS
C1773
Created by admin on Wed Jul 05 23:12:37 UTC 2023 , Edited by admin on Wed Jul 05 23:12:37 UTC 2023
PRIMARY
SMS_ID
100000078921
Created by admin on Wed Jul 05 23:12:37 UTC 2023 , Edited by admin on Wed Jul 05 23:12:37 UTC 2023
PRIMARY
DRUG BANK
DB03516
Created by admin on Wed Jul 05 23:12:37 UTC 2023 , Edited by admin on Wed Jul 05 23:12:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL355200
Created by admin on Wed Jul 05 23:12:37 UTC 2023 , Edited by admin on Wed Jul 05 23:12:37 UTC 2023
PRIMARY
USAN
II-19
Created by admin on Wed Jul 05 23:12:37 UTC 2023 , Edited by admin on Wed Jul 05 23:12:37 UTC 2023
PRIMARY
CAS
59989-18-3
Created by admin on Wed Jul 05 23:12:37 UTC 2023 , Edited by admin on Wed Jul 05 23:12:37 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY