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
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)
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| 5-Ethynyluracil (776C85): protection from 5-fluorouracil-induced neurotoxicity in dogs. | 1994 Jul 19 |
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| Oral fluoropyrimidines: are they the equivalent of parenteral infusional 5-fluorouracil? | 2001 |
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| Phase II study of oral eniluracil, 5-fluorouracil, and leucovorin in patients with advanced colorectal carcinoma. | 2001 Apr 1 |
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| New options for outpatient chemotherapy--the role of oral fluoropyrimidines. | 2001 Aug |
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| Crystal structure prediction for eniluracil. | 2001 Aug |
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| Oral eniluracil/5-FU for advanced colon and breast carcinomas. | 2001 Jan |
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| 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 |
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| Peripheral neuropathy associated with weekly oral 5-fluorouracil, leucovorin and eniluracil. | 2001 Jul |
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| A phase II trial of oral eniluracil/5-fluorouracil in patients with inoperable hepatocellular carcinoma. | 2001 Jul |
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| Extraction of 5-fluorouracil by tumor and liver: a noninvasive positron emission tomography study of patients with gastrointestinal cancer. | 2001 Jul 1 |
|
| Advances in the treatment of metastatic colorectal cancer. | 2001 May |
|
| A phase II study of oral eniluracil/fluorouracil in patients with anthracycline-refractory or anthracycline- and taxane-refractory advanced breast cancer. | 2001 Sep |
|
| A phase I trial of weekly paclitaxel plus prolonged oral eniluracil/5-fluorouracil in patients with refractory malignancies. | 2002 |
|
| Oral eniluracil/5-fluorouracil in patients with inoperable hepatocellular carcinoma. | 2002 Apr |
|
| Role of body surface area in dosing of investigational anticancer agents in adults, 1991-2001. | 2002 Dec 18 |
|
| 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 |
|
| An evolving role for oral fluoropyrimidine drugs. | 2002 Feb 15 |
|
| Comparative pharmacokinetic study of continuous venous infusion fluorouracil and oral fluorouracil with eniluracil in patients with advanced solid tumors. | 2002 Mar 15 |
|
| 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 |
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| Can eniluracil improve 5-fluorouracil therapy? | 2002 May |
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| Inhibiting 5-fluorouracil breakdown: a broken down approach to 5-fluorouracil modulation. | 2002 May |
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| Estimation of the effect of food on the disposition of oral 5-fluorouracil in combination with eniluracil. | 2002 May |
|
| 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 |
|
| 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 |
|
| Pharmacokinetic and pharmacodynamic effects of oral eniluracil, fluorouracil and leucovorin given on a weekly schedule. | 2003 Jul |
|
| 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 |
|
| Dihydropyrimidine dehydrogenase (DPD) rapidly regenerates after inactivation by eniluracil (GW776C85) in primary and metastatic colorectal cancer. | 2003 Nov |
|
| Augmentation of the antitumor activity of capecitabine by a tumor selective dihydropyrimidine dehydrogenase inhibitor, RO0094889. | 2003 Sep 20 |
|
| Treatment of colorectal cancer metastasis: the role of chemotherapy. | 2004 Jan-Jun |
|
| 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 |
|
| 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 |
|
| The multidisciplinary management of gastrointestinal cancer. The integration of cytotoxics and biologicals in the treatment of metastatic colorectal cancer. | 2007 |
|
| 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 |
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FDA ORPHAN DRUG |
211505
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NCI_THESAURUS |
C1557
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NCI_THESAURUS |
C2019
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C073482
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m4908
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C1773
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100000078921
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II-19
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59989-18-3
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ACTIVE MOIETY
