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59989-18-3,MFCD00871973
Catalog No.:AA00EEK6

59989-18-3 | 5-ethynyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

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10mg
≥98%
in stock  
$62.00   $43.00
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50mg
97%
in stock  
$100.00   $70.00
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200mg
>97.0%(T)(HPLC)
in stock  
$230.00   $161.00
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250mg
97%
in stock  
$231.00   $162.00
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1g
>97.0%(T)(HPLC)
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$796.00   $557.00
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00EEK6
Chemical Name:
5-ethynyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
CAS Number:
59989-18-3
Molecular Formula:
C6H4N2O2
Molecular Weight:
136.1082
MDL Number:
MFCD00871973
SMILES:
C#Cc1c[nH]c(=O)[nH]c1=O
NSC Number:
687296
Properties
Computed Properties
 
Complexity:
269  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
10  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
1  
XLogP3:
-0.7  

Literature

Title: Final results of a prematurely discontinued Phase 1/2 study of eniluracil with escalating doses of 5-fluorouracil administered orally in patients with advanced hepatocellular carcinoma.

Journal: Cancer chemotherapy and pharmacology 20111001

Title: Determination of eniluracil and 5-fluorouracil in human plasma by LC-MS/MS.

Journal: Bioanalysis 20101201

Title: A semi-automated non-radioactive system for measuring recovery of RNA synthesis and unscheduled DNA synthesis using ethynyluracil derivatives.

Journal: DNA repair 20100504

Title: A possible cause and remedy for the clinical failure of 5-fluorouracil plus eniluracil.

Journal: Clinical colorectal cancer 20100101

Title: The multidisciplinary management of gastrointestinal cancer. The integration of cytotoxics and biologicals in the treatment of metastatic colorectal cancer.

Journal: Best practice & research. Clinical gastroenterology 20070101

Title: 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.

Journal: Cancer investigation 20060201

Title: A Phase I trial of preoperative eniluracil plus 5-fluorouracil and radiation for locally advanced or unresectable adenocarcinoma of the rectum and colon.

Journal: International journal of radiation oncology, biology, physics 20040301

Title: Treatment of colorectal cancer metastasis: the role of chemotherapy.

Journal: Cancer metastasis reviews 20040101

Title: Dihydropyrimidine dehydrogenase (DPD) rapidly regenerates after inactivation by eniluracil (GW776C85) in primary and metastatic colorectal cancer.

Journal: Cancer chemotherapy and pharmacology 20031101

Title: Augmentation of the antitumor activity of capecitabine by a tumor selective dihydropyrimidine dehydrogenase inhibitor, RO0094889.

Journal: International journal of cancer 20030920

Title: Pharmacokinetic and pharmacodynamic effects of oral eniluracil, fluorouracil and leucovorin given on a weekly schedule.

Journal: Cancer chemotherapy and pharmacology 20030701

Title: A dose-escalating study of oral eniluracil/5-fluorouracil plus oxaliplatin in patients with advanced gastrointestinal malignancies.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20030601

Title: Practical considerations in the use of oral fluoropyrimidines.

Journal: Seminars in oncology 20030601

Title: Design and synthesis of the tumor-activated prodrug of dihydropyrimidine dehydrogenase (DPD) inhibitor, RO0094889 for combination therapy with capecitabine.

Journal: Bioorganic & medicinal chemistry letters 20030310

Title: Heterotopic ossification in rectal cancer: Rare finding with a novel proposed mechanism.

Journal: Journal of surgical oncology 20030201

Title: 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).

Journal: Cancer chemotherapy and pharmacology 20030101

Title: Role of body surface area in dosing of investigational anticancer agents in adults, 1991-2001.

Journal: Journal of the National Cancer Institute 20021218

Title: Phase I study of eniluracil, oral 5-fluororacil and gemcitabine in patients with advanced malignancy.

Journal: Investigational new drugs 20021101

Title: 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.

Journal: Investigational new drugs 20021101

Title: Phase II trial of 5-fluorouracil plus eniluracil in patients with advanced pancreatic cancer: a Southwest Oncology Group study.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20021001

Title: Eniluracil's need for a targeted approach: a lesson in drug development.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20020901

Title: Estimation of the effect of food on the disposition of oral 5-fluorouracil in combination with eniluracil.

Journal: Cancer chemotherapy and pharmacology 20020501

Title: Impact of two weekly schedules of oral eniluracil given with fluorouracil and leucovorin on the duration of dihydropyrimidine dehydrogenase inhibition.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20020501

Title: Phase I study of eniluracil and oral 5-fluorouracil in combination with docetaxel in the treatment of patients with metastatic breast carcinoma.

Journal: Cancer 20020501

Title: Eastern Cooperative Oncology Group phase II trial (E4296) of oral 5-fluorouracil and eniluracil as a 28-day regimen in metastatic colorectal cancer.

Journal: Clinical colorectal cancer 20020501

Title: Inhibiting 5-fluorouracil breakdown: a broken down approach to 5-fluorouracil modulation.

Journal: Clinical colorectal cancer 20020501

Title: Can eniluracil improve 5-fluorouracil therapy?

Journal: Clinical colorectal cancer 20020501

Title: Oral eniluracil/5-fluorouracil in patients with inoperable hepatocellular carcinoma.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20020401

Title: 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.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20020315

Title: Comparative pharmacokinetic study of continuous venous infusion fluorouracil and oral fluorouracil with eniluracil in patients with advanced solid tumors.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20020315

Title: An evolving role for oral fluoropyrimidine drugs.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20020215

Title: 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.

Journal: Journal of clinical oncology : official journal of the American Society of Clinical Oncology 20020215

Title: A phase I trial of weekly paclitaxel plus prolonged oral eniluracil/5-fluorouracil in patients with refractory malignancies.

Journal: The oncologist 20020101

Title: New drugs and combinations in the palliative treatment of colon and rectal cancer.

Journal: European journal of surgical oncology : the journal of the European Society of Surgical Oncology and the British Association of Surgical Oncology 20010901

Title: A phase II study of oral eniluracil/fluorouracil in patients with anthracycline-refractory or anthracycline- and taxane-refractory advanced breast cancer.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20010901

Title: Crystal structure prediction for eniluracil.

Journal: Journal of pharmaceutical sciences 20010801

Title: New options for outpatient chemotherapy--the role of oral fluoropyrimidines.

Journal: Cancer treatment reviews 20010801

Title: Extraction of 5-fluorouracil by tumor and liver: a noninvasive positron emission tomography study of patients with gastrointestinal cancer.

Journal: Cancer research 20010701

Title: A phase II trial of oral eniluracil/5-fluorouracil in patients with inoperable hepatocellular carcinoma.

Journal: European journal of cancer (Oxford, England : 1990) 20010701

Title: Peripheral neuropathy associated with weekly oral 5-fluorouracil, leucovorin and eniluracil.

Journal: Anti-cancer drugs 20010701

Title: 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.

Journal: Annals of oncology : official journal of the European Society for Medical Oncology 20010701

Title: Advances in the treatment of metastatic colorectal cancer.

Journal: Clinical colorectal cancer 20010501

Title: Phase II study of oral eniluracil, 5-fluorouracil, and leucovorin in patients with advanced colorectal carcinoma.

Journal: Cancer 20010401

Title: Oral eniluracil/5-FU for advanced colon and breast carcinomas.

Journal: Oncology (Williston Park, N.Y.) 20010101

Title: Oral fluoropyrimidines: are they the equivalent of parenteral infusional 5-fluorouracil?

Journal: Cancer investigation 20010101

Title: The use of thymidylate synthase inhibitors in the treatment of advanced colorectal cancer: current status.

Journal: The oncologist 19990101

Title: 5-Ethynyluracil (776C85): protection from 5-fluorouracil-induced neurotoxicity in dogs.

Journal: Biochemical pharmacology 19940719

Title: Schilsky RL, et al. Eniluracil: an irreversible inhibitor of dihydropyrimidine dehydrogenase. Expert Opin Investig Drugs. 2000 Jul;9(7):1635-49.

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