Oteracil potassiumProduct ingredient for Oteracil

Name
Oteracil potassium
Drug Entry
Oteracil

Oteracil is an adjunct to antineoplastic therapy, used to reduce the toxic side effects associated with chemotherapy. Approved by the European Medicines Agency (EMA) in March 2011, Oteracil is available in combination with Gimeracil and Tegafur within the commercially available product "Teysuno". The main active ingredient in Teysuno is Tegafur, a pro-drug of Fluorouracil (5-FU), which is a cytotoxic anti-metabolite drug that acts on rapidly dividing cancer cells. By mimicking a class of compounds called "pyrimidines" that are essential components of RNA and DNA, 5-FU is able to insert itself into strands of DNA and RNA, thereby halting the replication process necessary for continued cancer growth.

Oteracil's main role within Teysuno is to reduce the activity of 5-FU within normal gastrointestinal mucosa, and therefore reduce's gastrointestinal toxicity 1. It functions by blocking the enzyme orotate phosphoribosyltransferase (OPRT), which is involved in the production of 5-FU.

Accession Number
DBSALT001274
Structure
Synonyms
Not Available
UNII
4R7FFA00RX
CAS Number
2207-75-2
Weight
Average: 195.175
Monoisotopic: 194.96823705
Chemical Formula
C4H2KN3O4
InChI Key
IAPCTXZQXAVYNG-UHFFFAOYSA-M
InChI
InChI=1S/C4H3N3O4.K/c8-2(9)1-5-3(10)7-4(11)6-1;/h(H,8,9)(H2,5,6,7,10,11);/q;+1/p-1
IUPAC Name
potassium 6-hydroxy-4-oxo-4,5-dihydro-1,3,5-triazine-2-carboxylate
SMILES
[K+].OC1=NC(=NC(=O)N1)C([O-])=O
KEGG Compound
C15997
ChemSpider
66073
ChEBI
80230
ChEMBL
CHEMBL3184847
Predicted Properties
PropertyValueSource
Water Solubility7.35 mg/mLALOGPS
logP-0.55ALOGPS
logP-0.75ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)-8.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area114.18 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity41.06 m3·mol-1ChemAxon
Polarizability11.58 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon