2207-75-2

Basic information

• Product Name: Potassium oxonate
• Synonyms: 1,4,5,6-tetrahydro-4,6-dioxo-s-triazine-2-carboxylicacid,potassiumsalt;5-azaoroticacid,potassiumsalt;kox;potassiumazaorotate;POTASSIUM OXONATE;POTASSIUM 4,6-DIHYDROXY-1,3,5-TRIAZINE-2-CARBOXYLATE;Potassium 1,4,5,6-tetrahydro-4,6-dioxo-1,3,5-triazine-2-carboxylate;POTASSIUM ALLANTOXANATE
• CAS NO: 2207-75-2
• Molecular Formula: C₄H₂N₃O₄*K
• Molecular Weight: 195.17
• EINECS: 218-627-5
• Product Categories: Classes of Metal Compounds;K (Potassium) Compounds (excluding simple potassium salts);Typical Metal Compounds;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;oncology;Anti-cancer&immunity;Anticancer
• Mol File: 2207-75-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 300 °C(lit.)
• Appearance: White/Powder
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: Aqueous Base (Slightly), Water (Slightly, Heated, Sonicated)
• Water Solubility: Soluble in hot water.
• CAS DataBase Reference: Potassium oxonate(CAS DataBase Reference)
• NIST Chemistry Reference: Potassium oxonate(2207-75-2)
• EPA Substance Registry System: Potassium oxonate(2207-75-2)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: RR4580000
• Hazardous Substances Data: 2207-75-2(Hazardous Substances Data)

Usage

Description

Potassium oxonate, also known as oxonic acid potassium salt, is a uricase inhibitor that prevents the metabolism and excretion of uric acid. It is an off-white solid and is a component of S-1, a mixture containing a prodrug of the antitumor agent 5-fluorouracil (5-FU). Potassium oxonate is used in various applications due to its ability to suppress gastrointestinal toxicity without inhibiting antitumor activity.

Uses

1. Used in Anticancer Applications:
Potassium oxonate is used as an antitumor effect potentiator and antitumor agent for its ability to suppress the gastrointestinal toxicity of 5-FU without inhibiting its antitumor activity in rats. This makes it a valuable component in the treatment of various cancers.
2. Used in Gastrointestinal Toxicity Management:
Potassium oxonate is used as an inhibitor of 5-fluorouracil-induced gastrointestinal toxicity in rats, allowing for the maintenance of the antitumor activity of 5-FU while reducing its side effects.
3. Used in Hyperuricemia Induction:
Potassium oxonate is used to induce hyperuricemia in rats by inhibiting uric acid metabolism, which can be useful in studying the effects of hyperuricemia on the body and the development of potential treatments.
4. Used in the Treatment of Specific Cancers:
Formulations containing potassium oxonate have been used to treat gastric, pancreatic, lung, head, neck, and breast carcinomas, thanks to its role in the S-1 mixture and its ability to reduce gastrointestinal toxicity while maintaining antitumor efficacy.

InChI:InChI=1/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

Synthetic route

oxaluric acid (585-05-7) + urea (57-13-6) → monopotassium 1,2,3,4-tetrahydro-2,4-dioxo-1,3,5-triazine-6-carboxylate (2207-75-2)

Conditions	Yield
Stage #1: oxaluric acid; urea With toluene-4-sulfonic acid In ethanol at 50℃; for 6h; Stage #2: With potassium hydroxide In ethanol; water at 0℃; for 2h; pH=5.5; Temperature; Reagent/catalyst; Solvent; pH-value;	94.64%

Allantoin (97-59-6) → monopotassium 1,2,3,4-tetrahydro-2,4-dioxo-1,3,5-triazine-6-carboxylate (2207-75-2)

Conditions	Yield
With N-Bromosuccinimide; potassium iodide; potassium hydroxide In water at 0 - 25℃; for 3h; Temperature; Reagent/catalyst; Darkness;	91.32%

dehydro-allantoin (105245-87-2) → monopotassium 1,2,3,4-tetrahydro-2,4-dioxo-1,3,5-triazine-6-carboxylate (2207-75-2)

Conditions	Yield
With potassium hydroxide In water for 0.333333h;	82%

acetic acid (64-19-7) + Allantoin (97-59-6) → monopotassium 1,2,3,4-tetrahydro-2,4-dioxo-1,3,5-triazine-6-carboxylate (2207-75-2)

Conditions	Yield
Stage #1: Allantoin With bromine; potassium iodide; potassium hydroxide In water at 0 - 25℃; for 30h; Stage #2: acetic acid In water at 0 - 5℃; pH=5; Time;	76.1%

water (7732-18-5) + monopotassium 1,2,3,4-tetrahydro-2,4-dioxo-1,3,5-triazine-6-carboxylate (2207-75-2) + cobalt(II) perchlorate hexahydrate → [(cobalt(II))3(oxonate)3(H2O)6]2*13H2O

Conditions	Yield
In methanol	80%

iron(II) perchlorate monohydrate + water (7732-18-5) + monopotassium 1,2,3,4-tetrahydro-2,4-dioxo-1,3,5-triazine-6-carboxylate (2207-75-2) → [(iron(II))3(oxonate)3(H2O)6]2*13H2O

Conditions	Yield
In methanol	78%

Upstream product

• 105245-87-2 dehydro-allantoin 
• 64-19-7 acetic acid 
• 97-59-6 Allantoin 
• 585-05-7 oxaluric acid 
• 57-13-6 urea 

Relevant articles and documents

Preparation method of oteracil potassium

The invention provides a preparation method of oteracil potassium. The method comprises the following steps: dissolving allantoin, an alkali and potassium iodide in purified water at room temperature;and cooling an obtained reaction solution, adding N-halogenated amide in batches, carrying out heating reaction after the addition is completed, cooling the reaction solution after the reaction is detected to be completed, adjusting the pH value with an acid, carrying out suction filtration after stirring and crystal growing, washing a filter cake with cold purified water until the filter cake iscolorless, leaching with a cold anhydrous alcohol solvent, and carrying out vacuum drying to obtain potassium oteracil. Compared with the prior art, the method has the advantages of simple and easilyavailable raw materials, simple operation, mild reaction conditions, stable quality, high yield, no pollution to the environment, and suitableness for industrial production.

Method for preparing potassium oxonate

The invention belongs to the technical field of chemical synthesis and particularly relates to a method for preparing potassium oxonate, comprising the following steps: dissolving potassium hydroxide in water, clarifying and then cooling to 0-5 DEG C, adding potassium iodide, adding allantoin in batch, stirring for dissolving, dropwise adding bromine at a controlled temperature of 0-5 DEG C for 7-11 h, stirring at 0-5 DEG C for 1 after dropwise adding, heating to 20-25 DEG C and reacting for 18-22 h, and detecting allantoin being 0.6% through HPLC (high performance liquid chromatography), cooling to 0-5 DEG C, dropwise adding acetic acid to adjust pH to 5, filtering, washing with water, washing with ethanol, and drying to obtain the potassium oxonate. The method has good reaction effect, high product yield and low cost, is simple to perform and is particularly applicable to industrial application.

THE MECHANISM FOR THE CONVERSION OF URIC ACID INTO ALLANTOIN AND DEHYDRO-ALLANTOIN. A NEW LOOK AT AN OLD PROBLEM

The reaction of uric acids 1 with iodine in alkaline solution yields, on acidification, new dehydroallantoins 11, or normal oxidation products, allantoins 13, depending on whether an excess or a stoichiometric amount of oxidant was used.The structure and regiochemistry of dehydro-allantoins 11 was established by chemical, spectroscopic, and 14C-labelling methods.These experimental results, in combination with other data, generate a new mechanistic scheme for the uricolytic pathway to allantoin, ruling out the intervention of a symmetrical transition state prior to the decarboxylation step.