Allopurinol

Base Information

• Chemical Name: Allopurinol
• CAS No.: 315-30-0
• Molecular Formula: C5H4N4O
• Molecular Weight: 136.113
• Hs Code.: 29335990
• Mol file: 315-30-0.mol

Synonyms:4H-Pyrazolo(3,4-d)pyrimidin-4-one;Hexanuret;Apulonga;1H-Pyrazolo(3,4-d)pyrimidin-4-ol;Zyloric;4-Hydroxy-1H-pyrazolo[3,4-d]pyrimidine;Lopurin;Monarch;Takanarumin;Dabrosin;Uricemil;Suspendol;2,4,8,9-tetrazabicyclo[4.3.0]nona-1,3,6-trien-5-one;BW 56-158;Urbol;1,5-Dihydro-4H-pyrazolo(3,4-d)pyrimidine-4-one;Alositol;Allozym;Foligan;Milurit;Apurin;Alopurinol [INN-Spanish];Allopurinolum [INN-Latin];Allopurinol (JP14/USP);1, 5-Dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one;4-Hydroxypyrazolyl(3,4-d)pyrimidine;Dura Al;Zyloprim (TN);Urtias 100;Ailural;4H-Pyrazolo[3, 4-d]pyrimidin-4-one, 1,5-dihydro-;Urolit;4-Hydroxypyrazolyl[3, 4-d]pyrimidine;4H-Pyrazolo[3,4-d]pyrimidin-4-one,1,5- dihydro-;Epuric;1H-Pyrazolo[3, 4-d]pyrimidin-4-ol;Gotax;4-Hydroxypyrazolo[3,4-d]pyrimidine;Anoprolin;4-Hydroxy-1H-pyrazolo(3,4-d)pyrimidine;Aluline;Cellidrin;HPP;4-Hydroxypyrazolol(3,4-d)pyrimidine;Allo-Puren;4-Hydroxypyrazolopyrimidine;Nektrohan;Geapur;

Chemical Property of Allopurinol

Chemical Property:

• Appearance/Colour: white to off-white solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Refractive Index: 1.816
• Boiling Point: 423.27 °C at 760 mmHg
• PKA: 10.2(at 25℃)
• Flash Point: 209.787 °C
• PSA: 74.43000
• Density: 1.702 g/cm³
• LogP: -0.35380
• Storage Temp.: Room temperature.
• Solubility.: 1 M NaOH: soluble50mg/mL, clear to very slightly hazy, colorless
• Water Solubility.: 0.35 g/L (25 ºC)

Purity/Quality:

98%-102%, ^*data from raw suppliers

Allopurinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,T, Xn
• Hazard Codes: T,Xi,Xn
• Statements: 25-43-36/37/38-20/21/22
• Safety Statements: 28-36/37-45-36/37/39-26-24-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Clinical Uses: Allopurinol is utilized to prevent or reduce high uric acid levels in the blood, which can lead to conditions like gout or gouty arthritis. It is also employed to manage excess uric acid levels caused by cancer medications or in patients with kidney stones. Allopurinol functions by replacing purine in the body's purine metabolism pathway, thereby reducing the synthesis and accumulation of uric acid.
• Mechanism of Action: Allopurinol is an isomer of hypoxanthine and functions as an inhibitor of xanthine oxidase (XO). It competitively inhibits xanthine oxidase, reducing the generation of oxygen free radicals during reperfusion. By inhibiting xanthine oxidase, allopurinol prevents the conversion of hypoxanthine and xanthine into uric acid, thereby reducing uric acid levels in the blood and urine.
• Production Methods: Allopurinol can be prepared using various methods, including the hydrogenation method, cation reaction method, and pyrimidine-S-oxidase method. The hydrogenation method is the most common approach for synthesizing allopurinol. A new production process involves condensation, cyclization salt reaction, crude product section, and refining section, resulting in high-quality allopurinol with increased yield.

Technology Process of Allopurinol

There total 16 articles about Allopurinol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

formic acid (64-18-6) + 2-cyano-3-morpholinoacrylamide (25229-97-4) + formamide (77287-34-4,77287-35-5,60100-09-6) → 4-hydroxypyrazolo(3,4-d)pyrimidine (315-30-0)

Guidance literature:

2-cyano-3-morpholinoacrylamide; With hydrazine hydrate; In water; at 90 - 100 ℃;

formic acid; formamide; at 100 - 170 ℃;

Reference yield: 89.0%

5-amino-1H-pyrazole-4-carboxamide hemisulfate + sodium formate (141-53-7) → Allopurinol (315-30-0)

Guidance literature:

at 190 ℃; for 4h; Neat (no solvent); Inert atmosphere;

DOI:10.1002/hlca.200890102

Reference yield: 88.0%

ethyl 5-amino-1H-pyrazole-4-carboxylate (1260243-04-6,6994-25-8) + trimethyl orthoformate (149-73-5) → Allopurinol (315-30-0)

Guidance literature:

With ammonium acetate; In methanol; at 130 ℃; for 8h;

upstream raw materials:

3-amino-4-pyrazolecarboxylic acid ethyl ester

formamide

3-amino-4-pyrazolocarboxamide hemisulfate

2-Methoxycarbonylhydrazonomethyl-3-chlor-5-dimethylamino-4-aza-2,4-pentadiennitril

Downstream raw materials:

2,5-dihydro-2,5-dimethyl-4H-pyrazolo<3,4-d>pyrimidin-4-one

1,5-dimethylallopurinol

4-Mercapto-1H-pyrazolo<3,4-d>pyrimidine

4-chloro-1H-pyrazolo[3,4-d]pyrimidine

Refernces

• 1、 -. "Synthetic method of allopurinol". Paragraph 0005; 0028-0029; 0032-0033; 0036-0037; 0040-0041. . Retrieved 2018/03/01.
• 2、 Ho, Jonathan Z.,Van Arsdale, Kyle R.,Braun, Matthew P.. "Efficient synthesis of14C-labeled 1H-pyrazolo[3,4-d]pyrimidine and related [4.3.0]-bicyclic pyrimidino systems". scheme or table. p. 958 - 963. Retrieved 2009/03/11.