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Allopurinol

Allopurinol
Allopurinol structure
CAS No.
315-30-0
Chemical Name:
Allopurinol
Synonyms
HPP;ALO;4-HPP;Remid;Urbol;Pural;AL-100;aloral;Anzief;Apurin
CBNumber:
CB1181254
Molecular Formula:
C5H4N4O
Formula Weight:
136.11
MOL File:
315-30-0.mol

Allopurinol Properties

Melting point:
>300 °C(lit.)
Boiling point:
250.36°C (rough estimate)
Density 
1.4295 (rough estimate)
refractive index 
1.8500 (estimate)
storage temp. 
Room temperature.
solubility 
1 M NaOH: soluble50mg/mL, clear to very slightly hazy, colorless to faintly yellow
form 
Powder
pka
10.2(at 25℃)
color 
White or almost white
Water Solubility 
0.35 g/L (25 ºC)
Merck 
14,279
InChIKey
OFCNXPDARWKPPY-UHFFFAOYSA-N
CAS DataBase Reference
315-30-0(CAS DataBase Reference)
NIST Chemistry Reference
Allopurinol(315-30-0)
EPA Substance Registry System
4H-Pyrazolo[3,4- d]pyrimidin-4-one, 1,5-dihydro-(315-30-0)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  T,Xi,Xn
Risk Statements  25-43-36/37/38-20/21/22
Safety Statements  28-36/37-45-36/37/39-26-24-36
RIDADR  UN 2811 6.1/PG 3
WGK Germany  2
RTECS  UR0785000
TSCA  Yes
HazardClass  6.1
PackingGroup  III
HS Code  29335990
Hazardous Substances Data 315-30-0(Hazardous Substances Data)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H301 Toxic if swalloed Acute toxicity,oral Category 3 Danger P264, P270, P301+P310, P321, P330,P405, P501
H317 May cause an allergic skin reaction Sensitisation, Skin Category 1 Warning P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
Precautionary statements:
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P270 Do not eat, drink or smoke when using this product.
P272 Contaminated work clothing should not be allowed out of the workplace.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P321 Specific treatment (see … on this label).
P301+P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P405 Store locked up.
P501 Dispose of contents/container to..…

Allopurinol price More Price(12)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich A8003 Allopurinol xanthine oxidase inhibitor 315-30-0 5g $57.2 2018-11-13 Buy
Sigma-Aldrich 1013002 Allopurinol United States Pharmacopeia (USP) Reference Standard 315-30-0 250mg $348 2018-11-13 Buy
TCI Chemical A0907 Allopurinol >98.0%(T) 315-30-0 25g $30 2018-11-22 Buy
TCI Chemical A0907 Allopurinol >98.0%(T) 315-30-0 250g $150 2018-11-22 Buy
Alfa Aesar A16974 4-Hydroxy-1H-pyrazolo[3,4-d]pyrimidine, 98% 315-30-0 25g $105 2018-11-13 Buy

Allopurinol Chemical Properties,Uses,Production

Chemical Properties

White to Off-White Solid

Uses

antihyperuricemia, antigout, antiurolithic

Uses

Xanthine oxidase inhibitor; decreases uric acid production. Used in treatment of hyperuricemia and chronic gout. Antiurolithic

Indications

Allopurinol (Zyloprim) is the drug of choice in the treatment of chronic tophaceous gout and is especially useful in patients whose treatment is complicated by renal insufficiency.

brand name

Lopurin (Abbott); Lopurin (BASF); Zyloprim (Promethus).

General Description

Odorless tasteless white microcrystalline powder.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Allopurinol is an aminoalcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Allopurinol darkens above 572° F, and at an indefinite high temperature, Allopurinol chars and decomposes. At 221° F, maximum stability occurs at pH 3.1- 3.4. Allopurinol decomposes in acidic and basic solutions.

Fire Hazard

Flash point data for Allopurinol are not available; however, Allopurinol is probably combustible.

Mechanism of action

Allopurinol, in contrast to the uricosuric drugs, reduces serum urate levels through a competitive inhibition of uric acid synthesis rather than by impairing renal urate reabsorption. This action is accomplished by inhibiting xanthine oxidase, the enzyme involved in the metabolism of hypoxanthine and xanthine to uric acid. After enzyme inhibition, the urinary and blood concentrations of uric acid are greatly reduced and there is a simultaneous increase in the excretion of the more soluble uric acid precursors, xanthine and hypoxanthine.
Allopurinol itself is metabolized by xanthine oxidase to form the active metabolite oxypurinol, which tends to accumulate after chronic administration of the parent drug.This phenomenon contributes to the therapeutic effectiveness of allopurinol in long-term use. Oxypurinol is probably responsible for the antigout effects of allopurinol. Oxypurinol itself is not administered because it is not well absorbed orally.

Clinical Use

Allopurinol is especially indicated in the treatment of chronic tophaceous gout, since patients receiving it show a pronounced decrease in their serum and urinary uric acid levels. Because it does not depend on renal mechanisms for its efficacy, allopurinol is particularly beneficial for patients who already have developed renal uric acid stones, patients with excessively high urate excretion (e.g., above 1,200 mg in 24 hours), patients with a variety of blood disorders (e.g., leukemia, polycythemia vera), patients with excessive tophus deposition, and patients who fail to respond well to the uricosuric drugs.
Allopurinol also inhibits reperfusion injury. This injury occurs when organs that either have been transplanted or have had their usual blood perfusion blocked are reperfused with blood or an appropriate buffer solution. The cause of this injury is local formation of free radicals, such as the superoxide anion, the hydroxyl free radical, or peroxynitrite. These substances are strong oxidants and are quite damaging to tissues.

Side effects

Common toxicities associated with allopurinol administration include a variety of skin rashes, gastrointestinal upset, hepatotoxicity, and fever. These reactions are often sufficiently severe to dictate termination of drug therapy. It is advised that therapy not be initiated during an acute attack of gouty arthritis. As with the uricosuric drugs, therapy with allopurinol should be accompanied both by a sufficient increase in fluid intake to ensure water diuresis and by alkalinization of the urine. Prophylactic use of colchicine also helps to prevent acute attacks of gout that may be brought on during the initial period of allopurinol ingestion.

Safety Profile

Human poison by ingestion. Poison experimentally by intraperitoneal and subcutaneous routes. An experimental teratogen. Human systemic effects by ingestion: blood leukopenia, dermatitis, jaundice, muscle weakness, thrombocytopenia. When heated to decomposition it emits toxic fumes of NOx. An FDA proprietary drug used as a xanthine oxidase inhibitor.

Enzyme inhibitor

This purine analogue (FW = 136.11 g/mol; CAS 315-30-0), also known by the trade names Zyloprim? and Lopurin? and by its systematic name 4- hydroxypyrazolo (3,4-d) pyrimidine, is used mainly to treat gout by inhibiting xanthine oxidase, thereby limiting the build-up of uric acid. Allopurinol and oxipurinol are metabolically converted by purine nucleoside phosphorylase to their corresponding L-ribosyl derivatives that are then phosphorylated. History: Seeking to retard the breakdown of the anticancer drug mercaptopurine, which is used to treat acute lymphoblastic leukemia, Nobelist Gertrude Elion and coworkers synthesized allopurinol to enhance mercaptopurine’s action. Allopurinol is a slowly catalyzed alternative substrate for xanthine oxidase, which produces oxipurinol (See Oxipurinol). Because oxipurinol dissociates extremely slow (t1/2 = 300 min) from the enzyme, oxipurinol is a potent xanthine oxidase product inhibitor. Therapeutic Use: Allopurinol is dispensed as 30-mg and 100-mg tablets. Its long-term use is generally unremarkable, but both allopurinol and oxipurinol cause orotic aciduria (from < 2 mg/day to 6-30 mg/day) and orotidinuria (from < 3 mg/day to 24-55 mg/day), while also increasing orotidine:PRPP transferase and orotidylate decarboxylase activity, for which they are inhibitors. Allopurinol Hypersensitivity: Allopurinol-derived oxypurinol is a common cause of severe cutaneous adverse drug reactions (SCAR), including Stevens-Johnson Syndrome (SJS) and Toxic Epidermal Necrolysis (TEN). A strong association between “allopurinol”-induced SCAR and the Human Leukocyte Antigen HLA-B*5801 was observed in a Han Chinese population, with high frequency of this allele, whereas there is only a moderate association was observed in European and Japanese populations, where this allele has a low frequency. Although genotyping is now required to identify individuals susceptible to SJS prior to starting abacavir and carbamazepine therapy (See Abacavir and Carbamazepine), no such screening is advocated for allopurinol, in part due to the lack of rapid/inexpensive screening for the HLA-B*58:01 allele. Pharmacokinetics: After oral dosage, the PK parameters of allopurinol include an oral bioavailability of 79%, an elimination t of 1.2 hours, an apparent oral 1/2 clearance of 15.8 mL/min/kg, and an apparent volume of distribution of 1.31 L/kg. Assuming that 90 mg of oxipurinol is formed from every 100mg of allopurinol, the pharmacokinetic parameters of oxipurinol in subjects with normal renal function are a t1/2 of 23 hours, CL/F of 0.31 mL/min/kg, Vd/F of 0.59 L/kg, and renal clearance (relative to creatinine) of 0.19. Oxipurinol is cleared almost entirely by urinary excretion. Key Pharmacokinetic Parameters: See Appendix II in Goodman & Gilman’s THE PHARMACOLOGICAL BASIS OF THERAPEUTICS, 12th Edition (Brunton, Chabner & Knollmann, eds.) McGraw-Hill Medical, New York. Target (s) : xanthine oxidase, slow, tight-binding inhibitor ; orotate phosphoribosyl-transferase; purine nucleoside phosphorylase; tryptophan pyrrolase, or tryptophan 2,3-dioxygenase ; salicylhydroxamic acid reductase; guanine deaminase; glutamine:D-fructose-6-phosphate aminotransferase; xanthine phosphoribosyl-transferase; hypoxanthine (guanine) phosphoribosyl-transferase; xanthine dehydrogenase ; orotidine:PRPP transferase and orotidylate decarboxylase.

Precautions

Since allopurinol is metabolized by the hepatic microsomaldrug-metabolizing enzymes, coadministration ofdrugs also metabolized by this system should be donewith caution. Because allopurinol inhibits the oxidationof mercaptopurine and azathioprine, their individualadministered doses must be decreased by as much as75% when they are given together with allopurinol.Allopurinol may also increase the toxicity of other cytotoxicdrugs (e.g., vidarabine). The actions of allopurinolare not antagonized by the coadministration of salicylates.

Allopurinol Preparation Products And Raw materials

Raw materials

Preparation Products


Allopurinol Suppliers

Global( 383)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Capot Chemical Co.,Ltd.
+86 (0)571-855 867 18
+86 (0)571-858 647 95 sales@capotchem.com China 19919 60
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 21930 58
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20680 55
Shanghai Time Chemicals CO., Ltd.
+86-021-57951555
+86-021-57951555 jack.li@time-chemicals.com CHINA 1367 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32457 55
ATK CHEMICAL COMPANY LIMITED
+86 21 5161 9050/ 5187 7795
+86 21 5161 9052/ 5187 7796 ivan@atkchemical.com CHINA 24196 60
Anhui Royal Chemical Co., Ltd.
+86-025-86736275
dana.jiang@royal-chem.com CHINA 488 55
Xiamen AmoyChem Co., Ltd
+86 (0)592-605 1114
sales@amoychem.com CHINA 6374 58
Hebei Minshang Biotechnology Co., Ltd
+86-13230167943
cathy@hbminshang.com CHINA 279 58
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 20516 58

View Lastest Price from Allopurinol manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2019-04-02 Allopurinol Manufacturer; In stock GMP Factory
315-30-0
US $1.00 / KG 1KG High quality manufacturer TOP 3 largest production factory in China Chemwill Asia Co.,Ltd.
2018-12-23 Allopurinol
315-30-0
US $8.00 / kg 1kg 99% 10tons career henan chemical co
2018-12-21 Allopurinol
315-30-0
US $8.00 / kg 1kg 99% 10MT career henan chemical co

Allopurinol Spectrum


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