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Allopurinol

Allopurinol Structure
CAS No.
315-30-0
Chemical Name:
Allopurinol
Synonyms
HPP;ALO;1H-PYRAZOLO[3,4-D]PYRIMIDIN-4-OL;Zyloprim;1H-pyrazolo[4,3-d]pyriMidin-7-ol;Allopurinol CRS;4-HPP;Pural;Remid;Urbol
CBNumber:
CB1181254
Molecular Formula:
C5H4N4O
Molecular Weight:
136.11
MOL File:
315-30-0.mol
MSDS File:
SDS
Modify Date:
2024/5/14 9:30:11
Request For Quotation

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. 15-25°C
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
BCS Class 3,1
InChIKey OFCNXPDARWKPPY-UHFFFAOYSA-N
CAS DataBase Reference 315-30-0(CAS DataBase Reference)
NIST Chemistry Reference Allopurinol(315-30-0)
EPA Substance Registry System Allopurinol (315-30-0)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H301-H317
Precautionary statements  P280-P301+P310+P330-P302+P352
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
Toxicity LD50 oral in mouse: 78mg/kg
NFPA 704
1
3 0

Allopurinol price More Price(8)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) A8003 Allopurinol xanthine oxidase inhibitor 315-30-0 5G ₹3388.23 2022-06-14 Buy
Sigma-Aldrich(India) PHR1377 Allopurinol Pharmaceutical Secondary Standard; Certified Reference Material 315-30-0 1G ₹7609.98 2022-06-14 Buy
Sigma-Aldrich(India) A8003 Allopurinol xanthine oxidase inhibitor 315-30-0 25G ₹10868.3 2022-06-14 Buy
ALFA India ALF-A16974-14 4-Hydroxy-1H-pyrazolo[3,4-d]pyrimidine, 98% 315-30-0 25g ₹5904 2022-05-26 Buy
ALFA India ALF-A16974-06 4-Hydroxy-1H-pyrazolo[3,4-d]pyrimidine, 98% 315-30-0 5g ₹2660 2022-05-26 Buy
Product number Packaging Price Buy
A8003 5G ₹3388.23 Buy
PHR1377 1G ₹7609.98 Buy
A8003 25G ₹10868.3 Buy
ALF-A16974-14 25g ₹5904 Buy
ALF-A16974-06 5g ₹2660 Buy

Allopurinol Chemical Properties,Uses,Production

Chemical Properties

White to Off-White Solid

Uses

Allopurinol does not reduce serum uric acid levels by increasing renal uric acid excretion; instead it lowers plasma urate levels by inhibiting the final steps in uric acid biosynthesis.
Uric acid in humans is formed primarily by xanthine oxidase-catalyzed oxidation of hypoxanthine and xanthine to uric acid. Allopurinol (8) and its primary metabolite, alloxanthine (9) [CAS: 2465-59-0], are inhibitors of xanthine oxidase. Inhibition of the last two steps in uric acid biosynthesis by blocking xanthine oxidase reduces the plasma concentration and urinary excretion of uric acid and increases the plasma levels and renal excretion of the more soluble oxypurine precursors. Normally, in humans the urinary purine content is almost solely uric acid; treatment with allopurinol results in the urinary excretion of hypoxanthine, xanthine, and uric acid, each with its independent solubility. Lowering the uric acid concentration in plasma below its limit of solubility facilitates the dissolution of uric acid deposits. The effectiveness of allopurinol in the treatment of gout and hyperuricemia that results from hematogical disorders and antineoplastic therapy has been demonstrated.

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.

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.

Pharmacokinetics

Allopurinol was synthesized in 1956 as part of a study of purine antagonists. It is well absorbed on oral administration, with peak plasma concentrations appearing within 1 hour. Decreases of uric acid can be observed within 24 to 48 hours. Excretion of allopurinol and its metabolite occurs primarily in the urine, with approximately 20% of a dose being excreted in the feces.

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.

Metabolism

Allopurinol is rapidly metabolized via oxidation and the formation of numerous ribonucleoside derivatives. The major oxidation metabolite, alloxanthine or oxypurinol, has a much longer half-life (18–30 hours versus 2–3 hours) than the parent drug and is an effective, although less potent, inhibitor of xanthine oxidase. The longer plasma half-life of alloxanthine results in an accumulation in the body during chronic administration, thus contributing significantly to the overall therapeutic effects of allopurinol.

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

Hydrazinium hydroxide solution Ethyl 3-amino-4-pyrazolecarboxylate 2-Cyanoacetamide Ethyl (ethoxymethylene)cyanoacetate Ethyl cyanoacetate
Morpholine Hydrazine hydrate Triethyl orthoformate
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Preparation Products

1H-Pyrazolo[3,4-d]pyrimidin-4-amine, N-methyl- (9CI)

Allopurinol Suppliers

Global( 844)Suppliers
Supplier Tel Country ProdList Advantage Inquiry
Jigs Chemical ltd +919099003427 Gujarat, India 239 58 Inquiry
Acura Life Sciences +917780672646 Hyderabad, India 37 58 Inquiry
GOALSY PHARMA +91-8247562464 +91-9885583385 Hyderabad, India 479 58 Inquiry
BIOCHEMICAL & SYNTHETIC PRODUCTS PVT. LT., +91-91-8421973722 +91-9869455944 Telangana, India 31 58 Inquiry
Anant Pharmaceuticals Pvt Ltd +91-8550986868 +91-9485998001 Haryana, India 461 58 Inquiry
J S LABS +91-7330612784 +91-7330612784 Tamil Nadu, India 160 58 Inquiry
SNECOFRi Pvt Ltd +91-9032850129 +91-9032850129 Telangana, India 404 58 Inquiry
AARTIA KEM SCIENCE +91-8291072530 +91-8291072530 Maharashtra, India 70 58 Inquiry
Gonane Pharma +91-9819380043 +91-9819380043 NaviMumbai, India 192 58 Inquiry
Cefa-Cilinas Biotics Pvt Ltd +91-7875033155 +91-8080701561 Maharashtra, India 121 58 Inquiry
Supplier Advantage
Jigs Chemical ltd 58
Acura Life Sciences 58
GOALSY PHARMA 58
BIOCHEMICAL & SYNTHETIC PRODUCTS PVT. LT., 58
Anant Pharmaceuticals Pvt Ltd 58
J S LABS 58
SNECOFRi Pvt Ltd 58
AARTIA KEM SCIENCE 58
Gonane Pharma 58
Cefa-Cilinas Biotics Pvt Ltd 58

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Allopurinol Spectrum

Allopurinol(315-30-0)MSAllopurinol(315-30-0)1HNMRAllopurinol(315-30-0)IR1Allopurinol(315-30-0)IR2Allopurinol(315-30-0)Raman

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