(+/-)-Sulfinpyrazone

Toxicity

Symptoms of overdose include nausea, vomiting, diarrhea, epigastric pain, ataxia, labored respiration, convulsions, coma. Possible symptoms, seen after overdosage with other pyrazolone derivatives: anemia, jaundice, and ulceration.

Description

Sulfinpyrazone is soluble in alkaline solutions. Its synthesis is similar to that of phenylbutazone (Fig. 36.33). It produces its uricosuric effect in a manner similar to that of probenecid. A dose of 35 mg produces a uricosuric effect equivalent to that produced by 100 mg of probenecid, whereas 400 mg/day of sulfinpyrazone produces an effect comparable to that obtained with doses of 1.5 to 2 g of probenecid. It also possesses, not surprisingly, some of the properties of phenylbutazone. It is an inhibitor of human platelet prostaglandin synthesis at the cyclooxygenase step, resulting in a decrease in platelet release and a reduction in platelet aggregation. This antiplatelet effect suggests a role for sulfinpyrazone in reducing the incidence of sudden death, which can occur in the first year following a myocardial infarction; however, it lacks the analgetic and anti-inflammatory effects of phenylbutazone.

The Uses of (+/-)-Sulfinpyrazone

As an anti-inflammatory and uricosuric agent, its side effects were severe enough to preclude its continuous use in the treatment of chronic gout. Evaluation of several chemical congeners indicated that the phenylthioethyl analog of phenylbutazone had promising anti-inflammatory and uricosuric activity. A metabolite, the sulfoxide pyrazone, exhibited enhanced uricosuric activity. Interestingly, the corresponding sulfone does not appear to be a metabolite. Sulfinpyrazone lacks the clinically striking anti-inflammatory and analgesic properties of phenylbutazone.

Background

A uricosuric drug that is used to reduce the serum urate levels in gout therapy. It lacks anti-inflammatory, analgesic, and diuretic properties.

Indications

For the treatment of gout and gouty arthritis.

What are the applications of Application

(±)-Sulfinpyrazone is a free radical scavenger that inhibits organic anion transporters

Pharmacokinetics

Sulfinpyrazone's pharmacologic activity is the potentiation of the urinary excretion of uric acid. It is useful for reducing the blood urate levels in patients with chronic tophaceous gout and acute intermittent gout, and for promoting the resorption of tophi.

Metabolism