(+/-)-Sulfinpyrazone

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.

Sulfinpyrazone Basic information

Product Name:	(+/-)-Sulfinpyrazone
Synonyms:	SALOR-INT L129682-1EA;(+)-SULFINPYRAZONE; (+/-)-SULFINPYRAZONE; SULFINPYRAZONE; sulfoxyphenyl pyrazolidine; 1,2-diphenyl-4-(2-(phenylsulfinyl)ethyl)-3,5-pyrazolidinedione; 1,2-DIPHENYL-4-(PHENYLSUFINYLETHYL)-3,5-PYRAZOLIDINEDIONE; 1,2-DIPHENYL-4-[PHENYLSULFINYLETHYL]-3,5-PYRAZOLIDINEDIONE
CAS:	57-96-5
MF:	C23H20N2O3S
MW:	404.48
EINECS:	200-357-4
Product Categories:	API; ANTURANE
Mol File:	57-96-5.mol

Anturan Chemical Structure

+-Sulfinpyrazone

Anturane Chemical Properties

Melting point	136-137°
Boiling point	590.8±42.0 °C(Predicted)
density	1.1890 (rough estimate)
refractive index	1.6360 (estimate)
solubility	Very slightly soluble in water, sparingly soluble in ethanol (96 per cent). It dissolves in dilute solutions of alkali hydroxides.
form	neat
pka	pKa 2.8(H2O t = RT I undefined) (Uncertain)
Water Solubility	2.601g/L(22 ºC)
CAS DataBase Reference	57-96-5(CAS DataBase Reference)
NIST Chemistry Reference	Sulfinpyrazone(57-96-5)

Sulfinpyrazone Usage And Synthesis

Chemical Properties	White or almost white powder.
Originator	Anturane,Geigy,US,1959
Uses	Sulfinpyrazone is used upon exactly the same indications as phenylbutazone.
Uses	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.

Therapeutic Function

Antiarthritic (uricosuric)

Clinical Use

Sulfinpyrazone is a structural derivative of the anti-inflammatory drug phenylbutazone. Unlike phenylbutazone, however, sulfinpyrazone does not have significant anti-inflammatory activity. It does have potent uricosuric effects and frequently is used in the treatment of gout.

Anturane Pharmacology

Sulfinpyrazone, although less effective than allopurinol in reducing serum uric acid levels, remains useful for the prevention or reduction of the joint changes and tophus deposition that would otherwise occur in chronic gout; it has no antiinflammatory properties. During the initial period of sulfinpyrazone use, acute attacks of gout may increase in frequency and severity. It is recommended, therefore, that either colchicine or a nonsteroidal antiinflammatory agent be coadministered during early sulfinpyrazone therapy. Abdominal pain, nausea, and possible reactivation of peptic ulcer have been reported.

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