Sulfinpyrazone - Misplaced Pages

Chemical compound

Pharmaceutical compound

Sulfinpyrazone
Clinical data

Trade names	Anturan, Anturane, Apo-sulfinpyrazone
AHFS/Drugs.com	Monograph
MedlinePlus	a682339
Routes of administration	By mouth intravenous
ATC code	M04AB02 (WHO)
Pharmacokinetic data
Protein binding	98–99%
Metabolism	liver
Excretion	kidney
Identifiers
IUPAC name 1,2-diphenyl-4-pyrazolidine-3,5-dione
CAS Number	57-96-5
PubChem CID	5342
IUPHAR/BPS	5826
DrugBank	DB01138
ChemSpider	5149
UNII	V6OFU47K3W
KEGG	D00449
ChEBI	CHEBI:9342
ChEMBL	ChEMBL832
CompTox Dashboard (EPA)	DTXSID0023618
ECHA InfoCard	100.000.325
Chemical and physical data
Formula	C₂₃H₂₀N₂O₃S
Molar mass	404.48 g·mol
3D model (JSmol)	Interactive image
SMILES O=C2N(c1ccccc1)N(C(=O)C2CCS(=O)c3ccccc3)c4ccccc4
InChI InChI=1S/C23H20N2O3S/c26-22-21(16-17-29(28)20-14-8-3-9-15-20)23(27)25(19-12-6-2-7-13-19)24(22)18-10-4-1-5-11-18/h1-15,21H,16-17H2 Key:MBGGBVCUIVRRBF-UHFFFAOYSA-N
(verify)

Sulfinpyrazone is a uricosuric medication used to treat gout. It also sometimes is used to reduce platelet aggregation by inhibiting degranulation of platelets which reduces the release of ADP and thromboxane.

Like other uricosurics, sulfinpyrazone works by competitively inhibiting uric acid reabsorption in the proximal tubule of the kidney.

Contraindications

Sulfinpyrazone must not be used in persons with renal impairment or a history of uric acid kidney stones.

Research

Trial have found that, Sulfinpyrazone taken in specific daily dose immediately following a patient having suffered from a myocardial infarction seem to drastically reduce the incidence of sudden death by as much as 43% and cardiac mortality by 32% in the 24 months following their heart attack.

References

Underwood M (June 2006). "Diagnosis and management of gout". BMJ. 332 (7553): 1315–9. doi:10.1136/bmj.332.7553.1315. PMC 1473078. PMID 16740561.
Anturane Reinfarction Trial Research Group (1980-01-31). "Sulfinpyrazone in the Prevention of Sudden Death after Myocardial Infarction". New England Journal of Medicine. 302 (5): 250–256. doi:10.1056/NEJM198001313020502. ISSN 0028-4793. PMID 6985706.

v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone
salicylates	Aspirin (acetylsalicylic acid) Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen Carprofen Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen Ibuproxam Indoprofen Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin Tiaprofenic acid Vedaprofen Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib Deracoxib Etoricoxib Firocoxib Lumiracoxib Mavacoxib Parecoxib Robenacoxib Rofecoxib Valdecoxib
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; WHO-Essential Medicines; withdrawn drugs; veterinary use.
category [REDACTED] commons portal

Drugs used for gout (M04)

Uricosurics

primary	Probenecid Sulfinpyrazone Benzbromarone Isobromindione
secondary	Amlodipine Atorvastatin Fenofibrate Guaifenesin Lesinurad Losartan

Xanthine oxidase inhibitors

purine analogues	Allopurinol Oxypurinol Tisopurine
other	Febuxostat Inositols (Phytic acid Myo-inositol) Topiroxostat

Mitotic inhibitors

Colchicine

Other

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

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