Sulfinpyrazone

Chemical compound

M04AB02 (WHO)

Pharmacokinetic dataProtein binding98–99%MetabolismliverExcretionkidneyIdentifiers

IUPAC name

1,2-diphenyl-4-[2-(phenylsulfinyl)ethyl]pyrazolidine-3,5-dione

CAS Number

57-96-5^Y

PubChem CID

5342

IUPHAR/BPS

5826

DrugBank

DB01138^Y

ChemSpider

5149^Y

UNII

V6OFU47K3W

KEGG

D00449^Y

ChEBI

CHEBI:9342^Y

ChEMBL

ChEMBL832^Y

CompTox Dashboard (EPA)

DTXSID0023618

ECHA InfoCard100.000.325

Chemical and physical dataFormulaC₂₃H₂₀N₂O₃SMolar mass404.48 g·mol⁻¹3D 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^Y
Key:MBGGBVCUIVRRBF-UHFFFAOYSA-N^Y

(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.^[1]

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. ^[2]

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.

Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)

pyrazolones /
pyrazolidines

salicylates

acetic acid derivatives
and related substances

oxicams

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)

COX-2 inhibitors
(coxibs)

other

NSAID
combinations

Key: underline indicates initially developed first-in-class compound of specific group; ^#WHO-Essential Medicines; ^†withdrawn drugs; ^‡veterinary use.