Nimesulid

Nimesulid
ATC Code M01AX17, M02AA26
Formula C13H12N2O5S
Molar Mass (g·mol−1) 308,31
Physical State solid
Melting Point (°C) 143–144,5
CAS Number 51803-78-2
PUB Number 4495
Drugbank ID DB04743
Solubility practically insoluble in water

Basics

Nimesulide is a non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. Its approved indications are the treatment of acute pain, symptomatic treatment of osteoarthritis and primary dysmenorrhea in adolescents and adults over 12 years of age. It is usually taken by mouth.

Pharmacology

Pharmacodynamics

The anti-inflammatory effect of nimesulide is due to the inhibition of cyclooxygenase-2 (COX-2), an enzyme involved in prostaglandin synthesis via the arachidonic acid pathway. This results in decreased levels of prostaglandins that mediate pain, fever, and inflammation.

Pharmacokinetics

Nimesulide is rapidly absorbed after oral administration. Nimesulide has a relatively rapid onset of action, with significant reductions in pain and inflammation observed within 15 minutes of drug ingestion. Plasma protein binding is greater than 97%. Nimesulide undergoes extensive biotransformation, primarily to 4-hydroxynimesulide. 4-Hydroxynimesulide is also biologically active. Elimination is largely renal and to a lesser extent fecal. The half-life of nimesulide is 2-4 hours.

Toxicity

Side effects

Due to concerns about the risk of liver toxicity, nimesulide has been withdrawn from the market in several countries (Spain, Finland, Belgium, Ireland and the USA). Liver problems have led to both deaths and the need for transplantation. This can occur as early as three days after starting the drug.

Folgende Nebenwirkungen sind ebenfalls aufgetreten:

  • Diarrhea
  • Vomiting
  • Skin rash
  • itching
  • dizziness
  • Bitter taste in the mouth

Toxicological data

LD50 (rat, oral): 200 mg-kg-1

Sources

  • Drugbank
  • PubChem
  • Aktories, Förstermann, Hofmann, Starke: Allgemeine und spezielle Pharmakologie und Toxikologie, Elsvier, 2017
Markus Falkenstätter

Markus Falkenstätter
Author

Markus Falkenstätter ist Autor zu pharmazeutischen Themen in der Medizin-Redaktion von Medikamio. Er befindet sich im letzten Semester seines Pharmaziestudiums an der Universität Wien und liebt das wissenschaftliche Arbeiten im Bereich der Naturwissenschaften.

Mag. pharm Stefanie Lehenauer

Mag. pharm Stefanie Lehenauer
Lector

Stefanie Lehenauer ist seit 2020 freie Autorin bei Medikamio und studierte Pharmazie an der Universität Wien. Sie arbeitet als Apothekerin in Wien und ihre Leidenschaft sind pflanzliche Arzneimittel und deren Wirkung.

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