Nimesulide

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Structural formula
Structure of nimesulfide
General
Non-proprietary name Nimesulide
other names
  • N - (4-nitro-2-phenoxyphenyl) methanesulfonamide ( IUPAC )
  • Nimesulidum ( Latin )
Molecular formula C 13 H 12 N 2 O 5 S
Brief description

yellowish, crystalline and polymorphic powder

External identifiers / databases
CAS number 51803-78-2
EC number 257-431-4
ECHA InfoCard 100.052.194
PubChem 4495
ChemSpider 4339
DrugBank DB04743
Wikidata Q20994
Drug information
ATC code

M01 AX17

Drug class

Non-steroidal anti-inflammatory drug

Mechanism of action

Cyclooxygenase - inhibitor

properties
Molar mass 308.31 g · mol -1
Physical state

firmly

Melting point

143-144.5 ° C

solubility
  • practically insoluble in water (26.9 mg l −1 at 25 ° C), poor in ethanol
  • good in acetone
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 301
P: 301 + 310
Toxicological data

200 mg kg −1 ( LD 50 ,  rat ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nimesulide (trade name: Aulin (CH) / Nisulid (CH)) is an antipyretic, anti-inflammatory and analgesic drug . The active ingredient is one of the non-steroidal anti-inflammatory drugs.

It selectively inhibits COX-2 around 13 times more than COX-1 . In addition, it suppresses the formation of oxidants such as free oxygen radicals or hypochlorous acid . This effect contributes to the anti-inflammatory effect, as certain radicals cause direct cell damage and inactivate protease inhibitors. Nimesulide also inhibits the release of histamine from mast cells and basophils.

Nimesulide also reduces the neutrophil- mediated destruction of the cartilage matrix during an inflammatory response.

Side effects

The most common undesirable effects include digestive problems such as diarrhea, nausea, vomiting, and increases in liver enzymes. Drowsiness, high blood pressure, shortness of breath, constipation, flatulence, inflammation of the gastric mucosa, itching, rash, increased sweating and edema have also been observed occasionally. Serious liver damage (including fatal cases), inflammation of the liver, jaundice and cholestasis have occurred very rarely.

Individual evidence

  1. ↑ a b c European Pharmacopoeia Commission (Ed.): EUROPÄISCHE PHARMACOPÖE 5th EDITION . tape 5.0-5.8 , 2006.
  2. ↑ a b c Entry on nimesulide in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  3. ↑ a b Data sheet Nimesulide from Sigma-Aldrich , accessed on April 16, 2011 ( PDF ).
  4. ↑ HH Tan, WM Ong, SH Lai, WC Chow: Nimesulide-induced hepatotoxicity and fatal hepatic failure. In: Singapore medical journal. Volume 48, Number 6, June 2007, pp. 582-585, PMID 17538762 . ( PDF ).

Web links

  • Entry on nimesulide at Vetpharm, accessed June 23, 2012.

literature

  • Hermann Hager, Franz von Bruchhausen (ed.): Handbook of Pharmaceutical Practice , Volume 5, Materials LZ, Springer 1999, ISBN 3-540-62646-8 , pp. 320–323.