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Nimesulide
"Descrizione"
by CarPas (5225 pt)
2023-Sep-11 11:01

Review Consensus: 10 Rating: 10 Number of users: 1
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Nimesulide is a chemical compound, sulphonamide.

It occurs in the form of a yellow powder. Stable. Incompatible with strong oxidising agents.

What it is used for and where

Medicine

Take only under medical supervision

Non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties, launched in 1985 in Italy and marketed in more than 50 countries worldwide with relatively low risk of gastrointestinal side effects. Not available in the United States.

Brief history

Nimesulide was reported to be hepatotoxic in 1997 and its use was restricted or banned in 2002 first in Finland and then in Spain due to the high frequency of associated hepatotoxicity (1). However, several studies have downgraded the problem and the European Medicines Agency (2), after an extensive study, recognised its efficacy in

  • intense pain
  • dysmenorrhoea
  • pain from osteoarthritis 
  • pain from traumatic sprains and tendinitis

taking into account the risk/benefit ratio, only recommended a maximum daily dose for the 100mg dose. Stricter restrictions apply to the 200mg dose. 

An important study from 2010 clarifies the risk/benefit ratio comprehensively: "Results suggest that implementation of regulatory actions regarding nimesulide may have prevented 79 admissions for liver damage, but increased admissions for UGIB by 859 cases."

Nimesulide as a preferential inhibitor of cyclooxygenase-2 could play a potential therapeutic role in the management of patients with cerebral ischaemia (4) and, together with silver complexes, a potential and safe agent for the topical treatment of skin cancer in humans (5).

Antidiabetic activity of Nimesulide has also been demonstrated (6).

However, recently, a study by Brazilian, Spanish and Argentinean researchers reiterated, this time negatively, the risk/benefit ratio of Nimesulide (7).  Frankly, from the consumer's point of view, it is difficult to make a choice since the same doctors give opposite opinions.

Like all drugs it can cause side effects. Always ask the physician.

For more information:    Nimesulide studies


AppearanceYellow powder
Boiling Point
442.0±55.0 °C at 760 mmHg
Melting Point
140-146°C
Flash Point
221.1±31.5°C
Density1.5±0.1 g/cm3
Vapour Pressure
0.0±1.1 mmHg at 25°C
Index of Refraction
1.638
PSA109.60000
LogP3.79
Safety


  • Molecular Formula  C13H12N2O5S
  • Linear Formula   CH3(CH2)3CH(C2H5)CH2O2CCH2CH(SO3Na)CO2CH2CH(C2H5)(CH2)3CH3
  • Molecular Weight     308.31
  • Exact Mass   308.046692
  • CAS  51803-78-2
  • UNII    V4TKW1454M
  • EC Number   257-431-4
  • DSSTox Substance ID  DTXSID3037250
  • IUPAC  N-(4-nitro-2-phenoxyphenyl)methanesulfonamide
  • InChI=1S/C13H12N2O5S/c1-21(18,19)14-12-8-7-10(15(16)17)9-13(12)20-11-5-3-2-4-6-11/h2-9,14H,1H3  
  • InChl Key    HYWYRSMBCFDLJT-UHFFFAOYSA-N  
  • SMILES   CS(=O)(=O)NC1=C(C=C(C=C1)[N+](=O)[O-])OC2=CC=CC=C2
  • MDL number  MFCD00012455
  • PubChem Substance ID    24859403
  • ChEBI  44445
  • RTECS   PB0970000
  • NCI   C29842

Synonyms

  • Aulin
  • Mesulid
  • Flogovital
  • Nisulid
  • Sulidene
  • Methanesulfonamide, N-(4-nitro-2-phenoxyphenyl)-
  • Nimed
  • Aldoron
  • Nise Gel
  • Nimedex
  • Prestwick_618
  • Orthobid

References_________________________________________________________________________

(1) Bessone, F., Fay, F., Fay, O., Vorobioff, J., Passamonti, M. E., Godoy, A., & Tanno, H. (1997, October). Nimesulide hepatotoxicity. In Hepatology (Vol. 26, No. 4, pp. 1417-1417). INDEPENDENCE SQUARE WEST CURTIS CENTER, STE 300, PHILADELPHIA, PA 19106-3399: WB SAUNDERS CO.

(2) epar.P.Nimesulide .EMEA-CPMP-1724-04-en-Final.doc (europa.eu) 

(3) Venegoni M, Da Cas R, Menniti-Ippolito F, Traversa G. Effects of the European restrictive actions concerning nimesulide prescription: a simulation study on hepatopathies and gastrointestinal bleedings in Italy. Ann Ist Super Sanita. 2010;46(2):153-7. doi: 10.4415/ANN_10_02_08. 

(4) Candelario-Jalil E. Nimesulide as a promising neuroprotectant in brain ischemia: new experimental evidences. Pharmacol Res. 2008 Apr;57(4):266-73. doi: 10.1016/j.phrs.2008.03.003. 

(5) Candido TZ, de Paiva REF, Figueiredo MC, de Oliveira Coser L, Frajácomo SCL, Abbehausen C, Cardinalli IA, Lustri WR, Carvalho JE, Ruiz ALTG, Corbi PP, Lima CSP. Silver Nimesulide Complex in Bacterial Cellulose Membranes as an Innovative Therapeutic Method for Topical Treatment of Skin Squamous Cell Carcinoma. Pharmaceutics. 2022 Feb 21;14(2):462. doi: 10.3390/pharmaceutics14020462.

(6) Joharapurkar A, Kshirsagar S, Patel V, Patel M, Savsani H, Jain M. In vivo antidiabetic activity of nimesulide due to inhibition of amino acid transport. Basic Clin Pharmacol Toxicol. 2022 Jan;130(1):35-43. doi: 10.1111/bcpt.13670. 

(7) Colombato L, Arrese M, Reggiardo MV, Ono SK, Carrilho F, Lucena MI, Andrade RJ. Serious liver injury induced by Nimesulide: an international collaborative study. Arch Toxicol. 2021 Apr;95(4):1475-1487. doi: 10.1007/s00204-021-03000-8. 

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