NIMESULIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H12N2O5S
Molecular Weight	308.31
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CS(=O)(=O)NC1=C(OC2=CC=CC=C2)C=C(C=C1)[N+]([O-])=O

InChI

InChIKey=HYWYRSMBCFDLJT-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB04743
Curator's Comment: description was created based on several sources, including http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Nimesulide_31/WC500125574.pdf

Nimesulide is a relatively COX-2 selective, non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. Its approved indications are the second line treatment of acute pain and primary dysmenorrhoea. Due to concerns about the risk of hepatotoxicity, nimesulide has been withdrawn from market in many countries.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-1 127 Target ID: CHEMBL221 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Nimesulide_31/WC500125574.pdf	Inhibitor 8297		17.4 µM [IC50]
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Nimesulide_31/WC500125574.pdf	Inhibitor 8297		0.6 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute pain 17 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Nimesulide_31/WC500125574.pdf	Primary		Approved 8429	Nimesulide Approved Use Treatment of acute pain. Primary dysmenorrhoea.
Primary dysmenorrhea 16 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Referrals_document/Nimesulide_31/WC500125574.pdf	Primary		Approved 8429	Nimesulide Approved Use Treatment of acute pain. Primary dysmenorrhoea.

PubMed

Title	Date	PubMed
Risk factors for acetaminophen and nimesulide intolerance in patients with NSAID-induced skin disorders.	1999 Jun	10400483
Nimesulide-induced hepatitis and acute liver failure.	1999 Oct	10731303
Leukotriene receptor antagonists may prevent NSAID-induced exacerbations in patients with chronic urticaria.	2000 Aug	10982225
Par-4, a proapoptotic gene, is regulated by NSAIDs in human colon carcinoma cells.	2000 Jun	10833474
Nimesulide, a balanced drug for the treatment of osteoarthritis.	2001	11296545
Introduction to "nimesulide: beyond COX-2".	2001	11296542
[Nimesulide-induced acute hepatitis].	2001 Apr	11333664
Corneal stimulation of MMP-1, -9 and uPA by platelet-activating factor is mediated by cyclooxygenase-2 metabolites.	2001 Aug	11840344
Quantification of nimesulide in human plasma by high-performance liquid chromatography/tandem mass spectrometry. Application to bioequivalence studies.	2001 Dec	11754119
Long-term glucose infusion increases arterial pressure in dogs with cyclooxygenase-2 inhibition.	2001 Feb	11230365
Etoricoxib (MK-0663): preclinical profile and comparison with other agents that selectively inhibit cyclooxygenase-2.	2001 Feb	11160644
Role of PGE(2) in protease-activated receptor-1, -2 and -4 mediated relaxation in the mouse isolated trachea.	2001 Jan	11156565
Protective role of cyclooxygenase inhibitors in the adverse action of passive cigarette smoking on the initiation of experimental colitis in rats.	2001 Jan 5	11137876
Identification and isolation of the cyclooxygenase-2 inhibitory principle in Isatis tinctoria.	2001 Jul	11488453
[Neonatal chronic kidney failure associated with cyclo-oxygenase-2 inhibitors administered during pregnancy].	2001 Jun	11455321
Inhibition of cervical ripening by local application of cyclooxygenase 2 inhibitor.	2001 Jun	11408855
Can a cyclo-oxygenase type-2 selective tocolytic agent avoid the fetal side effects of indomethacin?	2001 Mar	11281476
Selective inhibition of COX-2 in humans is associated with less gastrointestinal injury: a comparison of nimesulide and naproxen.	2001 Mar	11171823
Role of COX-2-derived metabolites in regulation of the renal hemodynamic response to norepinephrine.	2001 Nov	11592955
Lipopolysaccharide-mediated immobility in mice: reversal by cyclooxygenase enzyme inhibitors.	2001 Oct	11838318
Effects of a COX-2 preferential agent nimesulide on TNBS-induced acute inflammation in the gut.	2001 Oct	11820457
Pathogenetic role of cyclooxygenase-2 in hyperprostaglandin E syndrome/antenatal Bartter syndrome: therapeutic use of the cyclooxygenase-2 inhibitor nimesulide.	2001 Oct	11673754
Evaluation of skin sensitization potential of melatonin and nimesulide by murine local lymph node assay.	2001 Oct	11576826
CaR-mediated COX-2 expression in primary cultured mTAL cells.	2001 Oct	11553512
The MDR phenotype is associated with the expression of COX-2 and iNOS in a human hepatocellular carcinoma cell line.	2002 Apr	11915030
Randomized pilot study of nimesulide treatment in Alzheimer's disease.	2002 Apr 9	11940691
Evaluation of isolated case reports on hepatotoxicity.	2002 Feb	11936716
Nimesulide, a preferential cyclooxygenase 2 inhibitor, suppresses peroxisome proliferator-activated receptor induction of cyclooxygenase 2 gene expression in human synovial fibroblasts: evidence for receptor antagonism.	2002 Feb	11840453
Induction of the complement component C1qB in brain of transgenic mice with neuronal overexpression of human cyclooxygenase-2.	2002 Feb	11810182
Antipyretics in children.	2002 Jan	11876124
Possible ranitidine-induced cholestatic jaundice.	2002 Jan	11816250
Regulation of prostaglandin production in an immortalized human myometrial cell line by cytokines and non-steroidal anti-inflammatory drugs.	2002 Jan 10	11750956

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dosage is 100 mg twice daily and the maximum duration of treatment are 15 days with the shortest duration of treatment recommended.

Route of Administration: Oral

In Vitro Use Guide

Nimesulide (1-100 microM) inhibited platelet aggregation induced by adrenaline (20-200 microM). It also inhibited thromboxane A2 formation by platelets at low concentration (IC50 = 1 microM). However, much lower concentrations of nimesulide (0.01-0.1 microM) potentiated the aggregatory response of subthreshold concentrations of adrenaline (0.2-2 microM).

Name

Type

Language

NIMESULIDE

Official Name

English

NIMESULIDE [JAN]

Common Name

English

N-(4-NITRO-2-PHENOXYPHENYL)METHANESULFONAMIDE

Systematic Name

English

NIMESULIDE [MI]

Common Name

English

Nimesulide [WHO-DD]

Common Name

English

NIMESULIDE [EP IMPURITY]

Common Name

English

NSC-758412

Code

English

4'-NITRO-2'-PHENOXYMETHANESULFONANILIDE

Systematic Name

English

NIMESULIDE [EP MONOGRAPH]

Common Name

English

R-805

Code

English

nimesulide [INN]

Common Name

English

R 805

Code

English

NIMESULIDE [MART.]

Common Name

English

4-NITRO-2-PHENOXYMETHANESULFONANILIDE

Common Name

English

Classification Tree Code System Code

WHO-ATC

M02AA26