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51803-78-2

Basic Information
CAS No.: 51803-78-2
Name: Nimesulide
Article Data: 10
Molecular Structure:
Molecular Structure of 51803-78-2 (Nimesulide)
Formula: C13H12N2O5S
Molecular Weight: 308.315
Synonyms: 4'-Nitro-2'-phenoxymethansulfonanilid;Methanesulfonamide,N-(4-nitro-2-phenoxyphenyl)-;4-Nitro-2-phenoxy-methanesulfonanilide;Aulin;Flogovital;N-(4-Nitro-2-phenoxyphenyl)methanesulfonamide;
EINECS: 257-431-4
Density: 1.451 g/cm3
Melting Point: 140-146 °C
Boiling Point: 442 °C at 760 mmHg
Flash Point: 221.1 °C
Solubility: Soluble in water (<50 µg/ml), 1:10 DMSO:PBS (pH 7.2) (<200 µg/ml), ethanol (1 mg/ml), DMSO (15 mg/ml), DMF (15 mg/ml), chloroform, dichloromethane, acetone (freely soluble), and 1N NaOH.
Appearance: Yellow Needle-Like Crystals
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22-36/37/38
Safety: 36-26
Transport Information: UN 2811 6
PSA: 109.60000
LogP: 4.43560
Synthetic route

sodium N-(methylsulfonyl)-N-(4-nitro-2-phenoxyphenyl)sulfamate

51803-78-2

nimesulide

Conditions
ConditionsYield
With hydrogenchloride In water pH=~ 2;100%
5422-92-4

1-amino-2-phenoxy-4-nitrobenzene

124-63-0

methanesulfonyl chloride

51803-78-2

nimesulide

Conditions
ConditionsYield
Stage #1: 1-amino-2-phenoxy-4-nitrobenzene; methanesulfonyl chloride With triethylamine In dichloromethane at 20℃; for 23h; Cooling with ice;
Stage #2: With sodium hydroxide In water for 16h; Reflux;
74.3%

nimesulide radical anion

A

51803-78-2

nimesulide

B

4-nitrosonimesulide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 25℃; pH=9.0; Kinetics; Disproportionation;
51765-51-6

N-(2-Phenoxyphenyl)-methansulfonamid

51803-78-2

nimesulide

Conditions
ConditionsYield
With sulfuric acid; nitric acid; acetic acid for 1h; Activation energy; Temperature;
121-88-0

2-Amino-5-nitrophenol

51803-78-2

nimesulide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: acetic acid / Reflux
2.1: copper diacetate; pyridine N-oxide; pyridine; oxygen / dichloromethane / 72 h / 20 °C / Molecular sieve
3.1: hydrazine hydrate / methanol / 6 h / Reflux
4.1: triethylamine / dichloromethane / 23 h / 20 °C / Cooling with ice
4.2: 16 h / Reflux
View Scheme
117346-07-3

2-(2-hydroxy-4-nitrophenyl)isoindoline-1,3-dione

51803-78-2

nimesulide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: copper diacetate; pyridine N-oxide; pyridine; oxygen / dichloromethane / 72 h / 20 °C / Molecular sieve
2.1: hydrazine hydrate / methanol / 6 h / Reflux
3.1: triethylamine / dichloromethane / 23 h / 20 °C / Cooling with ice
3.2: 16 h / Reflux
View Scheme

2-(4-nitro-2-phenoxyphenyl)isoindoline-1,3-dione

51803-78-2

nimesulide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrazine hydrate / methanol / 6 h / Reflux
2.1: triethylamine / dichloromethane / 23 h / 20 °C / Cooling with ice
2.2: 16 h / Reflux
View Scheme
51803-78-2

nimesulide

51765-60-7

N-(4-amino-2-phenoxy phenyl) methanesulfonamide

Conditions
ConditionsYield
With 5% Pd(II)/C(eggshell); hydrogen In ethyl acetate at 27℃; for 3h;100%
With hydrogenchloride; tin In water at 90℃; for 3h;100%
With hydrogen; palladium on activated charcoal In ethanol Ambient temperature;97%
51803-78-2

nimesulide

74-88-4

methyl iodide

51765-67-4

N-Methyl-N-(4-nitro-2-phenoxy-phenyl)-methanesulfonamide

Conditions
ConditionsYield
Stage #1: nimesulide With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere;
Stage #2: methyl iodide In N,N-dimethyl-formamide at 0 - 20℃; for 12h; Inert atmosphere;
99%
With potassium carbonate In acetonitrile for 5h;77%
51803-78-2

nimesulide

C13H10(2)H2N2O5S

Conditions
ConditionsYield
With [(1,5-cyclooctadiene)Ir(1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)(PPh3)]PF6; deuterium In dichloromethane at 20℃; for 2h; Sealed tube;96%
Raw Materials
51765-51-6
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Chemistry


IUPAC Name: N-(4-Nitro-2-phenoxyphenyl)methanesulfonamide
Molecular Formula: C13H12N2O5
Molecular Weight: 308.31 g/mol
Canonical SMILES: c1(c(ccc(c1)[N+](=O)[O-])NS(C)(=O)=O)Oc1ccccc1
InChI: InChI=1/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
EINECS: 257-431-4
Classification Code: Analgesics; Analgesics, Non-Narcotic; Anti-Inflammatory Agents; Anti-inflammatory agents, non-steroidal; Antirheumatic Agents; Cyclooxygenase inhibitors; Drug / Therapeutic Agent; Enzyme Inhibitors; Human Data; Peripheral Nervous System Agents; Sensory System Agents
Product Categories: Active Pharmaceutical Ingredients; All Inhibitors;Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals
Stability: Stable. Incompatible with strong oxidizing agents.
Index of Refraction: 1.638 
Molar Refractivity: 76.32 cm3 
Molar Volume: 212.3 cm3 
Polarizability: 30.25×10-24 cm
Surface Tension: 62 dyne/cm 
Density:  1.451 g/cm3 
Flash Point: 221.1 °C 
Enthalpy of Vaporization: 69.94 kJ/mol 
Boiling Point: 442 °C at 760 mmHg 
Melting Point: 140-146 °C
Storage temperature: 2-8 °C
Vapour Pressure of Nimesulide (CAS NO.51803-78-2): 5.19E-08 mmHg at 25 °C

History

  Nimesulide (CAS NO.51803-78-2) was launched in Italy for the first time as Aulin and Mesulid in 1985. It has become a leading non-steroidal anti-inflammatory drug in over 50 countries worldwide. In 2002 nimesulide benefit/risk profile was reviewed by the EMEA following decision to temporarily suspend the drug from the market in March 2002.
Due to concerns about the risk of hepatotoxicity, nimesulide has been withdrawn from market in many countries.

Uses

  Nimesulide (CAS NO.51803-78-2) is a relatively COX-2 selective, non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. Its approved indications are the treatment of acute pain, the symptomatic treatment of osteoarthritis and primary dysmenorrhoea in adolescents and adults above 12 years old.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 100mg/kg/5W-I (100mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

LIVER: "JAUNDICE, CHOLESTATIC"

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Journal of Hepathology. Vol. 29, Pg. 135, 1998.
mouse LD50 intraperitoneal 216mg/kg (216mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 17, Pg. 1254, 1975.
mouse LD50 oral 392mg/kg (392mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 17, Pg. 1254, 1975.
rat LD50 intraperitoneal 163mg/kg (163mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 17, Pg. 1254, 1975.
rat LD50 oral 200mg/kg (200mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 34, Pg. 759, 1975.
women TDLo oral 2mg/kg (2mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

KIDNEY, URETER, AND BLADDER: PROTEINURIS
Nephrology, Dialysis, Transplantation. Vol. 12, Pg. 1493, 1997.
women TDLo oral 84mg/kg/3W-I (84mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL"

BLOOD: EOSINOPHILIA
Journal of Hepathology. Vol. 29, Pg. 135, 1998.
women TDLo unreported 8mg/kg (8mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHANGE IN FUNCTION: TASTE

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Allergy. Vol. 52(Suppl,

Safety Profile

Hazard Codes of Nimesulide (CAS NO.51803-78-2): HarmfulXn,IrritantXi
Risk Statements: 22-36/37/38 
R22: Harmful if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 36-26 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS of Nimesulide (CAS NO.51803-78-2): PB0970000

Specification

 Nimesulide (CAS NO.51803-78-2), its Synonyms are 4'-Nitro-2'-phenoxymethansulfonanilid ; 4-Nitro-2-phenoxy-methanesulfonanilide ; Aulin ; Flogovital ; Mesulid ; N-(4-Nitro-2-phenoxyphenyl)methanesulfonamide ; Nimed ; Nimesulida ; Methanesulfonamide, N-(4-nitro-2-phenoxyphenyl)- (9CI) ; Methanesulfonanilide, 4'-nitro-2'-phenoxy- . It is yellow needle-like crystals.