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| CAS No.: | 51803-78-2 |
|---|---|
| Name: | Nimesulide |
| Molecular Structure: | |
|
|
|
| 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: |
 Xn,  Xi
|
| Risk Codes: | 22-36/37/38 |
| Safety: | 36-26 |
| Transport Information: | UN 2811 6 |
| PSA: | 109.60000 |
| LogP: | 4.43560 |
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- 51803-78-2
nimesulide
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water pH=~ 2; | 100% |
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| In N,N-dimethyl-formamide at 25℃; pH=9.0; Kinetics; Disproportionation; |
- 51765-51-6
N-(2-Phenoxyphenyl)-methansulfonamid
- 51803-78-2
nimesulide
| Conditions | Yield |
|---|---|
| With sulfuric acid; nitric acid; acetic acid for 1h; Activation energy; Temperature; |
- 121-88-0
2-Amino-5-nitrophenol
- 51803-78-2
nimesulide
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 |
- 51803-78-2
nimesulide
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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
| Conditions | Yield |
|---|---|
| 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% |
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Chemistry
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IUPAC Name: N-(4-Nitro-2-phenoxyphenyl)methanesulfonamide
Molecular Formula: C13H12N2O5S
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 cm3
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): 
Xn,
Xi
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.