99464-64-9

Basic information

• Product Name: Ampiroxicam
• Synonyms: 4-[1-(ethoxycarbonyloxy)ethoxy]-2-methyl-n-(2-pyridyl)-2h-1,2-benzothiazine-3-carboxamide-1,1-dioxide;AMPIROXICAM;carbonicacid,ethyl1-((2-methyl-3-((2-pyridinylamino)carbonyl)-2h-1,2-benzoth;iazin-4-yl)oxy)ethylester,s,s-dioxide;2H-1,2-Benzothiazine, carbonic acid deriv.;Carbonic acid, ethyl 1-[[2-methyl-1,1-dioxido-3-[(2-pyridinylamino)carbonyl]-2H-1,2-benzothiazin-4-yl]oxy]ethyl ester;Carbonic acid, ethyl 1-[[2-methyl-3-[(2-pyridinylamino)carbonyl]-2H-1,2-benzothiazin-4-yl]oxy]ethyl ester, S,S-dioxide;CP 65703
• CAS NO: 99464-64-9
• Molecular Formula: C20H21N3O7S
• Molecular Weight: 447.46
• EINECS: 1308068-626-2
• Product Categories: Activators;API;FLUCAM;Inhibitors
• Mol File: 99464-64-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 159-161?C
• Appearance: Powder
• Density: 1.44 g/cm³
• Refractive Index: 1.629
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.74±0.20(Predicted)
• CAS DataBase Reference: Ampiroxicam(CAS DataBase Reference)
• NIST Chemistry Reference: Ampiroxicam(99464-64-9)
• EPA Substance Registry System: Ampiroxicam(99464-64-9)

Safety Data

• Hazardous Substances Data: 99464-64-9(Hazardous Substances Data)

Usage

Description

Ampiroxicam is a once-daily non-steroidal anti-inflammatory drug (NSAID) introduced in Japan. It is a non-acidic ether carbonate prodrug of the widely used anti-inflammatory agent, piroxicam. Ampiroxicam is similar or more potent than piroxicam in suppressing various inflammation-related conditions in animals. It has been reported to have fewer side effects on the gastric mucosa than piroxicam. As a benzothiazine, it is the 1-[(ethoxycarbonyl)oxy]ethyl ether of piroxicam and is used for the relief of pain and inflammation in musculoskeletal disorders.

Uses

Used in Pharmaceutical Industry:
Ampiroxicam is used as a prodrug for piroxicam, a widely used anti-inflammatory agent. It is employed for the relief of pain and inflammation in musculoskeletal disorders such as rheumatoid arthritis and osteoarthritis. Ampiroxicam is used for its potent anti-inflammatory properties and its ability to have fewer side effects on the gastric mucosa compared to piroxicam.
Used in Anti-inflammatory Applications:
Ampiroxicam is used as an anti-inflammatory agent for suppressing various inflammation-related conditions in animals, such as carrageenan edema, ultraviolet erythema, traumatic edema, capillary permeability, acetic acid writhing, yeast algesia, and yeast hyperthermia. Its potency is similar or greater than that of piroxicam, making it a valuable alternative for managing inflammation.
Brand Names:
Ampiroxicam is marketed under the brand names Nacycl and Flucam.

Originator

Pflzer (Japan)

Manufacturing Process

To a round bottomed flask equipped with a reflux condenser and stirring bar were added 2-methyl-N-(2-pyridyl)-4-hydroxy-2H-1,2-benzodiazine-3- carboxamide 1,1-dioxide (piroxicam, 10.0 g, 30.2 mmol), potassium carbonate (8.35 g, 60.4 mmol), α-chloroethyl ethyl carbonate (12.35 mL, 13.81 g, 90.6 mmol) and acetone (350 mL). The heterogenous reaction mixture was heated to reflux under a nitrogen atmosphere. After 19 hours, anhydrous sodium iodide (22.6 g, 150.7 mmol) was added and reflux continued for an additional 5 hours. The acetone was removed in vacuum leaving a brown residue which was treated with water (250 mL) and methylene chloride (250 mL). The organic layer was separated and the aqueous layer extracted with additional methylene chloride (250 mL). The combined organic extracts were washed with water (250 mL), brine (250 mL), dried (Na2SO4) and concentrated in vacuum to a brown oil. Column chromatography on silica gel (1:9 ethyl acetate:methylene chloride) afforded a pale yellow foam (10.67 g, 79.0%). The 4-[1-(ethoxycarbonyloxy)ethoxy]- 2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide was recrystallized from toluene to give 9.50 g of pure white crystals; melting point 159-161°C.

InChI:InChI=1/C20H21N3O7S/c1-4-28-20(25)30-13(2)29-18-14-9-5-6-10-15(14)31(26,27)23(3)17(18)19(24)22-16-11-7-8-12-21-16/h5-13H,4H2,1-3H3,(H,21,22,24)

Upstream product

• 50893-36-2 1-Chloroethyl ethyl carbonate 
• 36322-90-4 Piroxicam 

Relevant articles and documents

Deuterium Isotope Effects on Carbon-13 NMR Shifts and the Tautomeric Equilibrium in N-Substituted Pyridyl Derivatives of Piroxicam

N-Alkylated pyridyl derivatives of piroxicam are formally zwitterionic but can, at the expense of aromaticity in the pyridyl ring, revert to neutral structures by means of fast internal proton transfers.The large change in dipole moment accompanying these tautomeric shifts makes the equilibrium unusually sensitive to changes in chemical substitution, solvent, and temperature.This property is used to formulate, test, and verify a new type of deuterium isotope effect on carbon-13 NMR shifts recently proposed by Hansen and, in the process, establish close correspondencewith the general theory of isotope effects on proton transfer equilibria.