Ampiroxicam Chemical Properties

Melting point:

159-161?C

Density 

1.44±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

12.74±0.20(Predicted)

color 

White to Off-White

CAS DataBase Reference

99464-64-9(CAS DataBase Reference)

Safety Information

Toxicity

LD50 orally in male, female rats: 1798, 747 mg/kg (Iijima)

Ampiroxicam Usage And Synthesis

Description

Ampiroxicam is a once-daily non-steroidal anti-inflammatory drug (NSAID) introduced in Japan. As a non-acidic ether carbonate prodrug of the widely used antiinflammatory agent, piroxicam, ampiroxicam is similar or more potent than piroxicam in suppressing carrageenan edema, ultraviolet erythema, traumatic edema, capillary permeability, acetic acid writhing, yeast algesia and yeast hyperthermia in many animals. Eioavailability studies in man show undetectable plasma levels of ampiroxicam indicating 100% conversion to piroxicam during absorption process. Ampiroxicam has been reported to have fewer side effects on the gastric mucosa than piroxicam.

Chemical Properties

White Solid

Originator

Pflzer (Japan)

Uses

Prodrug of Piroxicam. Anti-inflammatory.

Uses

antiinflammatory, analgesic

Definition

ChEBI: A benzothiazine that is the 1-[(ethoxycarbonyl)oxy]ethyl ether of piroxicam. A prodrug for piroxicam, it is used for the relief of pain and inflammation in musculoskeletal disorders such as rheumatoid arthritis and osteoarthritis.

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.

brand name

Nacyl; Flucam

Therapeutic Function

Antiinflammatory

Ampiroxicam(99464-64-9)Related Product Information

• Basic Violet 1
• Methyl acrylate
• Chlorantraniliprole
• Methyl acetate
• Paraquat dichloride
• Methylparaben
• N,N-Dimethylformamide
• Acetonitrile
• Methanol
• Benzamide
• Kresoxim-methyl
• Formamide,Deionized
• Formamide
• Piroxicam
• Methyl
• Meloxicam
• Tenoxicam
• Lornoxicam