ISOXICAM Chemical Properties

Melting point:

265-271℃

Density 

1.588

storage temp. 

-20°C Freezer

solubility 

Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)

pka

4.50±1.00(Predicted)

color 

White to Pale Beige

Safety Information

WGK Germany 

2

RTECS 

DL0703000

Toxicity

LD50 in rats (mg/kg): >5000 orally (Whitehouse)

MSDS

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ISOXICAM Usage And Synthesis

Description

Isoxicam is a non-steroidal antiinflammatory agent useful in the treatment of various forms of rheumatoid arthritis, osteoarthritis and musculoskeletal disorders. It is about one-tenth as potent as its structural relative sudoxicam; its similar long T_1/2 (>30 hrs.) allows once-daily dosing.

Originator

Warner-Lambert (USA)

Uses

antiseborrheic

Uses

Isoxicam is used for the same indications as piroxicam. Synonyms for isoxicam are floxicam and maxicam.

Uses

Isoxicam is a potent, orally active, nonsteroidal anti-inflammatory drug.

Definition

ChEBI: A monocarboxylic acid amide that is piroxicam in which the pyrid-2-yl group is replaced by a 5-methyl-1,2-oxazol-3-yl group. A non-steroidal anti-inflammatory drug, it was withdrawn from the market in the 1980s following its association with cases of Steve s-Johnson syndrome.

Manufacturing Process

A mixture of 40.5 g (0.15 mol) of 3-carbethoxy-4-hydroxy-2-methyl-2H-1,2- benzothiazine 1,1-dioxide, 20.6 g (0.21 mol) of 3-amino-5-methylisoxazole, and 2,500 ml of xylene was refluxed for 24 hours in a Soxhlet apparatus, the thimble of which contained 60 g of Linde type 4A molecular sieve. The mixture was cooled to 25°C and the resulting crystalline precipitate was collected and washed with ether to give 44 g of crude product. Recrystallization from 1,600 ml of 1,4-dioxan gave 34.7 g of material, MP 265°C to 271°C dec.

brand name

Maxicam (Parke-Davis);Floxicam;PACYL.

Therapeutic Function

Antiinflammatory

World Health Organization (WHO)

Isoxicam, a nonsteroidal anti-inflammatory agent, was introduced in 1983 for the treatment of rheumatic disorders. By 1985 its use had been associated with serious adverse effects, including four deaths from rare skin reactions. This led to its withdrawal in France followed immediately by the voluntary suspension of marketing worldwide by the major manufacturer.

Clinical Use

Isoxicam is a nonsteroidal anti-inflammatory drug withdrawn from the market as a consequence of reports of fatal skin reaction.

Synthesis

Isoxicam, 1,1-dioxide 4-hydroxy-2-methyl-N-(5-methyl-3-isoxazolyl)-2H-1,2- benzothiazine-3-carboxamide (3.2.80), is synthesized analogous to piroxicam, using amidation of 1,1-dioxide 3-methoxycarbonyl-3,4-dihydro-2-H-1,2-benzothiazine-4-one (3.2.78) in the last stage with 3-amino-5-methylisoxazole, instead of 2-aminopyridine [127¨C130].

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