ISOXICAM
- Product Name
- ISOXICAM
- CAS No.
- 34552-84-6
- Chemical Name
- ISOXICAM
- Synonyms
- Pacyl;W 8495;Maxicam;Vectren;ISOXICAM;Isoxicamo;Isoxicamum;)-,1,1-dioxide;pacyl(antiinflammatory);Inhibitor,Cyclooxygenase,COX,inhibit,Isoxicam
- CBNumber
- CB8101486
- Molecular Formula
- C14H13N3O5S
- Formula Weight
- 335.34
- MOL File
- 34552-84-6.mol
ISOXICAM Property
- 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
- WGK Germany
- 2
- RTECS
- DL0703000
- Toxicity
- LD50 in rats (mg/kg): >5000 orally (Whitehouse)
N-Bromosuccinimide Price
- Product number
- I1762
- Product name
- Isoxicam
- Purity
- analytical standard
- Packaging
- 1g
- Price
- $102
- Updated
- 2024/03/01
- Product number
- I918145
- Product name
- Isoxicam
- Packaging
- 1g
- Price
- $185
- Updated
- 2021/12/16
- Product number
- 452790
- Product name
- Isoxicam
- Packaging
- 1g
- Price
- $460
- Updated
- 2021/12/16
- Product number
- I918145
- Product name
- Isoxicam
- Packaging
- 10g
- Price
- $1455
- Updated
- 2021/12/16
- Product number
- CS-4726
- Product name
- Isoxicam
- Purity
- 99.11%
- Packaging
- 100mg
- Price
- $527
- Updated
- 2021/12/16
ISOXICAM Chemical Properties,Usage,Production
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 T1/2 (>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 A non-steroidal anti-inflammatory drug, it was withdrawn from the market in the 1980s following its association with cases of Steve s-Johnson syndrome.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].