Structure via PubChem · Public domain (PubChem)
isoxicam
Sign in to saveAlso known as Maxicam, W-8495, N-(5-methyl-3-isoxazolyl)-4-hydroxy-2-methyl-2H-1,2-benzthiazine-3-carboxamide 1,1-dioxide, 4-hydroxy-3-(5-methyl-3-isoxazolylcarbamoyl)-2-methyl-2H-1,2-benzothiazine 1,1-dioxide, UNII-8XU734C4NG, EINECS 252-084-5, BRN 0577221, 4-hydroxy-2-methyl-N-(5-methyl-3-isoxazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide
Isoxicam is a nonsteroidal anti-inflammatory drug (NSAID) that was taken or applied to reduce inflammation and as an analgesic reducing pain in certain conditions. The drug was introduced in 1983 by the Warner-Lambert Company. Isoxicam is a chemical analog of piroxicam (Feldene) which has a pyridine ring in lieu of an isoxazole ring. In 1985 isoxicam was withdrawn from the French market, due to adverse effects, namely toxic epidermal necrolysis resulting in death. Although these serious side effects were observed only in France, the drug was withdrawn worldwide.
Chemical data
- Formula
- C14H13N3O5S
- Molecular weight
- 335.34 g/mol
- IUPAC name
- 4-hydroxy-2-methyl-N-(5-methyl-1,2-oxazol-3-yl)-1,1-dioxo-1lambda6,2-benzothiazine-3-carboxamide
- SMILES
- CC1=CC(=NO1)NC(=O)C2=C(C3=CC=CC=C3S(=O)(=O)N2C)O
- InChIKey
- YYUAYBYLJSNDCX-UHFFFAOYSA-N
- XLogP
- 3
- Polar surface area
- 121 Ų
- H-bond donors
- 2
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
Withdrawn- Max clinical phase
- Approved
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
131 papers- Isoxicam.Clinics in rheumatic diseases · 1984
- Evaluation of the safety of isoxicam.The American journal of medicine · 1985
- Pharmacokinetics of isoxicam in the elderly.The American journal of medicine · 1985
- Isoxicam vs ketoprofen in ankylosing spondylitis.British journal of clinical pharmacology · 1986
- The effect of administration of phenytoin on the pharmacokinetics of isoxicam.Biopharmaceutics & drug disposition · 1987
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 335.058
- Has use
- medication
Show 6 more facts
- chemical formula
- C₁₄H₁₃N₃O₅S
- canonical SMILES
- CC1=CC(=NO1)NC(=O)C2=C(C3=CC=CC=C3S(=O)(=O)N2C)O
- World Health Organisation international non-proprietary name
- isoxicam
- subject has role
- non-steroidal anti-inflammatory drug
- Commons category
- Isoxicam
- physically interacts with
- Prostaglandin-endoperoxide synthase 2
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Isoxicam is a nonsteroidal anti-inflammatory drug (NSAID) that was taken or applied to reduce inflammation and as an analgesic reducing pain in certain conditions. The drug was introduced in 1983 by the Warner-Lambert Company. Isoxicam is a chemical analog of piroxicam (Feldene) which has a pyridine ring in lieu of an isoxazole ring. In 1985 isoxicam was withdrawn from the French market, due to adverse effects, namely toxic epidermal necrolysis resulting in death. Although these serious side effects were observed only in France, the drug was withdrawn worldwide.
== References ==
Excerpted from Wikipedia’s “isoxicam” article, available under the CC BY-SA 4.0 licence.