Isoxicam
Grundinformationen
- CAS
34552-84-6- Standard-SMILES
Cc1cc(NC(=O)C2=C(O)c3ccccc3S(=O)(=O)N2C)no1- InChIKey
YYUAYBYLJSNDCX-UHFFFAOYSA-N- Summenformel
- C14H13N3O5S
- Durchschnittliche Molmasse
- 335,34 g/mol
- Monoisotopische Masse
- 335,05759152
Überblick
Isoxicam is 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 A non-steroidal anti-inflammatory drug, it was withdrawn from the market in the 1980s following its association with cases of Stevens-Johnson syndrome. It has a role as a non-steroidal anti-inflammatory drug and an antirheumatic drug. It is a monocarboxylic acid amide, a benzothiazine and a member of isoxazoles.
Namen und Bezeichner
- Bevorzugter Name
- Isoxicam
- IUPAC
- 4-hydroxy-2-methyl-N-(5-methyl-1,2-oxazol-3-yl)-1,1-dioxo-1λ6,2-benzothiazine-3-carboxamide
- Lokaler Name
- Isoxicam
- Englischer Name
- ISOXICAM
- Summenformel
- C14H13N3O5S
- Molmasse
- 335.34
Namen und Synonyme
isoxicam34552-84-6MaxicamIsoxicamumIsoxicamoW 8495DTXSID0045462BRN 0577221NSC-7584368XU734C4NGCHEBI:761632H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-(5-methyl-3-isoxazolyl)-, 1,1-dioxide
Weitere Namen anzeigen
PacylVectren)-,1,1-dioxidepacyl(antiinflammatory)[Gly8]-GLP-1(7-37) acetate
W-8495DTXCID80254624-Hydroxy-2-methyl-N-(5-methyl-3-isoxazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide4-hydroxy-2-methyl-N-(5-methyl-1,2-oxazol-3-yl)-1,1-dioxo-1lambda6,2-benzothiazine-3-carboxamideRefChem:792457252-084-54-hydroxy-2-methyl-N-(5-methyl-1,2-oxazol-3-yl)-1,1-dioxo-2H-1lambda6,2-benzothiazine-3-carboxamideEINECS 252-084-5
Datenbank-Bezeichner
- CAS
34552-84-6- PubChem CID
- 54677972
- DTXSID
DTXSID0045462- ChEMBL
CHEMBL53292- ChEBI
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3
- Polarare Oberfläche (TPSA)
- 121 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 23
- Formalladung
- 0
- Komplexität
- 627
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
LogP2.83
Solubility33.9 [ug/mL] (The mean of the results at pH 7.4)
Human DrugsPharmaceuticals
Collision Cross Section
181.65 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
170.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 265 · 265-271℃
- Dichte
- 1.588 · 1.588
- storage temp.
- -20 °C · -20°C Freezer
- Löslichkeit
- Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
- Aggregatzustand
- Solid
- pka
- 4.5 · 4.50±1.00(Predicted)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Gefahrenhinweise
Other Safety InformationIMAP assessments - 2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-(5-methyl-3-isoxazolyl)-, 1,1-dioxide: Environment tier I assessment
Toxikologische Informationen
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
isoxicam
DILI Negative
DOI:10.1016/j.drudis.2019.09.022
Sicherheitsdaten
- wgk
- 2
- RTECS-Nr.
- DL0703000
- Toxizität
- LD50 in rats (mg/kg): >5000 orally (Whitehouse)
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Verwendung und Herstellung
Use ClassificationPharmaceuticals
Anwendungen
BeschreibungIsoxicam 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.
VerwendenIsoxicam is used for the same indications as piroxicam. Synonyms for isoxicam are floxicam and maxicam.
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