Grundinformationen
- Standard-SMILES
CN1C(C(=O)Nc2ccccn2)=C(O)c2sccc2S1(=O)=O- InChIKey
LZNWYQJJBLGYLT-UHFFFAOYSA-N- Summenformel
- C13H11N3O4S2
- Durchschnittliche Molmasse
- 337,4 g/mol
- Monoisotopische Masse
- 337,01909783
Überblick
Tenoxicam is a thienothiazine-derived monocarboxylic acid amide obtained by formal condensation of the carboxy group of 4-hydroxy-2-methylthieno[2,3-e][1,2]thiazine-3-carboxylic acid 1,1-dioxide with the amino group of 2-aminopyridine. Used for the treatment of pain and inflammation in osteoarthritis and rheumatoid arthritis. It is also indicated for short term treatment of acute musculoskeletal disorders including strains, sprains and other soft-tissue injuries. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antipyretic and an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor. It is a member of pyridines, a monocarboxylic acid amide, a thienothiazine and a heteroaryl hydroxy compound.
Namen und Bezeichner
- Bevorzugter Name
- Tenoxicam
- IUPAC
- 4-hydroxy-2-methyl-1,1-dioxo-N-pyridin-2-ylthieno[2,3-e]thiazine-3-carboxamide
- Englischer Name
- Tenoxicam
- Summenformel
- C13H11N3O4S2
- Molmasse
- 337.37
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
59804-37-4- PubChem CID
- 54677971
- DTXSID
DTXSID8045486- ChEMBL
CHEMBL302795、CHEMBL3188633- ChEBI
CHEBI:32192- UNII
- Z1R9N0A399
- EC Number
- 620-500-8
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,1
- Polarare Oberfläche (TPSA)
- 136 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 22
- Formalladung
- 0
- Komplexität
- 599
Experimentelle und physikochemische Eigenschaften
Collision Cross Section
169.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
170.4 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
175.02 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 209 · 209-2130C (dec)
- Dichte
- 1.4737 · 1.4737 (rough estimate)
- Brechungsindex
- 1.639 · 1.6390 (estimate)
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Practically insoluble in water, sparingly soluble in methylene chloride, very slightly soluble in anhydrous ethanol. It dissolves in solutions of acids and alkalis.
- pka
- 1 · pKa1 5.3, pKa2 1.1(at 25℃)
- Aggregatzustand
- Solid
- Farbe
- White to Yellow to Green
- Wasserlöslichkeit
- 61.9 mg/L · 61.9mg/L(32 ºC)
- Major Application
- pharmaceuticalpharmaceutical small molecule
- InChI
- InChI=1S/C13H11N3O4S2/c1-16-10(13(18)15-9-4-2-3-6-14-9)11(17)12-8(5-7-21-12)22(16,19)20/h2-7,17H,1H3,(H,14,15,18)
- InChIKey
- LZNWYQJJBLGYLT-UHFFFAOYSA-N
- SMILES
- S1(=O)(=O)C2C=CSC=2C(O)=C(C(NC2=NC=CC=C2)=O)N1C
- CAS Datenbank
- 59804 · 59804-37-4
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 2.2% (1 of 46) of reports.
Danger
H301 (97.8%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Toxikologische Informationen
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
TENOXICAM
DILI Positive
Oral
DOI:10.1016/j.drudis.2019.09.022
Sicherheitsdaten
- wgk
- 2
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 2934.99.3000
- RTECS-Nr.
- XJ9095060
- risk_code
- 23/24/25-36/37/38
- hazard_code
- T,Xi
- safety_code
- 36/37/39-45-36-26-36/37
- hazard_class
- 6.1
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 Oral
Chemie und Industrie
Pharmakologische Informationen
ATC Code
M01AC02
M - Musculo-skeletal system
QM - Musculo-skeletal system
Mechanism of Action
The antiinflammatory effects of tenoxicam may result from the inhibition of the enzyme cycooxygenase and the subsequent peripheral inhibition of prostaglandin synthesis. As prostaglandins sensitize pain receptors, their inhibition accounts for the peripheral analgesic effects of tenoxicam. Antipyresis may occur by central action on the hypothalamus, resulting in peripheral dilation, increased cutaneous blood flow, and subsequent heat loss.
Metabolism/Metabolites
Tenoxicam is metabolized in the liver to several pharmacologically inactive metabolites (mainly 5'-hydroxy-tenoxicam).
Tenoxicam has known human metabolites that include 5'-Hydroxytenoxicam.
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.
Compounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes.
Verwendung und Herstellung
Anwendungen
BeschreibungTenoxicam is a non-steroidal antiinflammatory agent with a profile similar to related piroxicam and now withdrawn isoxicam (55). It is useful in the treatment of rheumatoid arthritis, osteoarthritis and related disorders.
VerwendenTenoxicam has been used: as a non-steroidal anti-inflammatory agent (NSAID) to study its effects on root gravitropism in Arabidopsis thaliana as a standard in microanalysis of NSAIDs by spectrophotometry to test its effect on surface potential andmembrane fluidity modification in phosphoglyceride monolayers
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: Tenoxicam is a thienothiazine-derived monocarboxylic acid amide obtained by formal condensation of the carboxy group of 4-hydroxy-2-methylthieno[2,3-e][1,2]thiazine-3-carboxylic acid 1,1-dioxide with the amino group of 2-aminopyridine. Used for the treatment of pain and inflammation in osteoarthritis and rheumatoid arthritis. It is also indicated for short term treatment of acute musculoskeletal disorders including strains, sprains and other soft-tissue injuries. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antipyretic and an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor. It is a heteroaryl hydroxy compound, a monocarboxylic acid amide, a member of pyridines and a thienothiazine.
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