Tenoxicam

HCID 54677971CAS 59804-37-4

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

tenoxicam59804-37-4MobiflexTilcotilTenoxicamumRo 12-0068Ro 12-0068/000DTXSID8045486Ro-12-0068NSC-758397CHEBI:32192Z1R9N0A399
Weitere Namen anzeigen
Tenoxicam CRSLornoxicam Impurity 44SoralLimanDo1menDolmenTilatil
4-Hydroxy-2-methyl-N-2-pyridyl-2H-thieno(2,3-e)-1,2-thiazine-3-carboxamide 1,1-dioxideRo-120068000DTXCID6025486RO-12-0068/000RefChem:891355M01AC024-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1??-thieno(2,3-e)(1,2)thiazine-3-carboxamideAlganex

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

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
LogP1.9
Human DrugsPharmaceuticals
Collision Cross Section · 3 Einträge

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℃)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

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

Hazard Classes and CategoriesAcute Tox. 3 (97.8%)

Toxikologische Informationen

Drug Induced Liver Injury · 5 Einträge

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

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

M01AC02

M - Musculo-skeletal system

QM - Musculo-skeletal system

Protein Binding99%
PharmacodynamicsTenoxicam, an antiinflammatory agent with analgesic and antipyretic properties, is used to treat osteoarthritis and control acute pain.
Mechanism of Action · 1 Eintrag

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.

Biological Half-Life72 hours (range 59 to 74 hours)
Metabolism/Metabolites · 2 Einträge

Tenoxicam is metabolized in the liver to several pharmacologically inactive metabolites (mainly 5'-hydroxy-tenoxicam).

Tenoxicam has known human metabolites that include 5'-Hydroxytenoxicam.

Verwendung und Herstellung

Use ClassificationPharmaceuticals
Anwendungen · 2 Einträge

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

Anbieter50 Anbieter

北京华美互利生物化工010-56205725 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
济南百隆化学有限公司[email protected] · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
Ergänzende Hinweise · 1 Eintrag

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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