Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C13H11N3O4S2 |
| Molecular Weight | 337.374 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1C(C(=O)NC2=CC=CC=N2)=C(O)C3=C(C=CS3)S1(=O)=O
InChI
InChIKey=LZNWYQJJBLGYLT-UHFFFAOYSA-N
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)
| Molecular Formula | C13H11N3O4S2 |
| Molecular Weight | 337.374 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: https://www.drugbank.ca/drugs/DB00469Curator's Comment: description was created based on several sources, including
https://www.drugs.com/international/tenoxicam.html | https://www.ncbi.nlm.nih.gov/pubmed/24466249 | https://www.ncbi.nlm.nih.gov/pubmed/9152412
Sources: https://www.drugbank.ca/drugs/DB00469
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/international/tenoxicam.html | https://www.ncbi.nlm.nih.gov/pubmed/24466249 | https://www.ncbi.nlm.nih.gov/pubmed/9152412
Tenoxicam (Mobiflex), an anti-inflammatory agent with analgesic and antipyretic properties, is used to treat osteoarthritis and control acute pain. The anti-inflammatory effects of tenoxicam may result from the inhibition of the enzyme cyclooxygenase 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. Taking tenoxicam with other drugs can increase the chance of side effects or alter the therapeutic effect of tenoxicam or the other drug, depending on the combination. Drug types the tenoxicam may interact with include: other analgesic NSAIDs, salicylates such as aspirin, antacids, anticoagulants, cardiac glycosides, ciclosporin, quinolone antibiotics, lithium therapy, diuretics and anti-hypertensives, methotrexate, oral anti-diabetics, cholestyramine, dextromethorphan, mifepristone, corticosteroids, anti-platelet agents and selective serotonin reuptake inhibitors (SSRIs), tacrolimus, zidovudine, and gold/penicillamine. Tenoxicam is available as a prescription-only drug in the United Kingdom and other countries, but not in the US. Outside of the United Kingdom, tenoxicam is also marketed under brand names including Tilatil, Tilcitin, and Alganex. Tenoxicam belongs to the class of NSAIDs known as oxicams. It is used to relieve inflammation, swelling, stiffness, and pain associated with rheumatoid arthritis, osteoarthritis, ankylosing spondylitis (a type of arthritis involving the spine), tendinitis (inflammation of a tendon), bursitis (inflammation of a bursa, a fluid-filled sac located around joints and near the bones), and peri-arthritis of the shoulders or hips (inflammation of tissues surrounding these joints).
CNS Activity
Originator
Sources: https://google.com/patents/DE2537070A1
Curator's Comment: # Hoffmann La Roche
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9152412 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Tenoxicam Approved UseUnknown |
|||
| Primary | Tenoxicam Approved UseUnknown |
|||
| Primary | Tenoxicam Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.76 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2788089/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOXICAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
13.63 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2788089/ |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
TENOXICAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
242.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2788089/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOXICAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
262.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2788089/ |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
TENOXICAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
134 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3497039/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOXICAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
260 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3497039/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOXICAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
460 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3497039/ |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOXICAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
66.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2788089/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOXICAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
74.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2788089/ |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
TENOXICAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
72.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3497039/ |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOXICAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
80.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3497039/ |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOXICAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
75.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3497039/ |
40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered: |
TENOXICAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2053921/ |
20 mg 1 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
TENOXICAM plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
40 mg 1 times / day multiple, intravenous Higher than recommended Dose: 40 mg, 1 times / day Route: intravenous Route: multiple Dose: 40 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
|
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Nausea, Vomiting... Other AEs: Dyspepsia... AEs leading to discontinuation/dose reduction: Nausea (12%) Other AEs:Vomiting (3.4%) Dyspepsia (12%) Sources: |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Gastrointestinal disorder, Blood in stool... AEs leading to discontinuation/dose reduction: Gastrointestinal disorder (4%) Sources: Blood in stool (0.7%) Gastric ulcer (0.7%) Dizziness (grade 3, 1.4%) Rash (0.7%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Dyspepsia | 12% | 20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Nausea | 12% Disc. AE |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Vomiting | 3.4% Disc. AE |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Blood in stool | 0.7% Disc. AE |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Gastric ulcer | 0.7% Disc. AE |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Rash | 0.7% Disc. AE |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Gastrointestinal disorder | 4% Disc. AE |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Dizziness | grade 3, 1.4% Disc. AE |
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| inconclusive [IC50 2.5119 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >10 uM] | ||||
| no [IC50 >133 uM] | ||||
| no [IC50 >133 uM] | ||||
| no [IC50 >133 uM] | ||||
| no [IC50 >133 uM] | ||||
Page: 16.0 |
no [IC50 >50 uM] | |||
Page: 53.0 |
no | |||
Page: 374.0 |
no | |||
Page: 428.0 |
no | |||
Page: 29.0 |
no | |||
Page: 55.0 |
no | |||
| yes [Inhibition 10 uM] | ||||
| yes [Inhibition 10 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 419 | 420 |
no | |||
| yes | yes (pharmacogenomic study) Comment: No significant differences were observed in Cmin, Cmax, or AUC between CYP2C9*1/*2 and either CYP2C9*1/*1 or CYP2C9*1/*3 individuals. |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Indirect role of beta2-adrenergic receptors in the mechanism of anti-inflammatory action of NSAIDS. | 2008-12 |
|
| Non-steroidal anti-inflammatory drug-related hepatic damage in France and Spain: analysis from national spontaneous reporting systems. | 2006-08 |
|
| Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005-06 |
|
| Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. | 2004-05 |
|
| Prolonged cholestasis and ductopenia associated with tenoxicam. | 2003-07 |
|
| Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001-11 |
|
| Eotaxin expression and eosinophil infiltrate in the liver of patients with drug-induced liver disease. | 2001-04 |
|
| Intravenous tenoxicam for analgesia following laparoscopic cholecystectomy. | 1998-02 |
|
| Acute hepatitis caused by tenoxicam. | 1994-11 |
|
| A comparison of tenoxicam and piroxicam in the treatment of rheumatoid arthritis. | 1992-04 |
|
| Clinical efficacy and tolerability of tenoxicam in African patients with osteoarthritis, rheumatoid arthritis, tendinitis and/or bursitis: an open study. | 1991 |
Patents
Sample Use Guides
Adult: PO- 20 mg/day as single dose for 7 days in acute disorders, up to 14 days in severe cases. Max: 40 mg/day (short term use).
IV/IM- 20 mg/day as single dose for 1-2 days.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9152412
The peritoneal cells were suspended in Eagle’s minimal essential medium containing 10% (v/v) calf serum, penicillin G potassium (18 mg/ml) and streptomycin sulfate (50 mg/ml) at a density of 1.5 x 106 cells per milliliter. One milliliter of the cell suspension was poured into each well of a 12-well plastic tissue culture plate (Coster Co.), and the plates were incubated for 2 h at 37°C. The wells were then washed three times with medium to remove nonadherent cells. The adherent cells were incubated for 4 h at 37°C in 1 ml of medium containing TENOXICAM. After three washes to remove free aspirin, the cells were further incubated for 4 h at 37°C in 1 ml of medium containing TPA (Sigma Chemical Co.) (16.2 nM) in the absence of arachidonic acid. After incubation, the conditioned medium was collected to determine the PGE2 concentration.
| Substance Class |
Chemical
Created
by
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on
Edited
Mon Mar 31 17:46:26 GMT 2025
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| Record UNII |
Z1R9N0A399
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C257
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WHO-VATC |
QM01AC02
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WHO-ATC |
M01AC02
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m10561
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758397
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Z1R9N0A399
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TENOXICAM
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DB00469
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DTXSID8045486
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SUB10900MIG
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32192
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59804-37-4
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CHEMBL302795
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54677971
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100000082679
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C73097
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C032801
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Z-11
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37790
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4915
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2595
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
correction factors: for the calculation of content, multiply the peak areas of the following impurities by the corresponding correction factor: impurity A = 0.2
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |