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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
Structure of TENOXICAM

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)

HIDE SMILES / InChI

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

Description
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).

Originator

Curator's Comment: # Hoffmann La Roche

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
PubMed

PubMed

TitleDatePubMed
Acute hepatitis caused by tenoxicam.
1994 Nov
Intravenous tenoxicam for analgesia following laparoscopic cholecystectomy.
1998 Feb
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Prolonged cholestasis and ductopenia associated with tenoxicam.
2003 Jul
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Non-steroidal anti-inflammatory drug-related hepatic damage in France and Spain: analysis from national spontaneous reporting systems.
2006 Aug
Indirect role of beta2-adrenergic receptors in the mechanism of anti-inflammatory action of NSAIDS.
2008 Dec
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
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 admin
on Wed Jul 05 22:37:59 UTC 2023
Edited
by admin
on Wed Jul 05 22:37:59 UTC 2023
Record UNII
Z1R9N0A399
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TENOXICAM
EP   INN   JAN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
TENOXICAM [EP MONOGRAPH]
Common Name English
TENOXICAM [USAN]
Common Name English
NSC-758397
Code English
RO 12-0068
Code English
Tenoxicam [WHO-DD]
Common Name English
RO-12-0068/000
Code English
TENOXICAM [JAN]
Common Name English
TENOXICAM [MART.]
Common Name English
RO 12-0068/000
Code English
TILCOTIL
Brand Name English
RO-120068000
Code English
TENOXICAM [MI]
Common Name English
tenoxicam [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C257
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
WHO-VATC QM01AC02
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
WHO-ATC M01AC02
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
Code System Code Type Description
MERCK INDEX
M10561
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY Merck Index
NSC
758397
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY
FDA UNII
Z1R9N0A399
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY
WIKIPEDIA
TENOXICAM
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY
DRUG BANK
DB00469
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID8045486
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY
EVMPD
SUB10900MIG
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY
CHEBI
32192
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY
CAS
59804-37-4
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY
ChEMBL
CHEMBL302795
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY
PUBCHEM
54677971
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY
SMS_ID
100000082679
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY
NCI_THESAURUS
C73097
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY
MESH
C032801
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY
USAN
Z-11
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY
RXCUI
37790
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY RxNorm
INN
4915
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY
DRUG CENTRAL
2595
Created by admin on Wed Jul 05 22:37:59 UTC 2023 , Edited by admin on Wed Jul 05 22:37:59 UTC 2023
PRIMARY
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY