Tenoxicam

Identification

Summary

Tenoxicam is an anti inflammatory analgesic used to treat mild to moderate pain as well as the signs and symptoms of rheumatoid arthritis and osteoarthritis.

Generic Name
Tenoxicam
DrugBank Accession Number
DB00469
Background

Tenoxicam, an antiinflammatory agent with analgesic and antipyretic properties, is used to treat osteoarthritis and control acute pain.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 337.37
Monoisotopic: 337.019098194
Chemical Formula
C13H11N3O4S2
Synonyms
  • Tenoxicam
  • Ténoxicam
  • Tenoxicamum
External IDs
  • RO 12-0068

Pharmacology

Indication

For the treatment of rheumatoid arthritis, osteoarthritis, backache, and pain.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofBackache••••••••••••
Management ofOsteoarthritis••••••••••••
Treatment ofPain••••••••••••
Management ofRheumatoid arthritis••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Tenoxicam, an antiinflammatory agent with analgesic and antipyretic properties, is used to treat osteoarthritis and control acute pain.

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.

TargetActionsOrganism
AProstaglandin G/H synthase 2
inhibitor
Humans
UProstaglandin G/H synthase 1
inhibitor
Humans
Absorption

Oral absorption of tenoxicam is rapid and complete (absolute bioavailability 100%).

Volume of distribution

Not Available

Protein binding

99%

Metabolism

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

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Route of elimination

Not Available

Half-life

72 hours (range 59 to 74 hours)

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Tenoxicam Action PathwayDrug action
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirTenoxicam may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbataceptThe metabolism of Tenoxicam can be increased when combined with Abatacept.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Tenoxicam is combined with Abciximab.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Tenoxicam.
AcamprosateThe excretion of Acamprosate can be decreased when combined with Tenoxicam.
Food Interactions
  • Take with food. Food may minimize stomach upset caused by tenoxicam.

Products

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International/Other Brands
Mobiflex (Roche) / Octiveran (Rafarm) / Oxicam (ACI) / Oxytel (Coup) / Palitenox (Pharmathen) / Tenorix (Orion) / Tenxil (Unison) / Tilcotil (Meda) / Tilflam (Dexa Medica) / Tilko (Koçak) / Tilnoxcam (T. O. Chemicals) / Tiloxican (Hexal) / Tobitil (Ranbaxy) / Tonox (Utopian) / Toscacalm (Genepharm) / Velasor (Vocate) / Vienoks (Toprak) / Voir (Velka) / Xicotil (Aristopharma) / Zibelant (Chrispa) / Zikaral (Sanovel)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Mobiflex Tab 20mgTablet20 mg / tabOralHoffmann La Roche1991-12-312001-07-19Canada flag
TenoxicamTablet20 mgOralAa Pharma Inc1997-02-21Not applicableCanada flag
TenoxicamTablet20 mgOralApotex CorporationNot applicableNot applicableCanada flag
Tenoxicam-20Tablet20 mgOralPro Doc Limitee1998-11-242009-07-23Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Novo-tenoxicam Tab 20mgTablet20 mgOralNovopharm Limited1997-06-052005-08-10Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
MAXCOTIL TEDAVI PAKETITenoxicam (20 mg) + Thiocolchicoside (4 mg)Powder, for solutionIntramuscularDeva Holding A.S.2020-08-142018-10-26Turkey flag
MİXOLEKS TEDAVİ PAKETİTenoxicam (20 mg) + Thiocolchicoside (4 mg)InjectionIntramuscularGENSENTA İLAÇ SANAYİ VE TİC. A.Ş.2011-06-30Not applicableTurkey flag

Categories

ATC Codes
M01AC02 — Tenoxicam
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids and derivatives
Alternative Parents
Thienothiazines / N-arylamides / Pyridines and derivatives / Organosulfonamides / Imidolactams / 1,2-thiazines / Vinylogous acids / Thiophenes / Heteroaromatic compounds / Secondary carboxylic acid amides
show 5 more
Substituents
Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Carbonyl group / Carboxamide group / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam / N-arylamide / Organic nitrogen compound
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monocarboxylic acid amide, pyridines, heteroaryl hydroxy compound, thienothiazine (CHEBI:32192)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
Z1R9N0A399
CAS number
59804-37-4
InChI Key
LZNWYQJJBLGYLT-UHFFFAOYSA-N
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)
IUPAC Name
4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1λ⁶-thieno[2,3-e][1,2]thiazine-3-carboxamide
SMILES
CN1C(C(=O)NC2=CC=CC=N2)=C(O)C2=C(C=CS2)S1(=O)=O

References

General References
Not Available
KEGG Drug
D01767
PubChem Compound
54677971
PubChem Substance
46507303
ChemSpider
10442339
BindingDB
92332
RxNav
37790
ChEBI
32192
ChEMBL
CHEMBL302795
ZINC
ZINC000100006429
Therapeutic Targets Database
DAP000736
PharmGKB
PA131890625
Wikipedia
Tenoxicam
MSDS
Download (57.1 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
4CompletedPreventionInjection Pain1
4CompletedSupportive CareMolar, Third / Pain1
4Unknown StatusTreatmentPostoperative pain1
2Unknown StatusTreatmentAnalgesia / Obstetrical1
1CompletedTreatmentArthrocentesis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, powder, lyophilized, for solutionIntramuscular; Intravenous20 mg
InjectionIntramuscular; Intravenous
Capsule20 mg
Granule, for suspensionOral
Injection, powder, for solutionIntramuscular
SuppositoryRectal
Capsule, liquid filledOral20 mg
Powder, for solutionIntramuscular
InjectionIntramuscular
TabletOral20 mg / tab
SuppositoryRectal20 mg
Injection, powder, for solutionIntramuscular; Intravenous20 mg
Tablet, film coatedOral
Capsule
TabletOral
Injection, powder, lyophilized, for solutionParenteral20 mg
Capsule, liquid filledOral21 mg
SolutionParenteral20 mg
Injection, solutionIntramuscular; Intravenous
Injection, powder, for solution
SolutionOral20.000 mg
InjectionIntramuscular; Intravenous20 mg/2ml
SolutionParenteral22 mg
Injection, powder, for solutionParenteral20 mg
InjectionIntramuscular; Intravenous20 mg
Tablet, delayed releaseOral20 mg
Tablet, film coatedOral20 mg
Tablet, coatedOral20 mg
TabletOral20 mg
Prices
Unit descriptionCostUnit
Apo-Tenoxicam 20 mg Tablet1.21USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)211 dec °CPhysProp
water solubility14.1 mg/LNot Available
logP1.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.257 mg/mLALOGPS
logP2.42ALOGPS
logP-0.12Chemaxon
logS-3.1ALOGPS
pKa (Strongest Acidic)2.21Chemaxon
pKa (Strongest Basic)4.26Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area99.6 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity83.93 m3·mol-1Chemaxon
Polarizability31.96 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9955
Blood Brain Barrier-0.9455
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.5536
P-glycoprotein inhibitor INon-inhibitor0.7976
P-glycoprotein inhibitor IINon-inhibitor0.8024
Renal organic cation transporterNon-inhibitor0.9191
CYP450 2C9 substrateSubstrate0.6922
CYP450 2D6 substrateNon-substrate0.8896
CYP450 3A4 substrateNon-substrate0.7105
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorInhibitor0.7661
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8966
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9057
Ames testNon AMES toxic0.8655
CarcinogenicityNon-carcinogens0.7271
BiodegradationNot ready biodegradable0.936
Rat acute toxicity3.4010 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9633
hERG inhibition (predictor II)Non-inhibitor0.8785
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-00di-4920000000-4540501176aeb1563469
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-4920000000-4540501176aeb1563469
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-cae7e427b6cac98216ae
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fk9-0950000000-b17850125b6a597032c1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00y0-2957000000-290337546b64f001a8c7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gb9-0791000000-98baf551af9c8cb4785f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0229-0359000000-3d048af235a9c051b822
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0301-6921000000-927cb93095551f21a099
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-174.4381279
predicted
DarkChem Lite v0.1.0
[M-H]-163.27448
predicted
DeepCCS 1.0 (2019)
[M+H]+173.8738279
predicted
DarkChem Lite v0.1.0
[M+H]+165.63249
predicted
DeepCCS 1.0 (2019)
[M+Na]+171.72563
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Kothekar V, Sahi S, Srinivasan M, Mohan A, Mishra J: Recognition of cyclooxygenase-2 (COX-2) active site by NSAIDs: a computer modelling study. Indian J Biochem Biophys. 2001 Feb-Apr;38(1-2):56-63. [Article]
  2. Yamada M, Niki H, Yamashita M, Mue S, Ohuchi K: Prostaglandin E2 production dependent upon cyclooxygenase-1 and cyclooxygenase-2 and its contradictory modulation by auranofin in rat peritoneal macrophages. J Pharmacol Exp Ther. 1997 May;281(2):1005-12. [Article]
  3. Ozgocmen S, Ardicoglu O, Erdogan H, Fadillioglu E, Gudul H: In vivo effect of celecoxib and tenoxicam on oxidant/ anti-oxidant status of patients with knee osteoarthritis. Ann Clin Lab Sci. 2005 Spring;35(2):137-43. [Article]
  4. Yilmaz H, Gurel S, Ozdemir O: The use and safety profile of non-steroidal antiinflammatory drugs among Turkish patients with osteoarthritis. Turk J Gastroenterol. 2005 Sep;16(3):138-42. [Article]
  5. Galvao RI, Diogenes JP, Maia GC, Filho EA, Vasconcelos SM, de Menezes DB, Cunha GM, Viana GS: Tenoxicam exerts a neuroprotective action after cerebral ischemia in rats. Neurochem Res. 2005 Jan;30(1):39-46. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Yamada M, Niki H, Yamashita M, Mue S, Ohuchi K: Prostaglandin E2 production dependent upon cyclooxygenase-1 and cyclooxygenase-2 and its contradictory modulation by auranofin in rat peritoneal macrophages. J Pharmacol Exp Ther. 1997 May;281(2):1005-12. [Article]
  2. Ozgocmen S, Ardicoglu O, Erdogan H, Fadillioglu E, Gudul H: In vivo effect of celecoxib and tenoxicam on oxidant/ anti-oxidant status of patients with knee osteoarthritis. Ann Clin Lab Sci. 2005 Spring;35(2):137-43. [Article]
  3. Lucio M, Ferreira H, Lima JL, Reis S: Interactions between oxicams and membrane bilayers: an explanation for their different COX selectivity. Med Chem. 2006 Sep;2(5):447-56. [Article]
  4. Lora M, Morisset S, Menard HA, Leduc R, de Brum-Fernandes AJ: Expression of recombinant human cyclooxygenase isoenzymes in transfected COS-7 cells in vitro and inhibition by tenoxicam, indomethacin and aspirin. Prostaglandins Leukot Essent Fatty Acids. 1997 May;56(5):361-7. [Article]
  5. Kothekar V, Sahi S, Srinivasan M, Mohan A, Mishra J: Recognition of cyclooxygenase-2 (COX-2) active site by NSAIDs: a computer modelling study. Indian J Biochem Biophys. 2001 Feb-Apr;38(1-2):56-63. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Vianna-Jorge R, Perini JA, Rondinelli E, Suarez-Kurtz G: CYP2C9 genotypes and the pharmacokinetics of tenoxicam in Brazilians. Clin Pharmacol Ther. 2004 Jul;76(1):18-26. doi: 10.1016/j.clpt.2004.03.002. [Article]
  2. Miners JO, Birkett DJ: Cytochrome P4502C9: an enzyme of major importance in human drug metabolism. Br J Clin Pharmacol. 1998 Jun;45(6):525-38. [Article]
  3. Rodrigues AD: Impact of CYP2C9 genotype on pharmacokinetics: are all cyclooxygenase inhibitors the same? Drug Metab Dispos. 2005 Nov;33(11):1567-75. Epub 2005 Aug 23. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Kobayashi Y, Ohshiro N, Tsuchiya A, Kohyama N, Ohbayashi M, Yamamoto T: Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. Drug Metab Dispos. 2004 May;32(5):479-83. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55