Identification

Name
Tenoxicam
Accession Number
DB00469  (APRD00011)
Type
Small Molecule
Groups
Approved
Description

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

Structure
Thumb
Synonyms
  • Tenoxicam
  • Ténoxicam
  • Tenoxicamum
External IDs
RO 12-0068
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mobiflex Tab 20mgTablet20 mgOralHoffmann La Roche1991-12-312001-07-19Canada
Tenoxicam TabletsTablet20 mgOralAa Pharma Inc1997-02-21Not applicableCanada
Tenoxicam-20Tablet20 mgOralPro Doc Limitee1998-11-242009-07-23Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Novo-tenoxicam Tab 20mgTablet20 mgOralNovopharm Limited1997-06-052005-08-10Canada
Nu-tenoxicamTablet20 mgOralNu Pharm IncNot applicableNot applicableCanada
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)
Categories
UNII
Z1R9N0A399
CAS number
59804-37-4
Weight
Average: 337.37
Monoisotopic: 337.019098194
Chemical Formula
C13H11N3O4S2
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

Pharmacology

Indication

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

Associated Conditions
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
Human
UProstaglandin G/H synthase 1
inhibitor
Human
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).

Route of elimination
Not Available
Half life

72 hours (range 59 to 74 hours)

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Tenoxicam Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of gastrointestinal bleeding can be increased when Tenoxicam is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of gastrointestinal bleeding can be increased when Tenoxicam is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of gastrointestinal bleeding can be increased when Tenoxicam is combined with 4-hydroxycoumarin.
AbacavirTenoxicam may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Tenoxicam is combined with Abciximab.
AcarboseTenoxicam may decrease the excretion rate of Acarbose which could result in a higher serum level.
AcebutololTenoxicam may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Tenoxicam is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Tenoxicam is combined with Acemetacin.
AcenocoumarolThe risk or severity of gastrointestinal bleeding can be increased when Tenoxicam is combined with Acenocoumarol.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D01767
PubChem Compound
54677971
PubChem Substance
46507303
ChemSpider
10442339
BindingDB
92332
ChEBI
32192
ChEMBL
CHEMBL302795
Therapeutic Targets Database
DAP000736
PharmGKB
PA131890625
Wikipedia
Tenoxicam
ATC Codes
M01AC02 — Tenoxicam
AHFS Codes
  • 28:08.04.92 — Other Nonsteroidal Antiimflammatory Agents
MSDS
Download (57.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Not Yet RecruitingTreatmentAnalgesia / Obstetrical1
4CompletedPreventionInjection Pain1
4Unknown StatusTreatmentPostoperative pain1
Not AvailableCompletedTreatmentKnee Osteoarthritis (Knee OA)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00di-4920000000-4540501176aeb1563469

Taxonomy

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 / Thienothiazine / N-arylamide / Ortho-thiazine / Pyridine / Imidolactam / Organosulfonic acid amide / Heteroaromatic compound / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monocarboxylic acid amide, pyridines, heteroaryl hydroxy compound, thienothiazine (CHEBI:32192)

Targets

Kind
Protein
Organism
Human
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. [PubMed:11563332]
  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. [PubMed:9152412]
  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. [PubMed:15943176]
  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. [PubMed:16245223]
  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. [PubMed:15756931]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
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. [PubMed:9152412]
  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. [PubMed:15943176]
  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. [PubMed:17017983]
  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. [PubMed:9175172]
  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. [PubMed:11563332]

Enzymes

Kind
Protein
Organism
Human
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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  2. Pelkonen O, Maenpaa J, Taavitsainen P, Rautio A, Raunio H: Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica. 1998 Dec;28(12):1203-53. [PubMed:9890159]
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Transporters

Kind
Protein
Organism
Human
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. [PubMed:15100168]

Drug created on June 13, 2005 07:24 / Updated on October 16, 2018 05:48