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Identification
NameTenoxicam
Accession NumberDB00469  (APRD00011)
TypeSmall Molecule
GroupsApproved
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 Identifiers
  • RO 12-0068
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Mobiflex Tab 20mgtablet20 mgoralHoffmann La Roche Limited1991-12-312001-07-19Canada
Novo-tenoxicam Tab 20mgtablet20 mgoralNovopharm Limited1997-06-052005-08-10Canada
Nu-tenoxicamtablet20 mgoralNu Pharm IncNot applicableNot applicableCanada
Tenoxicam Tabletstablet20 mgoralAa Pharma Inc1997-02-21Not applicableCanada
Tenoxicam-20tablet20 mgoralPro Doc Limitee1998-11-242009-07-23Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
MobiflexRoche
OctiveranRafarm
OxicamACI
OxytelCoup
PalitenoxPharmathen
TenorixOrion
TenxilUnison
TilcotilMeda
TilflamDexa Medica
TilkoKoçak
TilnoxcamT. O. Chemicals
TiloxicanHexal
TobitilRanbaxy
TonoxUtopian
ToscacalmGenepharm
VelasorVocate
VienoksToprak
VoirVelka
XicotilAristopharma
ZibelantChrispa
ZikaralSanovel
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIZ1R9N0A399
CAS number59804-37-4
WeightAverage: 337.37
Monoisotopic: 337.019098194
Chemical FormulaC13H11N3O4S2
InChI KeyLZNWYQJJBLGYLT-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
Taxonomy
ClassificationNot classified
Pharmacology
IndicationFor the treatment of rheumatoid arthritis, osteoarthritis, backache, and pain.
PharmacodynamicsTenoxicam, an antiinflammatory agent with analgesic and antipyretic properties, is used to treat osteoarthritis and control acute pain.
Mechanism of actionThe 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.
Related Articles
AbsorptionOral absorption of tenoxicam is rapid and complete (absolute bioavailability 100%).
Volume of distributionNot Available
Protein binding99%
Metabolism

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

SubstrateEnzymesProduct
Tenoxicam
5'-HydroxytenoxicamDetails
Route of eliminationNot Available
Half life72 hours (range 59 to 74 hours)
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Tenoxicam Action PathwayDrug actionSMP00706
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot 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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point211 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
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area99.6 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity83.93 m3·mol-1ChemAxon
Polarizability31.96 Å3ChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesM01AC02
AHFS Codes
  • 28:08.04.92
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (57.1 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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 brain, and in pathological conditions, such as in cancer. PTGS2 is responsible for production of inflammatory prostaglandins. Up-regulation of PTGS2 is also associated with increased cell adhesion, p...
Gene Name:
PTGS2
Uniprot ID:
P35354
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 gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
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, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
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 ]
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Drug created on June 13, 2005 07:24 / Updated on May 12, 2016 15:59