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Identification
Name Lornoxicam
Accession Number DB06725
Type small molecule
Groups approved
Description

Lornoxicam (chlortenoxicam) is a new nonsteroidal anti-inflammatory drug (NSAID) of the oxicam class with analgesic, anti-inflammatory and antipyretic properties. Lornoxicam differs from other oxicam compounds in its potent inhibition of prostaglandin biosynthesis, a property that explains the particularly pronounced efficacy of the drug. Lornoxicam is approved for use in Japan.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Acabel
chlortenoxicam
CLTX
Lorcam
Lorcam (TN)
Lornoxicamum
Lornoxicamum [inn-latin]
Safem
Taigalor
Telos
XEFO
Xefocam
First Prev Next Last
Salts Not Available
Brand names
Name Company
Lorcam Taisho Pharmaceutical Co.
Xafon Nycomed
Brand mixtures Not Available
Categories
  • Analgesics
  • Nonsteroidal Anti-inflammatory Agents (NSAIAs)
CAS number 70374-39-9
Weight Average: 371.819
Monoisotopic: 370.98012491
Chemical Formula C13H10ClN3O4S2
InChI Key InChIKey=OXROWJKCGCOJDO-JLHYYAGUSA-N
InChI
InChI=1S/C13H10ClN3O4S2/c1-17-10(13(19)16-9-4-2-3-5-15-9)11(18)12-7(23(17,20)21)6-8(14)22-12/h2-6,19H,1H3,(H,15,16)/b13-10+
Plain Text
IUPAC Name
(3E)-6-chloro-3-{hydroxy[(pyridin-2-yl)amino]methylidene}-2-methyl-2H,3H,4H-1$l^{6},5,2-thieno[2,3-e][1$l^{6},2]thiazine-1,1,4-trione
SMILES
CN1\C(=C(\O)NC2=CC=CC=N2)C(=O)C2=C(C=C(Cl)S2)S1(=O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For the treatment of acute mild to moderate pain, as well as pain and inflammation of the joints caused by certain types of rheumatic diseases.
Pharmacodynamics Lornoxicam is a non-steroidal anti-inflammatory drug (NSAID) that belongs to the oxicam class. As with other NSAIDS, lornoxicam is a potent inhibitor of the cyclooxgenase enzymes, which are responsible for catalyzing the formation of prostaglandins (act as messenger molecules in the process of inflammation) and thromboxane from arachidonic acid. Unlike some NSAIDS, lornoxicam's inhibition of cyclooxygenase does not lead to an increase in leukotriene formation, meaning that arachidonic acid is not moved to the 5-lipoxygenase cascade, resulting in the minimization of the risk of adverse events.
Mechanism of action Like other NSAIDS, lornoxicam's anti-inflammatory and analgesic activity is related to its inhibitory action on prostaglandin and thromboxane synthesis through the inhibition of both COX-1 and COX-2. This leads to the reduction of inflammation, pain, fever, and swelling, which are mediated by prostaglandins. However, the exact mechanism of lornoxicam, like that of the other NSAIDs, has not been fully determined.
Absorption Lornoxicam is absorbed rapidly and almost completely from the GI tract (90-100%).
Volume of distribution Not Available
Protein binding Lornoxicam is 99% bound to plasma proteins (almost exlusively to serum albumin).
Metabolism
Lornoxicam is metabolized completely by cyp 2C9 with the principal metabolite being 5'-hydroxy-lornoxicam and only negligible amounts of intact lornoxicam are excreted unchanged in the urine. Approximately 2/3 of the drug is eliminated via the liver and 1/3 via the kidneys in the active form.

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Substrate Enzymes Product
Lornoxicam
5'-Hydroxylornoxicam Details
Lornoxicam
    		5'-Hydroxy-lornoxicam Details
    Lornoxicam
      		Lornoxicam Details
      Route of elimination Not Available
      Half life 3-5 hours
      Clearance Not Available
      Toxicity Not Available
      Affected organisms
      • Humans and other mammals
      Pathways Not Available
      Pharmacoeconomics
      Manufacturers Not Available
      Packagers Not Available
      Dosage forms
      Form Route Strength
      Injection Intravenous 4 mg/ml
      Tablet Oral 4 mg
      Tablet Oral 8 mg
      Prices Not Available
      Patents Not Available
      Properties
      State solid
      Experimental Properties
      Property Value Source
      logP 2.62 BIOBYTE STARLIST (2009)
      Predicted Properties
      Property Value Source
      water solubility 4.61e-02 g/l ALOGPS
      logP 2.53 ALOGPS
      logP 1.99 ChemAxon
      logS -3.9 ALOGPS
      pKa (strongest acidic) 6.88 ChemAxon
      pKa (strongest basic) 4.78 ChemAxon
      physiological charge -1 ChemAxon
      hydrogen acceptor count 6 ChemAxon
      hydrogen donor count 2 ChemAxon
      polar surface area 99.6 ChemAxon
      rotatable bond count 2 ChemAxon
      refractivity 97.02 ChemAxon
      polarizability 33.77 ChemAxon
      References
      Synthesis Reference Not Available
      General Reference
      1. Balfour JA, Fitton A, Barradell LB: Lornoxicam. A review of its pharmacology and therapeutic potential in the management of painful and inflammatory conditions. Drugs. 1996 Apr;51(4):639-57. Pubmed
      2. Vane JR: Introduction: mechanism of action of NSAIDs. Br J Rheumatol. 1996 Apr;35 Suppl 1:1-3. Pubmed
      3. Radhofer-Welte S, Rabasseda X: Lornoxicam, a new potent NSAID with an improved tolerability profile. Drugs Today (Barc). 2000 Jan;36(1):55-76. Pubmed
      4. Skjodt NM, Davies NM: Clinical pharmacokinetics of lornoxicam. A short half-life oxicam. Clin Pharmacokinet. 1998 Jun;34(6):421-8. Pubmed
      5. Olkkola KT, Brunetto AV, Mattila MJ: Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents. Clin Pharmacokinet. 1994 Feb;26(2):107-20. Pubmed
      6. Hitzenberger G, Radhofer-Welte S, Takacs F, Rosenow D: Pharmacokinetics of lornoxicam in man. Postgrad Med J. 1990;66 Suppl 4:S22-7. Pubmed
      7. Pruss TP, Stroissnig H, Radhofer-Welte S, Wendtlandt W, Mehdi N, Takacs F, Fellier H: Overview of the pharmacological properties, pharmacokinetics and animal safety assessment of lornoxicam. Postgrad Med J. 1990;66 Suppl 4:S18-21. Pubmed
      8. Bonnabry P, Leemann T, Dayer P: Role of human liver microsomal CYP2C9 in the biotransformation of lornoxicam. Eur J Clin Pharmacol. 1996;49(4):305-8. Pubmed
      External Links
      Resource Link
      KEGG Drug D01866 Link_out
      PubChem Compound 5282204 Link_out
      PubChem Substance 99443271 Link_out
      ChemSpider 4445392 Link_out
      PharmGKB PA165958395 Link_out
      Wikipedia http://en.wikipedia.org/wiki/Lornoxicam Link_out
      ATC Codes
      • M01AC05
      AHFS Codes Not Available
      PDB Entries Not Available
      FDA label Not Available
      MSDS Not Available
      Interactions
      Drug Interactions Not Available
      Food Interactions Not Available
      Targets

      1. Prostaglandin G/H synthase 1

      Pharmacological action: yes
      Actions: inhibitor

      May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells

      Organism class: human
      UniProt ID: P23219 Link_out
      Gene: PTGS1 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Renner RM, Jensen JT, Nichols MD, Edelman AB: Pain control in first-trimester surgical abortion: a systematic review of randomized controlled trials. Contraception. 2010 May;81(5):372-88. Epub 2010 Jan 27. Pubmed
      2. Berg J, Fellier H, Christoph T, Grarup J, Stimmeder D: The analgesic NSAID lornoxicam inhibits cyclooxygenase (COX)-1/-2, inducible nitric oxide synthase (iNOS), and the formation of interleukin (IL)-6 in vitro. Inflamm Res. 1999 Jul;48(7):369-79. Pubmed
      3. Rose P, Steinhauser C: Comparison of Lornoxicam and Rofecoxib in Patients with Activated Osteoarthritis (COLOR Study). Clin Drug Investig. 2004;24(4):227-36. Pubmed
      4. Bianchi M, Panerai AE: Effects of lornoxicam, piroxicam, and meloxicam in a model of thermal hindpaw hyperalgesia induced by formalin injection in rat tail. Pharmacol Res. 2002 Feb;45(2):101-5. Pubmed

      2. Prostaglandin G/H synthase 2

      Pharmacological action: yes
      Actions: inhibitor

      May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity

      Organism class: human
      UniProt ID: P35354 Link_out
      Gene: PTGS2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Renner RM, Jensen JT, Nichols MD, Edelman AB: Pain control in first-trimester surgical abortion: a systematic review of randomized controlled trials. Contraception. 2010 May;81(5):372-88. Epub 2010 Jan 27. Pubmed
      2. Berg J, Fellier H, Christoph T, Grarup J, Stimmeder D: The analgesic NSAID lornoxicam inhibits cyclooxygenase (COX)-1/-2, inducible nitric oxide synthase (iNOS), and the formation of interleukin (IL)-6 in vitro. Inflamm Res. 1999 Jul;48(7):369-79. Pubmed
      3. Rose P, Steinhauser C: Comparison of Lornoxicam and Rofecoxib in Patients with Activated Osteoarthritis (COLOR Study). Clin Drug Investig. 2004;24(4):227-36. Pubmed
      4. Bianchi M, Panerai AE: Effects of lornoxicam, piroxicam, and meloxicam in a model of thermal hindpaw hyperalgesia induced by formalin injection in rat tail. Pharmacol Res. 2002 Feb;45(2):101-5. Pubmed
      Enzymes

      1. Cytochrome P450 2C9

      Actions: substrate, inhibitor

      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, phenytoin, tolbutamide and losartan

      UniProt ID: P11712 Link_out
      Gene: CYP2C9
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      SNPs: SNPJam Report Link_out

      References:
      1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
      2. 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. Pubmed
      3. Martinez C, Blanco G, Garcia-Martin E, Agundez JA: [Clinical pharmacogenomics for CYP2C8 and CYP2C9: general concepts and application to the use of NSAIDs] Farm Hosp. 2006 Jul-Aug;30(4):240-8. Pubmed
      4. Zhang Y, Zhong D, Si D, Guo Y, Chen X, Zhou H: Lornoxicam pharmacokinetics in relation to cytochrome P450 2C9 genotype. Br J Clin Pharmacol. 2005 Jan;59(1):14-7. Pubmed
      5. Kohl C, Steinkellner M: Prediction of pharmacokinetic drug/drug interactions from In vitro data: interactions of the nonsteroidal anti-inflammatory drug lornoxicam with oral anticoagulants. Drug Metab Dispos. 2000 Feb;28(2):161-8. Pubmed
      6. Bonnabry P, Leemann T, Dayer P: Role of human liver microsomal CYP2C9 in the biotransformation of lornoxicam. Eur J Clin Pharmacol. 1996;49(4):305-8. Pubmed
      7. 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
      8. 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. Epub 2009 Nov 24. Pubmed
      Comments
      Drug created on August 18, 2010 12:12 / Updated on February 08, 2013 16:24