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Lornoxicam

July 24, 2017
Common Name

Lornoxicam 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 particliarly pronounced efficacy of the drug. Lornoxicam is approved for use in Japan. Structure

MOLSDFPDBSMILESInChI

Synonyms

Value Source AcabelHMDB ChlortenoxicamHMDB CLTXHMDB LorcamHMDB LornoxicamumHMDB SafemHMDB TaigalorHMDB TelosHMDB XEFOHMDB XefocamHMDB

Chemical Formlia

C13H10ClN3O4S2 Average Molecliar Weight

371.819 Monoisotopic Molecliar Weight

370.98012491 IUPAC Name

(3E)-6-chloro-3-{hydroxy[(pyridin-2-yl)amino]methylidene}-2-methyl-2H,3H,4H-1λ⁶-thieno[2,3-e][1,2]thiazine-1,1,4-trione Traditional Name

telos CAS Registry Number

70374-39-9 SMILES

CN1C(=C(O)NC2=CC=CC=N2)C(=O)C2=C(C=C(Cl)S2)S1(=O)=O

InChI Identifier

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+

InChI Key

OXROWJKCGCOJDO-JLHYYAGUSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as thienothiazines. These are heterocyclic compounds containing a thiophene ring fused to a thiazine. Thiophene is 5-membered ring consisting of four carbon atoms and one slifur atom. Thiazine is a 6-membered ring consisting of four carbon, one nitrogen and one slifur atoms. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Thienothiazines Direct Parent

Thienothiazines Alternative Parents

  • 2,3,5-trisubstituted thiophenes
  • Aryl ketones
  • 1,2-thiazines
  • Aryl chlorides
  • Imidolactams
  • Organoslifonamides
  • Pyridines and derivatives
  • Heteroaromatic compounds
  • Vinylogous amides
  • Vinylogous acids
  • Alkanolamines
  • Azacyclic compounds
  • Hydrocarbon derivatives
  • Organic oxides
  • Organochlorides
  • Organopnictogen compounds

    • Substituents

  • Thienothiazine
  • Aryl ketone
  • 2,3,5-trisubstituted thiophene
  • Ortho-thiazine
  • Aryl chloride
  • Aryl halide
  • Pyridine
  • Imidolactam
  • Organoslifonic acid amide
  • Heteroaromatic compound
  • Organic slifonic acid or derivatives
  • Vinylogous amide
  • Vinylogous acid
  • Thiophene
  • Organoslifonic acid or derivatives
  • Ketone
  • Alkanolamine
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

  • Drug metabolite

    • Biofunction

  • Analgesics
  • Nonsteroidal Anti-inflammatory Agents (NSAIAs)
  • Waste products

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP2.62BIOBYTE STARLIST (2009)

    Predicted Properties

    Property Value Source Water Solubility0.046 mg/mLALOGPS logP2.53ALOGPS logP1.99ChemAxon logS-3.9ALOGPS pKa (Strongest Acidic)6.88ChemAxon pKa (Strongest Basic)4.78ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area99.6 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity97.02 m3·mol-1ChemAxon Polarizability33.77 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

  • Kidney
  • Liver

    • Pathways

    Name SMPDB Link KEGG Link Lornoxicam Action PathwaySMP00700Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06725

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06725

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB06725 DrugBank Metabolite ID

    DBMET00635 Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    4445392 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Lornoxicam NuGOwiki Link

    HMDB15666 Metagene Link

    HMDB15666 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    724428

    Product: Vanoxerine

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. 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:8857077 ]
    2. 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:2284216 ]
    3. Hitzenberger G, Radhofer-Welte S, Takacs F, Rosenow D: Pharmacokinetics of lornoxicam in man. Postgrad Med J. 1990;66 Suppl 4:S22-7. [PubMed:2284217 ]
    4. Olkkola KT, Brunetto AV, Mattila MJ: Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents. Clin Pharmacokinet. 1994 Feb;26(2):107-20. [PubMed:8162655 ]
    5. Vane JR: Introduction: mechanism of action of NSAIDs. Br J Rheumatol. 1996 Apr;35 Suppl 1:1-3. [PubMed:8630629 ]
    6. 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:8706598 ]
    7. Skjodt NM, Davies NM: Clinical pharmacokinetics of lornoxicam. A short half-life oxicam. Clin Pharmacokinet. 1998 Jun;34(6):421-8. [PubMed:9646006 ]
    8. 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:12879104 ]

    Enzymes

    General function:
    Involved in peroxidase activity
    Specific function:
    Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
    Gene Name:
    PTGS2
    Uniprot ID:
    P35354
    Molecular weight:
    68995.625
    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. doi: 10.1016/j.contraception.2009.12.008. Epub 2010 Jan 27. [PubMed:20399943 ]
    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:10450786 ]
    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:17516707 ]
    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:11846620 ]
    General function:
    Involved in peroxidase activity
    Specific function:
    May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
    Gene Name:
    PTGS1
    Uniprot ID:
    P23219
    Molecular weight:
    68685.82
    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. doi: 10.1016/j.contraception.2009.12.008. Epub 2010 Jan 27. [PubMed:20399943 ]
    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:10450786 ]
    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:17516707 ]
    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:11846620 ]
    General function:
    Involved in monooxygenase 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, phenytoin, tolbutamide and losartan.
    Gene Name:
    CYP2C9
    Uniprot ID:
    P11712
    Molecular weight:
    55627.365
    References
    1. 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:16118328 ]
    2. 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:17022718 ]
    3. 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:15606435 ]
    4. 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:10640513 ]
    5. 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:8857077 ]
    6. 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 ]
    7. 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 ]

    PMID: 19956605

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