Posted inUncategorized

Tiagabine

July 24, 2017
Common Name

Tiagabine Description

Tiagabine is an anti-convlisive medication. It is also used in the treatment for panic disorder as are a few other anticonvlisants. Though the exact mechanism by which tiagabine exerts its effect on the human body is unknown, it does appear to operate as a selective GABA reuptake inhibitor. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (-)-(R)-1-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)nipecotic acidChEBI (-)-(R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acidChEBI (R)-(-)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acidChEBI (R)-TiagabineChEBI TiagabinaChEBI TiagabinumChEBI (-)-(R)-1-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)nipecotateGenerator (-)-(R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotateGenerator (R)-(-)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotateGenerator Tiagabine, (S)-isomerMeSH (R)-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)-3-piperidinecarboxylic acid, hydrochlorideMeSH GabitrilMeSH N-(4,4-Di(3-methylthien-2-yl)but-3-enyl)nipecotic acidMeSH

Chemical Formlia

C20H25NO2S2 Average Molecliar Weight

375.548 Monoisotopic Molecliar Weight

375.132670429 IUPAC Name

(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid Traditional Name

tiagabine CAS Registry Number

115103-54-3 SMILES

CC1=C(SC=C1)C(=CCCN1CCC[C@H](C1)C(O)=O)C1=C(C)C=CS1

InChI Identifier

InChI=1S/C20H25NO2S2/c1-14-7-11-24-18(14)17(19-15(2)8-12-25-19)6-4-10-21-9-3-5-16(13-21)20(22)23/h6-8,11-12,16H,3-5,9-10,13H2,1-2H3,(H,22,23)/t16-/m1/s1

InChI Key

PBJUNZJWGZTSKL-MRXNPFEDSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as piperidinecarboxylic acids. These are compounds containing a piperidine ring which bears a carboxylic acid group. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Piperidines Direct Parent

Piperidinecarboxylic acids Alternative Parents

  • Thiophenes
  • Heteroaromatic compounds
  • Trialkylamines
  • Amino acids
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Piperidinecarboxylic acid
  • Thiophene
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Tertiary amine
  • Amino acid
  • Tertiary aliphatic amine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • tertiary amino compound (CHEBI:9586 )
  • thiophenes (CHEBI:9586 )
  • piperidinemonocarboxylic acid (CHEBI:9586 )
  • beta-amino acid (CHEBI:9586 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anticonvlisants
  • GABA Agonists
  • Neuroprotective Agents
  • Neurotransmitter Uptake Inhibitors

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility2.11e-02 g/LNot Available LogP2.6Not Available

    Predicted Properties

    Property Value Source Water Solubility0.021 mg/mLALOGPS logP4.98ALOGPS logP2.6ChemAxon logS-4.2ALOGPS pKa (Strongest Acidic)4.14ChemAxon pKa (Strongest Basic)9.26ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area40.54 Å2ChemAxon Rotatable Bond Count6ChemAxon Refractivity115.32 m3·mol-1ChemAxon Polarizability41.7 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-004j-1769000000-3559976e948cc2135c8cView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00906

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00906

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-3 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-1 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00906 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    54661 KEGG Compound ID

    C07503 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Tiagabine NuGOwiki Link

    HMDB15042 Metagene Link

    HMDB15042 METLIN ID

    Not Available PubChem Compound

    60648 PDB ID

    Not Available ChEBI ID

    222170

    Product: Raltegravir (potassium salt)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
    Gene Name:
    CYP3A4
    Uniprot ID:
    P08684
    Molecular weight:
    57255.585
    References
    1. 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 ]
    General function:
    Involved in neurotransmitter:sodium symporter activity
    Specific function:
    Terminates the action of GABA by its high affinity sodium-dependent reuptake into presynaptic terminals.
    Gene Name:
    SLC6A1
    Uniprot ID:
    P30531
    Molecular weight:
    67073.0
    References
    1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
    2. Pollack MH, Roy-Byrne PP, Van Ameringen M, Snyder H, Brown C, Ondrasik J, Rickels K: The selective GABA reuptake inhibitor tiagabine for the treatment of generalized anxiety disorder: results of a placebo-controlled study. J Clin Psychiatry. 2005 Nov;66(11):1401-8. [PubMed:16420077 ]
    3. Sheehan DV, Sheehan KH, Raj BA, Janavs J: An open-label study of tiagabine in panic disorder. Psychopharmacol Bull. 2007;40(3):32-40. [PubMed:18007567 ]
    4. Foster AC, Kemp JA: Glutamate- and GABA-based CNS therapeutics. Curr Opin Pharmacol. 2006 Feb;6(1):7-17. Epub 2005 Dec 22. [PubMed:16377242 ]
    5. Sunol C, Babot Z, Cristofol R, Sonnewald U, Waagepetersen HS, Schousboe A: A possible role of the non-GAT1 GABA transporters in transfer of GABA from GABAergic to glutamatergic neurons in mouse cerebellar neuronal cultures. Neurochem Res. 2010 Sep;35(9):1384-90. doi: 10.1007/s11064-010-0196-1. Epub 2010 May 30. [PubMed:20512624 ]
    6. Henjum S, Hassel B: High-affinity GABA uptake and GABA-metabolizing enzymes in pig forebrain white matter: a quantitative study. Neurochem Int. 2007 Jan;50(2):365-70. Epub 2006 Oct 27. [PubMed:17069932 ]

    PMID: 20444281

    Last updated on