Ridogrel

Common Name

Ridogrel Description

Ridogrel is only found in individuals that have used or taken this drug. It is a dual action drug usefli for the prevention of systemic thrombo-embolism and as an adjunctive agent to thrombolytic therapy in acute myocardial infarction. However, there currently are no clinical indications for preferential use of ridogrel over aspirin.Ridogrel inhibits thromboxane A2 synthase and also blocks the thromboxane A2/prostaglandin endoperoxide receptors. Thromboxane synthetase produces thromboxane in platelets. Thromboxane is a vasoconstrictor and facilitates the clumping of platelets. Therefore by inhibiting the production and promotion of thromboxane, thrombolysis is enhanced. Structure

Synonyms

Value Source 5-((((3-Pyridinyl)(3-(trifluoromethyl)phenyl)methylene)amino)oxy)pentanoic acidMeSH

Chemical Formlia

C18H17F3N2O3 Average Molecliar Weight

366.3344 Monoisotopic Molecliar Weight

366.119127035 IUPAC Name

5-{[(E)-{pyridin-3-yl[3-(trifluoromethyl)phenyl]methylidene}amino]oxy}pentanoic acid Traditional Name

ridogrel CAS Registry Number

110140-89-1 SMILES

OC(=O)CCCCON=C(C1=CN=CC=C1)C1=CC(=CC=C1)C(F)(F)F

InChI Identifier

InChI=1S/C18H17F3N2O3/c19-18(20,21)15-7-3-5-13(11-15)17(14-6-4-9-22-12-14)23-26-10-2-1-8-16(24)25/h3-7,9,11-12H,1-2,8,10H2,(H,24,25)/b23-17+

InChI Key

GLLPUTYLZIKEGF-HAVVHWLPSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Trifluoromethylbenzenes Alternative Parents

  • Pyridines and derivatives
  • Heteroaromatic compounds
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organonitrogen compounds
  • Organofluorides
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds
  • Alkyl fluorides
  • Substituents

  • Trifluoromethylbenzene
  • Pyridine
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Alkyl fluoride
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Alkyl halide
  • Aromatic heteromonocyclic compound
  • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug
  • Biofunction

  • Enzyme Inhibitors
  • Gastrointestinal Agents
  • Platelet Aggregation Inhibitors
  • Thrombolytic Agents
  • Application

  • Pharmaceutical
  • Cellliar locations

  • Membrane
  • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility8.39e-03 g/LNot Available LogP4.3Not Available

    Predicted Properties

    Property Value Source Water Solubility0.0084 mg/mLALOGPS logP3.24ALOGPS logP3.13ChemAxon logS-4.6ALOGPS pKa (Strongest Acidic)3.5ChemAxon pKa (Strongest Basic)4.26ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area71.78 Å2ChemAxon Rotatable Bond Count9ChemAxon Refractivity88.89 m3·mol-1ChemAxon Polarizability34.94 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key 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 DB01207

  • 21059682
  • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01207

  • 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

    DB01207 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

    4515025 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB15338 Metagene Link

    HMDB15338 METLIN ID

    Not Available PubChem Compound

    5362391 PDB ID

    Not Available ChEBI ID

    127439

    Product: Ingenol Mebutate

    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:
    Not Available
    Gene Name:
    TBXAS1
    Uniprot ID:
    P24557
    Molecular weight:
    60648.885
    References
    1. Park SJ, Lee JJ, Vanhoutte PM: Endothelin-1 releases endothelium-derived endoperoxides and thromboxane A2 in porcine coronary arteries with regenerated endothelium. Zhongguo Yao Li Xue Bao. 1999 Oct;20(10):872-8. [PubMed:11270983 ]
    2. Tytgat GN, Van Nueten L, Van De Velde I, Joslyn A, Hanauer SB: Efficacy and safety of oral ridogrel in the treatment of ulcerative colitis: two multicentre, randomized, double-blind studies. Aliment Pharmacol Ther. 2002 Jan;16(1):87-99. [PubMed:11856082 ]
    3. Authors unspecified: Randomized trial of ridogrel, a combined thromboxane A2 synthase inhibitor and thromboxane A2/prostaglandin endoperoxide receptor antagonist, versus aspirin as adjunct to thrombolysis in patients with acute myocardial infarction. The Ridogrel Versus Aspirin Patency Trial (RAPT). Circulation. 1994 Feb;89(2):588-95. [PubMed:8313547 ]
    4. De Cree J, Geukens H, Gutwirth P, De Clerck F, Vercammen E, Verhaegen H: The effect of a combined administration of ridogrel and ketanserin in patients with intermittent claudication. Int Angiol. 1993 Mar;12(1):59-68. [PubMed:8376914 ]
    5. Carty E, Macey M, McCartney SA, Rampton DS: Ridogrel, a dual thromboxane synthase inhibitor and receptor antagonist: anti-inflammatory profile in inflammatory bowel disease. Aliment Pharmacol Ther. 2000 Jun;14(6):807-17. [PubMed:10848666 ]
    6. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Receptor for thromboxane A2 (TXA2), a potent stimulator of platelet aggregation. The activity of this receptor is mediated by a G-protein that activates a phosphatidylinositol-calcium second messenger system. In the kidney, the binding of TXA2 to glomerular TP receptors causes intense vasoconstriction. Activates phospholipase C. Isoform 1 activates adenylyl cyclase. Isoform 2 inhibits adenylyl cyclase
    Gene Name:
    TBXA2R
    Uniprot ID:
    P21731
    Molecular weight:
    37430.7
    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. Heinisch G, Holzer W, Kunz F, Langer T, Lukavsky P, Pechlaner C, Weissenberger H: On the bioisosteric potential of diazines: diazine analogues of the combined thromboxane A2 receptor antagonist and synthetase inhibitor Ridogrel. J Med Chem. 1996 Sep 27;39(20):4058-64. [PubMed:8831771 ]
    3. Soyka R, Heckel A, Nickl J, Eisert W, Muller TH, Weisenberger H: 6,6-Disubstituted Hex-5-enoic acid derivatives as combined thromboxane A2 receptor antagonists and synthetase inhibitors. J Med Chem. 1994 Jan 7;37(1):26-39. [PubMed:8289199 ]
    4. Hempelmann RG, Pradel RH, Mehdorn HM, Ziegler A: Threshold concentrations of endothelin-1: the effects on contractions induced by 5-hydroxytryptamine in isolated rat cerebral and mesenteric arteries. Pharmacol Toxicol. 1999 Sep;85(3):115-22. [PubMed:10522750 ]
    5. Carvalho MH, Fortes ZB, Nigro D, Oliveira MA, Scivoletto R: The role of thromboxane A2 in the altered microvascular reactivity in two-kidney, one-clip hypertension. Endothelium. 1997;5(3):167-78. [PubMed:9272380 ]
    6. Ragni M, Golino P, Cirillo P, Pascucci I, Scognamiglio A, Ravera A, Esposito N, Battaglia C, Guarino A, Chiariello M: [Inactivated factor VII exercises a powerful antithrombotic activity in an experimental model of recurrent arterial thrombosis]. Cardiologia. 1996 Jan;41(1):51-8. [PubMed:8697470 ]

    PMID: 21859929