Posted inUncategorized

Dipyridamole

July 24, 2017
Common Name

Dipyridamole Description

Dipyridamole is only found in individuals that have used or taken this drug. It is a phosphodiesterase inhibitor that blocks uptake and metabolism of adenosine by erythrocytes and vascliar endothelial cells. Dipyridamole also potentiates the antiaggregating action of prostacyclin. (From AMA Drug Evaluations Annual, 1994, p752)Dipyridamole likely inhibits both adenosine deaminase and phosphodiesterase, preventing the degradation of cAMP, an inhibitor of platelet function. This elevation in cAMP blocks the release of arachidonic acid from membrane phospholipids and reduces thromboxane A2 activity. Dipyridamole also directly stimliates the release of prostacyclin, which induces adenylate cyclase activity, thereby raising the intraplatelet concentration of cAMP and further inhibiting platelet aggregation. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source CardoxinChEBI Cleridium 150ChEBI CurantylChEBI DipiridamolChEBI DipyridamineChEBI DipyridamolumChEBI DipyudamineChEBI DypyridamolChEBI PersantinChEBI DipyridamolHMDB Usaf ge-12HMDB Ashbourne brand OF dipyridamoleMeSH Berlin chemie brand OF dipyridamoleMeSH Berlin-chemie brand OF dipyridamoleMeSH CurantilMeSH novo-DipiradolMeSH Novopharm brand OF dipyridamoleMeSH PersantineMeSH Boehringer ingelheim brand OF dipyridamoleMeSH CléridiumMeSH DipyramidoleMeSH AntistenocardinMeSH apo-DipyridamoleMeSH CerebrovaseMeSH MiosenMeSH Apotex brand OF dipyridamoleMeSH Belmac brand OF dipyridamoleMeSH IPRAD brand OF dipyridamoleMeSH KurantilMeSH

Chemical Formlia

C24H40N8O4 Average Molecliar Weight

504.6256 Monoisotopic Molecliar Weight

504.317251808 IUPAC Name

2-({6-[bis(2-hydroxyethyl)amino]-4,8-bis(piperidin-1-yl)-[1,3]diazino[5,4-d]pyrimidin-2-yl}(2-hydroxyethyl)amino)ethan-1-ol Traditional Name

dipyridamole CAS Registry Number

58-32-2 SMILES

OCCN(CCO)C1=NC2=C(N=C(N=C2N2CCCCC2)N(CCO)CCO)C(=N1)N1CCCCC1

InChI Identifier

InChI=1S/C24H40N8O4/c33-15-11-31(12-16-34)23-26-20-19(21(27-23)29-7-3-1-4-8-29)25-24(32(13-17-35)14-18-36)28-22(20)30-9-5-2-6-10-30/h33-36H,1-18H2

InChI Key

IZEKFCXSFNUWAM-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group. Kingdom

Organic compounds Super Class

Organic nitrogen compounds Class

Organonitrogen compounds Sub Class

Amines Direct Parent

Dialkylarylamines Alternative Parents

  • Aminopyrimidines and derivatives
  • Piperidines
  • Imidolactams
  • Heteroaromatic compounds
  • Azacyclic compounds
  • Alkanolamines
  • Primary alcohols
  • Organopnictogen compounds
  • Hydrocarbon derivatives

    • Substituents

  • Dialkylarylamine
  • Aminopyrimidine
  • Piperidine
  • Pyrimidine
  • Imidolactam
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Alkanolamine
  • Azacycle
  • Alcohol
  • Hydrocarbon derivative
  • Primary alcohol
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • piperidines (CHEBI:4653 )
  • tertiary amino compound (CHEBI:4653 )
  • tetrol (CHEBI:4653 )
  • pyrimidopyrimidine (CHEBI:4653 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Phosphodiesterase Inhibitors
  • Platelet Aggregation Inhibitors
  • Vasodilator Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point163 °CNot Available Boiling PointNot AvailableNot Available Water Solubility9.22e-01 g/LNot Available LogP1.5Not Available

    Predicted Properties

    Property Value Source Water Solubility0.92 mg/mLALOGPS logP1.52ALOGPS logP1.81ChemAxon logS-2.7ALOGPS pKa (Strongest Acidic)14.97ChemAxon pKa (Strongest Basic)6.59ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count12ChemAxon Hydrogen Donor Count4ChemAxon Polar Surface Area145.44 Å2ChemAxon Rotatable Bond Count12ChemAxon Refractivity142.78 m3·mol-1ChemAxon Polarizability56.94 Å3ChemAxon Number of Rings4ChemAxon Bioavailability0ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-0udl-0291000000-2fc7956fe6ea13c73317View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-0a4i-0001190000-346cf73a19cbefa2dc11View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-0a4i-0013490000-839580758bc83767be8fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-0udl-0291000000-caeb14eb3ea863e020a0View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-0a4i-1348890000-aa1e3a113b8c2768cb08View 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

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Dipyridamole (Antiplatelet) PathwaySMP00264Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00975

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00975

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00975 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

    2997 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Dipyridamole NuGOwiki Link

    HMDB15110 Metagene Link

    HMDB15110 METLIN ID

    Not Available PubChem Compound

    3108 PDB ID

    Not Available ChEBI ID

    4653

    Product: AGN 195184

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Download (PDF) General References
    1. Diener HC, Cunha L, Forbes C, Sivenius J, Smets P, Lowenthal A: European Stroke Prevention Study. 2. Dipyridamole and acetylsalicylic acid in the secondary prevention of stroke. J Neurol Sci. 1996 Nov;143(1-2):1-13. [PubMed:8981292 ]

    Enzymes

    General function:
    Involved in catalytic activity
    Specific function:
    Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. Can hydrolyze both cAMP and cGMP, but has higher affinity for cAMP and is more efficient with cAMP as substrate.
    Gene Name:
    PDE10A
    Uniprot ID:
    Q9Y233
    Molecular weight:
    89388.7
    References
    1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
    3. Fujishige K, Kotera J, Michibata H, Yuasa K, Takebayashi S, Okumura K, Omori K: Cloning and characterization of a novel human phosphodiesterase that hydrolyzes both cAMP and cGMP (PDE10A). J Biol Chem. 1999 Jun 25;274(26):18438-45. [PubMed:10373451 ]
    General function:
    Involved in 3,5-cyclic-nucleotide phosphodiesterase activity
    Specific function:
    Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes.
    Gene Name:
    PDE4A
    Uniprot ID:
    P27815
    Molecular weight:
    98142.155
    References
    1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
    General function:
    Involved in catalytic activity
    Specific function:
    Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5-GMP.
    Gene Name:
    PDE5A
    Uniprot ID:
    O76074
    Molecular weight:
    99984.14
    References
    1. Kulkarni SK, Patil CS: Phosphodiesterase 5 enzyme and its inhibitors: update on pharmacological and therapeutical aspects. Methods Find Exp Clin Pharmacol. 2004 Dec;26(10):789-99. [PubMed:15672122 ]
    2. Santini F, Casali G, Franchi G, Auriemma S, Lusini M, Barozzi L, Favaro A, Messina A, Mazzucco A: Hemodynamic effects of inhaled nitric oxide and phosphodiesterase inhibitor (dipyridamole) on secondary pulmonary hypertension following heart valve surgery in adults. Int J Cardiol. 2005 Aug 18;103(2):156-63. [PubMed:16080974 ]
    3. Kruuse C, Lassen LH, Iversen HK, Oestergaard S, Olesen J: Dipyridamole may induce migraine in patients with migraine without aura. Cephalalgia. 2006 Aug;26(8):925-33. [PubMed:16886928 ]
    4. Jackson EK, Ren J, Zacharia LC, Mi Z: Characterization of renal ecto-phosphodiesterase. J Pharmacol Exp Ther. 2007 May;321(2):810-5. Epub 2007 Feb 16. [PubMed:17308037 ]
    5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
    General function:
    Involved in deaminase activity
    Specific function:
    Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine. Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events. Acts as a positive regulator of T-cell coactivation, by binding DPP4. Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion.
    Gene Name:
    ADA
    Uniprot ID:
    P00813
    Molecular weight:
    40764.13
    References
    1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

    Transporters

    General function:
    Involved in ATP binding
    Specific function:
    Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
    Gene Name:
    ABCB1
    Uniprot ID:
    P08183
    Molecular weight:
    141477.3
    References
    1. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]
    2. Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [PubMed:11716514 ]
    General function:
    Involved in ATP binding
    Specific function:
    May be an organic anion pump relevant to cellular detoxification
    Gene Name:
    ABCC4
    Uniprot ID:
    O15439
    Molecular weight:
    149525.3
    References
    1. van Aubel RA, Smeets PH, Peters JG, Bindels RJ, Russel FG: The MRP4/ABCC4 gene encodes a novel apical organic anion transporter in human kidney proximal tubules: putative efflux pump for urinary cAMP and cGMP. J Am Soc Nephrol. 2002 Mar;13(3):595-603. [PubMed:11856762 ]
    2. Reid G, Wielinga P, Zelcer N, De Haas M, Van Deemter L, Wijnholds J, Balzarini J, Borst P: Characterization of the transport of nucleoside analog drugs by the human multidrug resistance proteins MRP4 and MRP5. Mol Pharmacol. 2003 May;63(5):1094-103. [PubMed:12695538 ]
    3. Rius M, Nies AT, Hummel-Eisenbeiss J, Jedlitschky G, Keppler D: Cotransport of reduced glutathione with bile salts by MRP4 (ABCC4) localized to the basolateral hepatocyte membrane. Hepatology. 2003 Aug;38(2):374-84. [PubMed:12883481 ]
    General function:
    Involved in ATP binding
    Specific function:
    Acts as a multispecific organic anion pump which can transport nucleotide analogs
    Gene Name:
    ABCC5
    Uniprot ID:
    O15440
    Molecular weight:
    160658.8
    References
    1. Reid G, Wielinga P, Zelcer N, De Haas M, Van Deemter L, Wijnholds J, Balzarini J, Borst P: Characterization of the transport of nucleoside analog drugs by the human multidrug resistance proteins MRP4 and MRP5. Mol Pharmacol. 2003 May;63(5):1094-103. [PubMed:12695538 ]

    PMID: 20516370

    Last updated on