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Identification
NameRidogrel
Accession NumberDB01207  (APRD00271)
TypeSmall Molecule
GroupsApproved
Description

Ridogrel is a dual action drug useful 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.

Structure
Thumb
Synonyms
R-68070
Ridogrel
Ridogrelum
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIQTS5QOO42O
CAS number110140-89-1
WeightAverage: 366.3344
Monoisotopic: 366.119127035
Chemical FormulaC18H17F3N2O3
InChI KeyInChIKey=GLLPUTYLZIKEGF-HAVVHWLPSA-N
InChI
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+
IUPAC Name
5-{[(E)-{pyridin-3-yl[3-(trifluoromethyl)phenyl]methylidene}amino]oxy}pentanoic acid
SMILES
OC(=O)CCCCO\N=C(\C1=CN=CC=C1)C1=CC(=CC=C1)C(F)(F)F
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyridines and derivatives. These are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassNot Available
Direct ParentPyridines and derivatives
Alternative Parents
Substituents
  • Benzenoid
  • Pyridine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Oxime ether
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl fluoride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed as an adjunctive therapy to induce thrombolysis in patients suffering acute myocardial infarction.
PharmacodynamicsRidogrel, a combined thromboxane synthase inhibitor and receptor antagonist, is used with streptokinase as an adjunctive therapy to reduce the formation and size of blood clots. Blood clots can cause ischemic cardiac events (heart attacks). Ridogrel has the dual property of inhibiting the synthesis of thromboxane and blocking the receptors of thromboxane/prostaglandin/endoperoxides. It has been shown to accelerate the speed of recanalization and to delay or prevent reocclusion during systemic thrombolysis with tissue plasminogen activator (streptokinase). Ridogrel is a more potent antiplatelet agent than aspirin and might offer an advantage over aspirin as an adjunct to thrombolysis in patients suffering from acute myocardial infarction. While aspirin inhibits cyclooxygenase, the enzyme responsible for producing thromboxane, ridogrel inhibits thromboxane synthesis directly. A recent comparison between aspirin and ridogrel in as adjunct to thrombolysis in patients with acute myocardial infarction demonstrated that ridogrel is not superior to aspirin in enhancing the fibrinolytic efficacy of streptokinase but might be more effective in preventing new ischemic events. Clinical experience with this drug is still relatively limited.
Mechanism of actionRidogrel 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.
Related Articles
AbsorptionRapidly absorbed after oral administration (30-60 min)
Volume of distributionNot Available
Protein bindingApproximately 60% bound to plasma proteins
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9925
Blood Brain Barrier+0.9613
Caco-2 permeable-0.5694
P-glycoprotein substrateNon-substrate0.5312
P-glycoprotein inhibitor INon-inhibitor0.6419
P-glycoprotein inhibitor IINon-inhibitor0.8893
Renal organic cation transporterNon-inhibitor0.5991
CYP450 2C9 substrateNon-substrate0.8073
CYP450 2D6 substrateNon-substrate0.7912
CYP450 3A4 substrateNon-substrate0.5846
CYP450 1A2 substrateNon-inhibitor0.5
CYP450 2C9 inhibitorNon-inhibitor0.6234
CYP450 2D6 inhibitorNon-inhibitor0.839
CYP450 2C19 inhibitorNon-inhibitor0.5103
CYP450 3A4 inhibitorNon-inhibitor0.7368
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7691
Ames testNon AMES toxic0.6001
CarcinogenicityNon-carcinogens0.864
BiodegradationNot ready biodegradable0.9938
Rat acute toxicity2.5990 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9916
hERG inhibition (predictor II)Non-inhibitor0.6611
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP4.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00839 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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AbciximabAbciximab may increase the anticoagulant activities of Ridogrel.
AcenocoumarolRidogrel may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidAcetylsalicylic acid may increase the anticoagulant activities of Ridogrel.
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Aminosalicylic Acid is combined with Ridogrel.
AnagrelideAnagrelide may increase the anticoagulant activities of Ridogrel.
ApixabanRidogrel may increase the anticoagulant activities of Apixaban.
AprotininThe therapeutic efficacy of Ridogrel can be decreased when used in combination with Aprotinin.
ArgatrobanRidogrel may increase the anticoagulant activities of Argatroban.
Bismuth SubsalicylateThe risk or severity of adverse effects can be increased when Bismuth Subsalicylate is combined with Ridogrel.
BivalirudinRidogrel may increase the anticoagulant activities of Bivalirudin.
CaffeineCaffeine may increase the anticoagulant activities of Ridogrel.
CangrelorCangrelor may increase the anticoagulant activities of Ridogrel.
CilostazolCilostazol may increase the anticoagulant activities of Ridogrel.
CitalopramCitalopram may increase the anticoagulant activities of Ridogrel.
ClopidogrelClopidogrel may increase the anticoagulant activities of Ridogrel.
Dabigatran etexilateRidogrel may increase the anticoagulant activities of Dabigatran etexilate.
DalteparinRidogrel may increase the anticoagulant activities of Dalteparin.
DanaparoidRidogrel may increase the anticoagulant activities of Danaparoid.
DesirudinRidogrel may increase the anticoagulant activities of Desirudin.
DesvenlafaxineDesvenlafaxine may increase the anticoagulant activities of Ridogrel.
DiclofenacDiclofenac may increase the anticoagulant activities of Ridogrel.
DiflunisalDiflunisal may increase the anticoagulant activities of Ridogrel.
DihydrocodeineDihydrocodeine may increase the anticoagulant activities of Ridogrel.
DipyridamoleDipyridamole may increase the anticoagulant activities of Ridogrel.
DuloxetineDuloxetine may increase the anticoagulant activities of Ridogrel.
EdoxabanRidogrel may increase the anticoagulant activities of Edoxaban.
EnoxaparinRidogrel may increase the anticoagulant activities of Enoxaparin.
EpoprostenolThe risk or severity of adverse effects can be increased when Ridogrel is combined with Epoprostenol.
EptifibatideEptifibatide may increase the anticoagulant activities of Ridogrel.
EscitalopramEscitalopram may increase the anticoagulant activities of Ridogrel.
EtodolacEtodolac may increase the anticoagulant activities of Ridogrel.
FenoprofenFenoprofen may increase the anticoagulant activities of Ridogrel.
FloctafenineFloctafenine may increase the anticoagulant activities of Ridogrel.
FluoxetineFluoxetine may increase the anticoagulant activities of Ridogrel.
FlurbiprofenFlurbiprofen may increase the anticoagulant activities of Ridogrel.
FluvoxamineFluvoxamine may increase the anticoagulant activities of Ridogrel.
Fondaparinux sodiumRidogrel may increase the anticoagulant activities of Fondaparinux sodium.
HeparinRidogrel may increase the anticoagulant activities of Heparin.
IbuprofenIbuprofen may increase the anticoagulant activities of Ridogrel.
IloprostThe risk or severity of adverse effects can be increased when Ridogrel is combined with Iloprost.
IndomethacinIndomethacin may increase the anticoagulant activities of Ridogrel.
KetoprofenKetoprofen may increase the anticoagulant activities of Ridogrel.
KetorolacKetorolac may increase the anticoagulant activities of Ridogrel.
LevomilnacipranLevomilnacipran may increase the anticoagulant activities of Ridogrel.
Magnesium salicylateThe risk or severity of adverse effects can be increased when Magnesium salicylate is combined with Ridogrel.
Mefenamic acidMefenamic acid may increase the anticoagulant activities of Ridogrel.
MeloxicamMeloxicam may increase the anticoagulant activities of Ridogrel.
MilnacipranMilnacipran may increase the anticoagulant activities of Ridogrel.
NabumetoneNabumetone may increase the anticoagulant activities of Ridogrel.
NadroparinRidogrel may increase the anticoagulant activities of Nadroparin.
NaproxenNaproxen may increase the anticoagulant activities of Ridogrel.
OxaprozinOxaprozin may increase the anticoagulant activities of Ridogrel.
ParoxetineParoxetine may increase the anticoagulant activities of Ridogrel.
PiroxicamPiroxicam may increase the anticoagulant activities of Ridogrel.
PrasugrelPrasugrel may increase the anticoagulant activities of Ridogrel.
RivaroxabanRidogrel may increase the anticoagulant activities of Rivaroxaban.
SalsalateThe risk or severity of adverse effects can be increased when Salsalate is combined with Ridogrel.
SertralineSertraline may increase the anticoagulant activities of Ridogrel.
SulindacSulindac may increase the anticoagulant activities of Ridogrel.
Tiaprofenic acidTiaprofenic acid may increase the anticoagulant activities of Ridogrel.
TicagrelorTicagrelor may increase the anticoagulant activities of Ridogrel.
TiclopidineTiclopidine may increase the anticoagulant activities of Ridogrel.
TinzaparinRidogrel may increase the anticoagulant activities of Tinzaparin.
TirofibanTirofiban may increase the anticoagulant activities of Ridogrel.
TolmetinTolmetin may increase the anticoagulant activities of Ridogrel.
TreprostinilThe risk or severity of adverse effects can be increased when Ridogrel is combined with Treprostinil.
VenlafaxineVenlafaxine may increase the anticoagulant activities of Ridogrel.
VilazodoneVilazodone may increase the anticoagulant activities of Ridogrel.
VorapaxarVorapaxar may increase the anticoagulant activities of Ridogrel.
VortioxetineVortioxetine may increase the anticoagulant activities of Ridogrel.
WarfarinRidogrel may increase the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Thromboxane-a synthase activity
Specific Function:
Not Available
Gene Name:
TBXAS1
Uniprot ID:
P24557
Molecular Weight:
60517.69 Da
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 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Thromboxane a2 receptor activity
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 ...
Gene Name:
TBXA2R
Uniprot ID:
P21731
Molecular Weight:
37430.69 Da
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23