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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyRidogrel
Identification
- Name
- Ridogrel
- Accession Number
- DB01207 (APRD00271)
- Type
- Small Molecule
- Groups
- Experimental
- 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
Structure for Ridogrel (DB01207)
- Synonyms
- Ridogrelum
- External IDs
- R 68070 / R-68070
- Categories
- UNII
- QTS5QOO42O
- CAS number
- 110140-89-1
- Weight
- Average: 366.3344
Monoisotopic: 366.119127035 - Chemical Formula
- C18H17F3N2O3
- InChI Key
- 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
Pharmacology
- Indication
Used as an adjunctive therapy to induce thrombolysis in patients suffering acute myocardial infarction.
- Pharmacodynamics
Ridogrel, 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 action
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.
Target Actions Organism AThromboxane A2 receptor antagonistHumans AThromboxane-A synthase inhibitorHumans - Absorption
Rapidly absorbed after oral administration (30-60 min)
- Volume of distribution
- Not Available
- Protein binding
Approximately 60% bound to plasma proteins
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half life
- Not Available
- Clearance
- Not Available
- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional Data(R)-warfarin The risk or severity of bleeding can be increased when Ridogrel is combined with (R)-warfarin. (S)-Warfarin The risk or severity of bleeding can be increased when Ridogrel is combined with (S)-Warfarin. 4-hydroxycoumarin The risk or severity of bleeding can be increased when Ridogrel is combined with 4-hydroxycoumarin. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline The risk or severity of bleeding and hemorrhage can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Ridogrel. Abciximab The risk or severity of bleeding can be increased when Ridogrel is combined with Abciximab. Aceclofenac The risk or severity of bleeding can be increased when Aceclofenac is combined with Ridogrel. Acemetacin The risk or severity of bleeding can be increased when Acemetacin is combined with Ridogrel. Acenocoumarol The risk or severity of bleeding can be increased when Ridogrel is combined with Acenocoumarol. Acetylsalicylic acid Acetylsalicylic acid may increase the antiplatelet activities of Ridogrel. Alaproclate The risk or severity of hemorrhage can be increased when Alaproclate is combined with Ridogrel. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015338
- PubChem Compound
- 5362391
- PubChem Substance
- 46506774
- ChemSpider
- 4515025
- BindingDB
- 50003795
- ChEBI
- 135542
- ChEMBL
- CHEMBL280728
- ZINC
- ZINC000001536934
- Therapeutic Targets Database
- DAP000469
- PharmGKB
- PA164746413
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 4.3 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00839 mg/mL ALOGPS logP 3.24 ALOGPS logP 3.13 ChemAxon logS -4.6 ALOGPS pKa (Strongest Acidic) 3.5 ChemAxon pKa (Strongest Basic) 4.26 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 71.78 Å2 ChemAxon Rotatable Bond Count 9 ChemAxon Refractivity 88.89 m3·mol-1 ChemAxon Polarizability 34.94 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9925 Blood Brain Barrier + 0.9613 Caco-2 permeable - 0.5694 P-glycoprotein substrate Non-substrate 0.5312 P-glycoprotein inhibitor I Non-inhibitor 0.6419 P-glycoprotein inhibitor II Non-inhibitor 0.8893 Renal organic cation transporter Non-inhibitor 0.5991 CYP450 2C9 substrate Non-substrate 0.8073 CYP450 2D6 substrate Non-substrate 0.7912 CYP450 3A4 substrate Non-substrate 0.5846 CYP450 1A2 substrate Non-inhibitor 0.5 CYP450 2C9 inhibitor Non-inhibitor 0.6234 CYP450 2D6 inhibitor Non-inhibitor 0.839 CYP450 2C19 inhibitor Non-inhibitor 0.5103 CYP450 3A4 inhibitor Non-inhibitor 0.7368 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7691 Ames test Non AMES toxic 0.6001 Carcinogenicity Non-carcinogens 0.864 Biodegradation Not ready biodegradable 0.9938 Rat acute toxicity 2.5990 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9916 hERG inhibition (predictor II) Non-inhibitor 0.6611
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Trifluoromethylbenzenes
- 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 show 2 more
- Substituents
- Trifluoromethylbenzene / Pyridine / Heteroaromatic compound / Carboxylic acid derivative / Carboxylic acid / Monocarboxylic acid or derivatives / Organoheterocyclic compound / Azacycle / Alkyl fluoride / Hydrocarbon derivative show 11 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- 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 messen...
- Gene Name
- TBXA2R
- Uniprot ID
- P21731
- Uniprot Name
- Thromboxane A2 receptor
- Molecular Weight
- 37430.69 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- 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]
- 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]
- 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]
- 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]
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Thromboxane-a synthase activity
- Specific Function
- Not Available
- Gene Name
- TBXAS1
- Uniprot ID
- P24557
- Uniprot Name
- Thromboxane-A synthase
- Molecular Weight
- 60517.69 Da
References
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
Drug created on June 13, 2005 07:24 / Updated on April 02, 2020 01:56
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