Ridogrel - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (2)

Targets (2)Biointeractions (1)

Identification

Name

Ridogrel

Accession Number

DB01207 (APRD00271)

Type

Small Molecule

Groups

Approved

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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

R-68070

Ridogrel

Ridogrelum

External IDs

Not Available

Product Ingredients

Not Available

Approved Prescription Products

Not Available

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Not Available

Brand mixtures

Not Available

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.

Structured Indications

Not Available

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	Kind	Pharmacological action	Actions	Organism	UniProt ID
Thromboxane-A synthase	Protein	yes	inhibitor	Human	P24557	details
Thromboxane A2 receptor	Protein	yes	antagonist	Human	P21731	details

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

Drug	Interaction	Drug group
Abciximab	Ridogrel may increase the anticoagulant activities of Abciximab.	Approved
Acenocoumarol	Ridogrel may increase the anticoagulant activities of Acenocoumarol.	Approved
Acetylsalicylic acid	The risk or severity of adverse effects can be increased when Ridogrel is combined with Acetylsalicylic acid.	Approved, Vet Approved
Alprostadil	Alprostadil may increase the antiplatelet activities of Ridogrel.	Approved, Investigational
Alteplase	Ridogrel may increase the anticoagulant activities of Alteplase.	Approved
Aminosalicylic Acid	The risk or severity of adverse effects can be increased when Ridogrel is combined with Aminosalicylic Acid.	Approved
Anagrelide	Ridogrel may increase the anticoagulant activities of Anagrelide.	Approved
Ancrod	Ridogrel may increase the anticoagulant activities of Ancrod.	Investigational
Anistreplase	Ridogrel may increase the anticoagulant activities of Anistreplase.	Approved
Antithrombin III human	Ridogrel may increase the anticoagulant activities of Antithrombin III human.	Approved
Apixaban	The risk or severity of adverse effects can be increased when Ridogrel is combined with Apixaban.	Approved
Ardeparin	Ridogrel may increase the anticoagulant activities of Ardeparin.	Approved, Withdrawn
Argatroban	Ridogrel may increase the anticoagulant activities of Argatroban.	Approved, Investigational
Azelastine	Azelastine may increase the antiplatelet activities of Ridogrel.	Approved
Balsalazide	The risk or severity of adverse effects can be increased when Ridogrel is combined with Balsalazide.	Approved, Investigational
Becaplermin	Ridogrel may increase the anticoagulant activities of Becaplermin.	Approved, Investigational
Bemiparin	Ridogrel may increase the anticoagulant activities of Bemiparin.	Approved
Beraprost	Ridogrel may increase the anticoagulant activities of Beraprost.	Investigational
Bivalirudin	Ridogrel may increase the anticoagulant activities of Bivalirudin.	Approved, Investigational
Cangrelor	Ridogrel may increase the anticoagulant activities of Cangrelor.	Approved
Certoparin	Ridogrel may increase the anticoagulant activities of Certoparin.	Approved
Cilostazol	Ridogrel may increase the anticoagulant activities of Cilostazol.	Approved
Citric Acid	Ridogrel may increase the anticoagulant activities of Citric Acid.	Nutraceutical, Vet Approved
Clopidogrel	Ridogrel may increase the anticoagulant activities of Clopidogrel.	Approved, Nutraceutical
Dabigatran etexilate	Ridogrel may increase the anticoagulant activities of Dabigatran etexilate.	Approved
Dalteparin	Ridogrel may increase the anticoagulant activities of Dalteparin.	Approved
Dasatinib	Dasatinib may increase the anticoagulant activities of Ridogrel.	Approved, Investigational
Defibrotide	Ridogrel may increase the anticoagulant activities of Defibrotide.	Approved, Investigational
Deoxycholic Acid	The risk or severity of adverse effects can be increased when Ridogrel is combined with Deoxycholic Acid.	Approved
Desirudin	Ridogrel may increase the anticoagulant activities of Desirudin.	Approved
Desmoteplase	Ridogrel may increase the anticoagulant activities of Desmoteplase.	Investigational
Dextran	Ridogrel may increase the anticoagulant activities of Dextran.	Approved, Vet Approved
Dextran 40	Ridogrel may increase the anticoagulant activities of Dextran 40.	Approved
Dicoumarol	Ridogrel may increase the anticoagulant activities of Dicoumarol.	Approved
Diflunisal	The risk or severity of adverse effects can be increased when Ridogrel is combined with Diflunisal.	Approved
Dipyridamole	Ridogrel may increase the anticoagulant activities of Dipyridamole.	Approved
Ditazole	Ridogrel may increase the anticoagulant activities of Ditazole.	Approved, Withdrawn
Drotrecogin alfa	Ridogrel may increase the anticoagulant activities of Drotrecogin alfa.	Approved, Investigational, Withdrawn
Edetic Acid	Ridogrel may increase the anticoagulant activities of Edetic Acid.	Approved, Vet Approved
Edoxaban	Ridogrel may increase the anticoagulant activities of Edoxaban.	Approved
Enoxaparin	Ridogrel may increase the anticoagulant activities of Enoxaparin.	Approved
Epinastine	Epinastine may increase the antiplatelet activities of Ridogrel.	Approved, Investigational
Epoprostenol	Epoprostenol may increase the antiplatelet activities of Ridogrel.	Approved
Eptifibatide	Ridogrel may increase the anticoagulant activities of Eptifibatide.	Approved, Investigational
Ethyl biscoumacetate	Ridogrel may increase the anticoagulant activities of Ethyl biscoumacetate.	Withdrawn
Fibrinolysin	Ridogrel may increase the anticoagulant activities of Plasmin.	Investigational
Fondaparinux sodium	Ridogrel may increase the anticoagulant activities of Fondaparinux sodium.	Approved, Investigational
Gabexate	Ridogrel may increase the anticoagulant activities of Gabexate.	Investigational
Glucosamine	Glucosamine may increase the antiplatelet activities of Ridogrel.	Approved
Heparin	Ridogrel may increase the anticoagulant activities of Heparin.	Approved, Investigational
Ibritumomab tiuxetan	The risk or severity of adverse effects can be increased when Ridogrel is combined with Ibritumomab tiuxetan.	Approved
Ibrutinib	The risk or severity of adverse effects can be increased when Ibrutinib is combined with Ridogrel.	Approved
Ibudilast	Ridogrel may increase the antiplatelet activities of Ibudilast.	Approved, Investigational
Icosapent ethyl	Ridogrel may increase the antiplatelet activities of Icosapent ethyl.	Approved, Nutraceutical
Ifenprodil	Ridogrel may increase the antiplatelet activities of Ifenprodil.	Approved, Withdrawn
Iloprost	Iloprost may increase the antiplatelet activities of Ridogrel.	Approved, Investigational
Lepirudin	Ridogrel may increase the anticoagulant activities of Lepirudin.	Approved
Limaprost	Limaprost may increase the antiplatelet activities of Ridogrel.	Approved
Mesalazine	The risk or severity of adverse effects can be increased when Ridogrel is combined with Mesalazine.	Approved
Milrinone	Milrinone may increase the antiplatelet activities of Ridogrel.	Approved
Nadroparin	Ridogrel may increase the anticoagulant activities of Nadroparin.	Approved
Nafamostat	Ridogrel may increase the anticoagulant activities of Nafamostat.	Approved, Investigational
NCX 4016	The risk or severity of adverse effects can be increased when Ridogrel is combined with NCX 4016.	Investigational
Nimesulide	Ridogrel may increase the antiplatelet activities of Nimesulide.	Approved, Withdrawn
Obinutuzumab	The risk or severity of adverse effects can be increased when Ridogrel is combined with Obinutuzumab.	Approved
Olsalazine	The risk or severity of adverse effects can be increased when Ridogrel is combined with Olsalazine.	Approved
Omega-3 fatty acids	Omega-3 fatty acids may increase the antiplatelet activities of Ridogrel.	Approved, Nutraceutical
Parnaparin	Ridogrel may increase the anticoagulant activities of Parnaparin.	Approved
Pentosan Polysulfate	The risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Ridogrel.	Approved
Pentoxifylline	Pentoxifylline may increase the antiplatelet activities of Ridogrel.	Approved, Investigational
Phenindione	Ridogrel may increase the anticoagulant activities of Phenindione.	Approved
Phenprocoumon	Ridogrel may increase the anticoagulant activities of Phenprocoumon.	Approved
Prasugrel	Ridogrel may increase the anticoagulant activities of Prasugrel.	Approved
Protein S human	Ridogrel may increase the anticoagulant activities of Protein S human.	Approved
Resveratrol	Ridogrel may increase the antiplatelet activities of Resveratrol.	Experimental, Investigational
Reteplase	Ridogrel may increase the anticoagulant activities of Reteplase.	Approved
Reviparin	Ridogrel may increase the anticoagulant activities of Reviparin.	Approved
Rivaroxaban	Ridogrel may increase the anticoagulant activities of Rivaroxaban.	Approved
Rosiglitazone	Ridogrel may increase the anticoagulant activities of Rosiglitazone.	Approved, Investigational
Salicylic acid	The risk or severity of adverse effects can be increased when Ridogrel is combined with Salicylic acid.	Approved, Vet Approved
Selexipag	Ridogrel may increase the anticoagulant activities of Selexipag.	Approved
Sevoflurane	Ridogrel may increase the antiplatelet activities of Sevoflurane.	Approved, Vet Approved
SRT501	Ridogrel may increase the antiplatelet activities of SRT501.	Investigational
Streptokinase	Ridogrel may increase the anticoagulant activities of Streptokinase.	Approved
Sulodexide	Ridogrel may increase the anticoagulant activities of Sulodexide.	Approved, Investigational
Tenecteplase	Ridogrel may increase the anticoagulant activities of Tenecteplase.	Approved
Tesmilifene	Ridogrel may increase the antiplatelet activities of Tesmilifene.	Investigational
Ticagrelor	Ridogrel may increase the anticoagulant activities of Ticagrelor.	Approved
Ticlopidine	Ridogrel may increase the anticoagulant activities of Ticlopidine.	Approved
Tinzaparin	Ridogrel may increase the anticoagulant activities of Tinzaparin.	Approved
Tipranavir	Tipranavir may increase the antiplatelet activities of Ridogrel.	Approved, Investigational
Tirofiban	Ridogrel may increase the anticoagulant activities of Tirofiban.	Approved
Tositumomab	The risk or severity of adverse effects can be increased when Ridogrel is combined with Tositumomab.	Approved
Tranilast	Ridogrel may increase the antiplatelet activities of Tranilast.	Approved, Investigational
Trapidil	Ridogrel may increase the antiplatelet activities of Trapidil.	Approved
Treprostinil	Treprostinil may increase the antiplatelet activities of Ridogrel.	Approved, Investigational
Triflusal	Ridogrel may increase the anticoagulant activities of Triflusal.	Approved
Urokinase	Ridogrel may increase the anticoagulant activities of Urokinase.	Approved, Investigational, Withdrawn
Vitamin E	Vitamin E may increase the antiplatelet activities of Ridogrel.	Approved, Nutraceutical, Vet Approved
Vorapaxar	Ridogrel may increase the anticoagulant activities of Vorapaxar.	Approved
Warfarin	Ridogrel may increase the anticoagulant activities of Warfarin.	Approved
Ximelagatran	Ridogrel may increase the anticoagulant activities of Ximelagatran.	Approved, Investigational, Withdrawn

Food Interactions

Not Available

References

Synthesis Reference

Not Available

General References

Not Available

External Links

Resource	Link
Human Metabolome Database (HMDB)	HMDB15338
PubChem Compound	5362391
PubChem Substance	46506774
ChemSpider	4515025
BindingDB	50003795
ChEBI	135542
ChEMBL	CHEMBL280728
Therapeutic Targets Database	DAP000469
PharmGKB	PA164746413

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Clinical Trials

Not Available

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	Yes	ChemAxon
MDDR-like Rule	Yes	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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

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

Substituents

Trifluoromethylbenzene / Pyridine / Heteroaromatic compound / Carboxylic acid derivative / Carboxylic acid / Monocarboxylic acid or derivatives / Organoheterocyclic compound / Azacycle / Alkyl fluoride / Hydrocarbon derivative

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Targets

Details

1. Thromboxane-A synthase

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

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 ]

Details

2. Thromboxane A2 receptor

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

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 ]

Drug created on June 13, 2005 07:24 / Updated on June 11, 2017 15:48

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Structure for DB01207 (Ridogrel)

Targets

References

References