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Showing drug card for Ridogrel (DB01207)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:08:21
Primary Accession Number DB01207
Secondary Accession Number
  • APRD00271
Name Ridogrel
Drug Type
  • Approved
  • Small Molecule
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.
Synonyms
  1. Ridogrelum [INN-Latin]
Brand Names Not Available
Brand Mixtures Not Available
Chemical IUPAC Name 5-[[pyridin-3-yl-[3-(trifluoromethyl)phenyl]methylidene]amino]oxypentanoic acid
Chemical Formula C18H17F3N2O3
Chemical Structure Structure
CAS Registry Number 110140-89-1
InChI Identifier InChI=1/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+/f/h24H
InChI Key GLLPUTYLZIKEGF-OLGYSSRVDM
KEGG Drug Not Available
KEGG Compound Not Available
PubChem Compound 5362391 Link Image
PubChem Substance 196719 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link Not Available
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 366.3344
Monoisotopic Molecular Weight 366.1191
State Solid
Melting Point Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 8.39e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 4.3 Source: PhysProp
Predicted LogP 3.24 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.64 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES OC(=O)CCCCO\N=C(\C1=CN=CC=C1)C1=CC(=CC=C1)C(F)(F)F
Canonical SMILES OC(=O)CCCCON=C(C1=CN=CC=C1)C1=CC(=CC=C1)C(F)(F)F
Drug Category
  • Enzyme Inhibitors
  • Gastrointestinal Agents
  • Platelet Aggregation Inhibitors
  • Thrombolytic Agents
ATC Codes Not Available
AHFS Codes Not Available
Indication Used as an adjunctive therapy to induce thrombolysis in patients suffering acute myocardial infarction.
Pharmacology 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 reduced.
Absorption Rapidly absorbed after oral administration (30-60 min)
Toxicity Not Available
Protein Binding Approximately 60% bound to plasma proteins
Biotransformation Not Available
Half Life Not Available
Dosage Forms Not Available
Patient Information Not Available
Contraindications Not Available
Interactions Not Available
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References Not Available
Organisms Affected
  • Humans and other mammals
Targets
  1. Thromboxane A2 synthase
  2. Thromboxane A2 receptor
Drug Target 1 [top]
Target 1 ID 736
Target 1 Name Thromboxane A2 synthase
Target 1 Synonyms Not Available
Target 1 Gene Name TBXAS1
Target 1 Protein Sequence >Thromboxane A2 synthase 
MMEALGFLKLEVNGPMVTVALSVALLALLKWYSTSAFSRLEKLGLRHPKPSPFIGNLTFF
RQGFWESQMELRKLYGPLCGYYLGRRMFIVISEPDMIKQVLVENFSNFTNRMASGLEFKS
VADSVLFLRDKRWEEVRGALMSAFSPEKVNEMVPLISQACDLLLAHLKRYAESGDAFDIQ
RCYCNYTTDVVASVRFGTPVDSWQAPEDPFVKHCKRFFEFCIPRPILVLLLSFPSIMVPL
ARILPNKNRDELNGFFNKLIRNVIALRDQQAAEERRRDFLQMVLDARHSASPMGVQDFDI
VRDVFSSTGCKPNPSRQHQPSPMARPLTVDEIVGQAFIFLIAGYEIITNTLSFATYLLAT
NPDCQEKLLREVDVFKEKHMAPEFCSLEEGLPYLDMVIAETLRMYPPAFRFTREAAQDCE
VLGQRIPAGAVLEMAGGCPAP
Target 1 Number of Residues 448
Target 1 Molecular Weight 50028
Target 1 Theoretical pI 6.76
Target 1 GO Classification
Function
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
tetrapyrrole binding
heme binding
binding
ion binding
cation binding
transition metal ion binding
iron ion binding
catalytic activity
oxidoreductase activity
monooxygenase activity
Process
physiological process
metabolism
cellular metabolism
generation of precursor metabolites and energy
electron transport
Component
Not Available
Target 1 General Function Secondary metabolites biosynthesis, transport and catabolism
Target 1 Specific Function Not Available
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 2833517 Link Image
Target 1 UniProtKB/Swiss-Prot ID O14987 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name O14987_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location Not Available
Target 1 Gene Sequence >1326 bp 
ATGATGGAAGCCTTGGGGTTTCTAAAATTGGAAGTGAATGGCCCCATGGTGACGGTGGCC
CTGTCAGTGGCTCTCTTGGCCCTCCTGAAATGGTACTCCACATCAGCATTCTCAAGACTG
GAGAAGTTAGGCCTCAGACATCCCAAGCCTTCTCCTTTCATTGGAAACTTGACATTTTTC
CGCCAGGGTTTTTGGGAAAGCCAAATGGAGCTCAGAAAGCTGTATGGACCTCTGTGTGGG
TACTATCTTGGTCGTCGGATGTTTATTGTTATTTCTGAGCCAGACATGATCAAGCAGGTG
TTGGTTGAGAACTTCAGTAACTTTACCAACAGAATGGCGTCGGGTTTGGAGTTCAAGTCG
GTAGCCGACAGCGTTCTGTTTTTACGTGACAAAAGATGGGAAGAGGTCAGAGGTGCCCTG
ATGTCTGCTTTCAGTCCTGAAAAGGTGAACGAGATGGTTCCCCTCATCAGCCAAGCCTGC
GACCTTCTCCTGGCTCATTTAAAACGCTATGCGGAATCTGGGGACGCATTTGACATCCAG
AGGTGCTACTGCAATTACACCACAGATGTGGTTGCCAGCGTCCGCTTTGGCACCCCGGTG
GACTCCTGGCAGGCCCCTGAGGATCCCTTTGTGAAACACTGCAAGCGTTTCTTCGAATTC
TGCATCCCCAGACCTATCCTGGTTTTACTCTTATCATTTCCATCCATAATGGTCCCACTG
GCCCGGATTTTGCCCAATAAGAACCGAGACGAACTGAATGGCTTTTTTAACAAACTCATT
AGGAATGTGATTGCCTTGCGGGACCAGCAAGCTGCCGAAGAGAGGCGGAGAGACTTCCTC
CAAATGGTCCTGGATGCCCGACATTCTGCAAGTCCCATGGGCGTGCAAGACTTTGACATC
GTCAGAGACGTTTTCTCCTCTACTGGGTGCAAGCCGAACCCTTCCCGGCAACACCAGCCC
AGCCCTATGGCCAGGCCTTTGACTGTGGATGAGATTGTGGGCCAGGCCTTCATCTTCCTC
ATCGCTGGCTATGAAATCATCACCAACACACTTTCTTTTGCCACCTACCTACTGGCCACC
AACCCTGACTGCCAAGAGAAGCTTCTGAGAGAGGTAGACGTTTTTAAGGAGAAACACATG
GCCCCTGAGTTCTGCAGCCTCGAGGAAGGCCTGCCCTATCTGGACATGGTGATTGCAGAG
ACGCTGAGGATGTACCCGCCAGCTTTCAGATTCACACGGGAGGCAGCTCAGGACTGCGAG
GTGCTGGGGCAGCGCATCCCCGCAGGCGCTGTGCTAGAGATGGCCGGTGGGTGCCCTGCA
CCATGA
Target 1 GenBank Gene ID
Target 1 GeneCard ID TBXAS1 Link Image
Target 1 GenAtlas ID TBXAS1 Link Image
Target 1 HGNC ID HGNC:11609 Link Image
Target 1 Chromosome Location 7
Target 1 Locus 7q34-q35
Target 1 SNPs SNPJam Report Link Image
Target 1 General References Not Available
Target 1 Drug 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 Link Image]
  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 Link Image]
  3. 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 Link Image]
  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 Link Image]
Drug Target 2 [top]
Target 2 ID 835
Target 2 Name Thromboxane A2 receptor
Target 2 Synonyms
  1. Prostanoid TP receptor
  2. TXA2-R
Target 2 Gene Name TBXA2R
Target 2 Protein Sequence >Thromboxane A2 receptor 
MWPNGSSLGPCFRPTNITLEERRLIASPWFAASFCVVGLASNLLALSVLAGARQGGSHTR
SSFLTFLCGLVLTDFLGLLVTGTIVVSQHAALFEWHAVDPGCRLCRFMGVVMIFFGLSPL
LLGAAMASERYLGITRPFSRPAVASQRRAWATVGLVWAAALALGLLPLLGVGRYTVQYPG
SWCFLTLGAESGDVAFGLLFSMLGGLSVGLSFLLNTVSVATLCHVYHGQEAAQQRPRDSE
VEMMAQLLGIMVVASVCWLPLLVFIAQTVLRNPPAMSPAGQLSRTTEKELLIYLRVATWN
QILDPWVYILFRRAVLRRLQPRLSTRPRRVSLCGPAWSTVARSRLTATSASRVQAILVPQ
PPEQLGLQA
Target 2 Number of Residues 375
Target 2 Molecular Weight 40093
Target 2 Theoretical pI 10.31
Target 2 GO Classification
Function
icosanoid receptor activity
prostanoid receptor activity
thromboxane receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 2 General Function Involved in rhodopsin-like receptor activity
Target 2 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 activate a phosphatidylinositol-calcium second messenger system. In the kidney, the binding of TXA2 to glomerular TP receptors causes intense vasoconstriction
Target 2 Pathways Not Available
Target 2 Reactions Not Available
Target 2 Pfam Domain Function
Target 2 Signals
  • None
Target 2 Transmembrane Regions
  • 30-52
  • 67-87
  • 107-128
  • 150-172
  • 194-219
  • 247-270
  • 290-311
Target 2 Essentiality Non-Essential
Target 2 GenBank ID Protein 533326 Link Image
Target 2 UniProtKB/Swiss-Prot ID P21731 Link Image
Target 2 UniProtKB/Swiss-Prot Entry Name TA2R_HUMAN Link Image
Target 2 PDB ID Not Available
Target 2 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 2 Gene Sequence >1032 bp 
ATGTGGCCCAACGGCAGTTCCCTGGGGCCCTGTTTCCGGCCCACAAACATTACCCTGGAG
GAGAGACGGCTGATCGCCTCGCCCTGGTTCGCCGCCTCCTTCTGCGTGGTGGGCCTGGCC
TCCAACCTGCTGGCCCTGAGCGTGCTGGCGGGCGCGCGGCAGGGGGGTTCGCACACGCGC
TCCTCCTTCCTCACCTTCCTCTGCGGCCTCGTCCTCACCGACTTCCTGGGGCTGCTGGTG
ACCGGTACCATCGTGGTGTCCCAGCACGCCGCGCTCTTCGAGTGGCACGCCGTGGACCCT
GGCTGCCGTCTCTGTCGCTTCATGGGCGTCGTCATGATCTTCTTCGGCCTGTCCCCGCTG
CTGCTGGGGGCCGCCATGGCCTCAGAGCGCTACCTGGGTATCACCCGGCCCTTCTCGCGC
CCGGCGGTCGCCTCGCAGCGCCGCGCCTGGGCCACCGTGGGGCTGGTGTGGGCGGCCGCG
CTGGCGCTGGGCCTGCTGCCCCTGCTGGGCGTGGGTCGCTACACCGTGCAATACCCGGGG
TCCTGGTGCTTCCTGACGCTGGGCGCCGAGTCCGGGGACGTGGCCTTCGGGCTGCTCTTC
TCCATGCTGGGCGGCCTCTCGGTCGGGCTGTCCTTCCTGCTGAACACGGTCAGCGTGGCC
ACCCTGTGCCACGTCTACCACGGGCAGGAGGCGGCCCAGCAGCGTCCCCGGGACTCCGAG
GTGGAGATGATGGCTCAGCTCCTGGGGATCATGGTGGTGGCCAGCGTGTGTTGGCTGCCC
CTTCTGGTCTTCATTGCCCAGACAGTGCTGCGAAACCCGCCTGCCATGAGCCCCGCCGGG
CAGCTGTCCCGCACCACGGAGAAGGAGCTGCTCATCTACTTGCGCGTGGCCACCTGGAAC
CAGATCCTGGACCCCTGGGTGTATATCCTGTTCCGCCGCGCCGTGCTCCGGCGTCTCCAG
CCTCGCCTCAGCACCCGGCCCAGGTCGCTGTCCCTCCAGCCCCAGCTCACGCAGCGCTCC
GGGCTGCAGTAG
Target 2 GenBank Gene ID
Target 2 GeneCard ID TBXA2R Link Image
Target 2 GenAtlas ID TBXA2R Link Image
Target 2 HGNC ID HGNC:11608 Link Image
Target 2 Chromosome Location 19
Target 2 Locus 19p13.3
Target 2 SNPs SNPJam Report Link Image
Target 2 General References
  1. Hirata M, Hayashi Y, Ushikubi F, Yokota Y, Kageyama R, Nakanishi S, Narumiya S: Cloning and expression of cDNA for a human thromboxane A2 receptor. Nature. 1991 Feb 14;349(6310):617-20. [PubMed Link Image]
  2. Raychowdhury MK, Yukawa M, Collins LJ, McGrail SH, Kent KC, Ware JA: Alternative splicing produces a divergent cytoplasmic tail in the human endothelial thromboxane A2 receptor. J Biol Chem. 1995 Mar 24;270(12):7011. [PubMed Link Image]
  3. Hirata T, Kakizuka A, Ushikubi F, Fuse I, Okuma M, Narumiya S: Arg60 to Leu mutation of the human thromboxane A2 receptor in a dominantly inherited bleeding disorder. J Clin Invest. 1994 Oct;94(4):1662-7. [PubMed Link Image]
  4. D'Angelo DD, Davis MG, Ali S, Dorn GW 2nd: Cloning and pharmacologic characterization of a thromboxane A2 receptor from K562 (human chronic myelogenous leukemia) cells. J Pharmacol Exp Ther. 1994 Nov;271(2):1034-41. [PubMed Link Image]
  5. Raychowdhury MK, Yukawa M, Collins LJ, McGrail SH, Kent KC, Ware JA: Alternative splicing produces a divergent cytoplasmic tail in the human endothelial thromboxane A2 receptor. J Biol Chem. 1994 Jul 29;269(30):19256-61. [PubMed Link Image]
  6. Nusing RM, Hirata M, Kakizuka A, Eki T, Ozawa K, Narumiya S: Characterization and chromosomal mapping of the human thromboxane A2 receptor gene. J Biol Chem. 1993 Nov 25;268(33):25253-9. [PubMed Link Image]
  7. Funk CD, Furci L, Moran N, Fitzgerald GA: Point mutation in the seventh hydrophobic domain of the human thromboxane A2 receptor allows discrimination between agonist and antagonist binding sites. Mol Pharmacol. 1993 Nov;44(5):934-9. [PubMed Link Image]
Target 2 Drug References
  1. 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 Link Image]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed Link Image]
  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 Link Image]
  4. 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 Link Image]
  5. 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 Link Image]
  6. 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 Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.