Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H20N4O3 |
Molecular Weight | 376.4085 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C(C=C(C=C1)C(=O)NCC2=CN=CC=C2)C(=O)NCC3=CC=CN=C3
InChI
InChIKey=KYWCWBXGRWWINE-UHFFFAOYSA-N
InChI=1S/C21H20N4O3/c1-28-19-7-6-17(20(26)24-13-15-4-2-8-22-11-15)10-18(19)21(27)25-14-16-5-3-9-23-12-16/h2-12H,13-14H2,1H3,(H,24,26)(H,25,27)
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24049147Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24298905 | https://www.ncbi.nlm.nih.gov/pubmed/15549555 | https://www.ncbi.nlm.nih.gov/pubmed/10367219 | https://www.ncbi.nlm.nih.gov/pubmed/9704127
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24049147
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24298905 | https://www.ncbi.nlm.nih.gov/pubmed/15549555 | https://www.ncbi.nlm.nih.gov/pubmed/10367219 | https://www.ncbi.nlm.nih.gov/pubmed/9704127
Picotamide (brand name Plactidil) is a platelet aggregation inhibitor. It works as a thromboxane synthase inhibitor and a thromboxane receptor inhibitor, the latter by modifying cellular responses to activation of the thromboxane receptor. Picotamide is licensed in Italy for the treatment of clinical arterial thrombosis and peripheral artery disease.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1835 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2552606 |
0.15 mM [IC50] | ||
Target ID: CHEMBL2069 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2552606 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Plactidil Approved UseUnknown |
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Primary | Plactidil Approved UseUnknown |
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Primary | Plactidil Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Dietary polyunsaturated fatty acid and antioxidant modulation of vascular dysfunction in the spontaneously hypertensive rat. | 2001 Aug |
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NQ-Y15 inhibits the calcium mobilization by elevation of cyclic AMP in rat platelets. | 2001 May |
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Evaluation of the effects of anti-thromboxane agents in platelet-vessel wall interaction. | 2002 May 17 |
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Thromboxane inhibition improves renal perfusion and excretory function in severe congestive heart failure. | 2003 Jul 2 |
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Picotamide in migraine aura prevention: a pilot study. | 2004 Oct |
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Picotamide, a combined inhibitor of thromboxane A2 synthase and receptor, reduces 2-year mortality in diabetics with peripheral arterial disease: the DAVID study. | 2004 Oct |
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Picotamide versus aspirin in diabetic patients with peripheral arterial disease: has David defeated Goliath? | 2004 Oct |
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Migraine with aura from pathophysiology to treatment: therapeutic strategies. | 2005 May |
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Picotamide reduced all-cause mortality more than aspirin in type 2 diabetes mellitus and peripheral arterial disease. | 2005 May-Jun |
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Masterclass series in peripheral arterial disease. Antiplatelet therapy for peripheral arterial disease and claudication. | 2006 Feb |
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Medical management of peripheral arterial disease. | 2006 Jul 5 |
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Treatment of aura: solving the puzzle. | 2006 May |
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Pharmacological characterization of 2NTX-99 [4-methoxy-N1-(4-trans-nitrooxycyclohexyl)-N3-(3-pyridinylmethyl)-1,3-benzenedicarboxamide], a potential antiatherothrombotic agent with antithromboxane and nitric oxide donor activity in platelet and vascular preparations. | 2006 May |
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A review of picotamide in the reduction of cardiovascular events in diabetic patients. | 2007 |
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Approaches to prevention of cardiovascular complications and events in diabetes mellitus. | 2007 |
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Antithrombotic treatment for peripheral arterial disease. | 2007 Mar |
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Medical management and cardiovascular risk reduction in peripheral arterial disease. | 2008 Fall |
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Antiplatelet therapy in diabetes: efficacy and limitations of current treatment strategies and future directions. | 2009 Apr |
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Comparison of efficacy of antiplatelet treatments for patients with claudication. A meta-analysis. | 2010 Apr |
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8-isoprostane F2α up-regulates the expression of type 5 phosphodiesterase in cavernosal vascular smooth muscle cells: inhibition with sildenafil, iloprost, nitric oxide and picotamide. | 2010 Dec |
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2009 World Congress on the Insulin Resistance Syndrome: cardiovascular disease concepts. | 2010 Jul |
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The effect of non-steroidal anti-inflammatory agents on behavioural changes and cytokine production following systemic inflammation: Implications for a role of COX-1. | 2010 Mar |
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Antiplatelet drugs--do we need new options? With a reappraisal of direct thromboxane inhibitors. | 2010 May 7 |
Patents
Sample Use Guides
In attack therapy from 900 to 1200 mg / day in three oral administrations.
In maintenance therapy from 300 to 600 mg / day in one or more oral administration.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24049147
Prostate strips (6 x 3 x 3 mm) were mounted in 10-ml aerated (95% O2-5% CO2) tissue baths (Föhr Medical Instruments, Seeheim, Germany), containing Krebs-Henseleit solution (37°C, pH 7.4). Preparations were stretched to 0.5 g and left to equilibrate for 45 min. In the initial phase of the equilibration period, spontaneous decreases in tone are usually observed. Therefore, tension was adjusted three times during the equilibration period, until a stable resting tone (0.5 g) was attained. After the equilibration period, maximum contraction induced by 80 mM KCl (Krebs-Henseleit solution where NaCl was exchanged by KCl) was assessed. Subsequently, chambers were washed three times with Krebs-Henseleit solution for a total of 30 min. Cumulative concentration response curves for U46619, norepinephrine, or phenylephrine were created after addition of TXA2-R antagonists (Picotamide 0.1-30mkM) or solvent [dimethylsulfoxide (DMSO)]. Frequency response curves induced by electric field stimulation (EFS) were created before and after addition of antagonists or DMSO. Antagonists or DMSO were applied 45 min before concentration or frequency response curves.
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WHO-VATC |
QB01AC03
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B01AC03
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NCI_THESAURUS |
C1327
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32828-81-2
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m8789
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SUB14868MIG
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4814
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100000092024
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304384
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DTXSID40186498
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PICOTAMIDE
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SUB127108
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C73157
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DB13327
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C011581
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CHEMBL1257015
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2161
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ACTIVE MOIETY
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