Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H20N4O3.H2O |
| Molecular Weight | 394.4238 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.COC1=C(C=C(C=C1)C(=O)NCC2=CN=CC=C2)C(=O)NCC3=CN=CC=C3
InChI
InChIKey=ICYQAMNVLLHURR-UHFFFAOYSA-N
InChI=1S/C21H20N4O3.H2O/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);1H2
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C21H20N4O3 |
| Molecular Weight | 376.4085 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|---|
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 |
|---|---|---|---|---|
| Primary | Plactidil Approved UseUnknown |
|||
| Primary | Plactidil Approved UseUnknown |
|||
| Primary | Plactidil Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.02 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1400771/ |
300 mg single, oral dose: 300 mg route of administration: Oral experiment type: SINGLE co-administered: |
PICOTAMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
300 mg 3 times / day multiple, oral Studied dose Dose: 300 mg, 3 times / day Route: oral Route: multiple Dose: 300 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Gastrointestinal disorder... AEs leading to discontinuation/dose reduction: Gastrointestinal disorder Sources: |
300 mg 3 times / day multiple, oral Studied dose Dose: 300 mg, 3 times / day Route: oral Route: multiple Dose: 300 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Gastrointestinal disorder | Disc. AE | 300 mg 3 times / day multiple, oral Studied dose Dose: 300 mg, 3 times / day Route: oral Route: multiple Dose: 300 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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. | 2010-12 |
|
| 2009 World Congress on the Insulin Resistance Syndrome: cardiovascular disease concepts. | 2010-07 |
|
| Antiplatelet drugs--do we need new options? With a reappraisal of direct thromboxane inhibitors. | 2010-05-07 |
|
| Comparison of efficacy of antiplatelet treatments for patients with claudication. A meta-analysis. | 2010-04 |
|
| The effect of non-steroidal anti-inflammatory agents on behavioural changes and cytokine production following systemic inflammation: Implications for a role of COX-1. | 2010-03 |
|
| Antiplatelet therapy in diabetes: efficacy and limitations of current treatment strategies and future directions. | 2009-04 |
|
| Medical management and cardiovascular risk reduction in peripheral arterial disease. | 2008 |
|
| Antithrombotic treatment for peripheral arterial disease. | 2007-03 |
|
| A review of picotamide in the reduction of cardiovascular events in diabetic patients. | 2007 |
|
| Approaches to prevention of cardiovascular complications and events in diabetes mellitus. | 2007 |
|
| Medical management of peripheral arterial disease. | 2006-07-05 |
|
| Treatment of aura: solving the puzzle. | 2006-05 |
|
| 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. | 2006-05 |
|
| Masterclass series in peripheral arterial disease. Antiplatelet therapy for peripheral arterial disease and claudication. | 2006-02 |
|
| Picotamide reduced all-cause mortality more than aspirin in type 2 diabetes mellitus and peripheral arterial disease. | 2005-05-03 |
|
| Migraine with aura from pathophysiology to treatment: therapeutic strategies. | 2005-05 |
|
| Picotamide in migraine aura prevention: a pilot study. | 2004-10 |
|
| Picotamide, a combined inhibitor of thromboxane A2 synthase and receptor, reduces 2-year mortality in diabetics with peripheral arterial disease: the DAVID study. | 2004-10 |
|
| Picotamide versus aspirin in diabetic patients with peripheral arterial disease: has David defeated Goliath? | 2004-10 |
|
| Thromboxane inhibition improves renal perfusion and excretory function in severe congestive heart failure. | 2003-07-02 |
|
| Evaluation of the effects of anti-thromboxane agents in platelet-vessel wall interaction. | 2002-05-17 |
|
| Dietary polyunsaturated fatty acid and antioxidant modulation of vascular dysfunction in the spontaneously hypertensive rat. | 2001-08 |
|
| NQ-Y15 inhibits the calcium mobilization by elevation of cyclic AMP in rat platelets. | 2001-05 |
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.
| Substance Class |
Chemical
Created
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| Record UNII |
643HY5UHKS
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| Record Status |
Validated (UNII)
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ANHYDROUS->SOLVATE |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |
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