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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H20N4O3.C4H6O6
Molecular Weight 526.4953
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PICOTAMIDE TARTRATE

SMILES

O[C@H]([C@@H](O)C(O)=O)C(O)=O.COC1=CC=C(C=C1C(=O)NCC2=CC=CN=C2)C(=O)NCC3=CN=CC=C3

InChI

InChIKey=XOHPDDYEORLRNT-LREBCSMRSA-N
InChI=1S/C21H20N4O3.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h2-12H,13-14H2,1H3,(H,24,26)(H,25,27);1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.1/s1

HIDE SMILES / InChI

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

Molecular Formula C4H6O6
Molecular Weight 150.0868
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Sources: Chimica Therapeutica (1971), 6, (3), 203-7.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.15 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Plactidil

Approved Use

Unknown
Primary
Plactidil

Approved Use

Unknown
Primary
Plactidil

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.02 μg/mL
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

Doses

DosePopulationAdverse 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

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
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

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
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
by admin
on Mon Mar 31 23:33:29 GMT 2025
Edited
by admin
on Mon Mar 31 23:33:29 GMT 2025
Record UNII
7PLJ5N16ZY
Record Status Validated (UNII)
Record Version
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Name Type Language
1,3-BENZENEDICARBOXAMIDE, 4-METHOXY-N,N'-BIS(3-PYRIDINYLMETHYL)-, (R-(R*,R*))-2,3-DIHYDROXYBUTANEDIOATE
Preferred Name English
PICOTAMIDE TARTRATE
Common Name English
1,3-BENZENEDICARBOXAMIDE, 4-METHOXY-N,N'-BIS(3-PYRIDINYLMETHYL)-, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE
Systematic Name English
Code System Code Type Description
FDA UNII
7PLJ5N16ZY
Created by admin on Mon Mar 31 23:33:29 GMT 2025 , Edited by admin on Mon Mar 31 23:33:29 GMT 2025
PRIMARY
PUBCHEM
92135774
Created by admin on Mon Mar 31 23:33:29 GMT 2025 , Edited by admin on Mon Mar 31 23:33:29 GMT 2025
PRIMARY
CAS
86247-87-2
Created by admin on Mon Mar 31 23:33:29 GMT 2025 , Edited by admin on Mon Mar 31 23:33:29 GMT 2025
NON-SPECIFIC STOICHIOMETRY
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