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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
Structure of PICOTAMIDE

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)

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

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
PubMed

PubMed

TitleDatePubMed
Dietary polyunsaturated fatty acid and antioxidant modulation of vascular dysfunction in the spontaneously hypertensive rat.
2001 Aug
NQ-Y15 inhibits the calcium mobilization by elevation of cyclic AMP in rat platelets.
2001 May
Evaluation of the effects of anti-thromboxane agents in platelet-vessel wall interaction.
2002 May 17
Thromboxane inhibition improves renal perfusion and excretory function in severe congestive heart failure.
2003 Jul 2
Picotamide in migraine aura prevention: a pilot study.
2004 Oct
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
Picotamide versus aspirin in diabetic patients with peripheral arterial disease: has David defeated Goliath?
2004 Oct
Migraine with aura from pathophysiology to treatment: therapeutic strategies.
2005 May
Picotamide reduced all-cause mortality more than aspirin in type 2 diabetes mellitus and peripheral arterial disease.
2005 May-Jun
Masterclass series in peripheral arterial disease. Antiplatelet therapy for peripheral arterial disease and claudication.
2006 Feb
Medical management of peripheral arterial disease.
2006 Jul 5
Treatment of aura: solving the puzzle.
2006 May
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
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
Antithrombotic treatment for peripheral arterial disease.
2007 Mar
Medical management and cardiovascular risk reduction in peripheral arterial disease.
2008 Fall
Antiplatelet therapy in diabetes: efficacy and limitations of current treatment strategies and future directions.
2009 Apr
Comparison of efficacy of antiplatelet treatments for patients with claudication. A meta-analysis.
2010 Apr
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
2009 World Congress on the Insulin Resistance Syndrome: cardiovascular disease concepts.
2010 Jul
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
Antiplatelet drugs--do we need new options? With a reappraisal of direct thromboxane inhibitors.
2010 May 7
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 Fri Dec 15 15:54:48 GMT 2023
Edited
by admin
on Fri Dec 15 15:54:48 GMT 2023
Record UNII
654G2VCI4Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PICOTAMIDE
MART.   MI   WHO-DD  
Common Name English
Picotamide [WHO-DD]
Common Name English
PICOTAMIDE [MART.]
Common Name English
1,3-BENZENEDICARBOXAMIDE, 4-METHOXY-N1,N3-BIS(3-PYRIDINYLMETHYL)-
Systematic Name English
1,3-BENZENEDICARBOXAMIDE, 4-METHOXY-N,N'-BIS(3-PYRIDINYLMETHYL)-
Systematic Name English
PICOTAMIDE [MI]
Common Name English
G-137
Code English
NSC-304384
Code English
Classification Tree Code System Code
WHO-VATC QB01AC03
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
WHO-ATC B01AC03
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
NCI_THESAURUS C1327
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
251-245-7
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
PRIMARY
CAS
32828-81-2
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
PRIMARY
MERCK INDEX
m8789
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
PRIMARY Merck Index
EVMPD
SUB14868MIG
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
PRIMARY
PUBCHEM
4814
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
PRIMARY
SMS_ID
100000092024
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
PRIMARY
NSC
304384
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID40186498
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
PRIMARY
FDA UNII
654G2VCI4Q
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
PRIMARY
WIKIPEDIA
PICOTAMIDE
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
PRIMARY
EVMPD
SUB127108
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
ALTERNATIVE
NCI_THESAURUS
C73157
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
PRIMARY
DRUG BANK
DB13327
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
PRIMARY
MESH
C011581
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
PRIMARY
ChEMBL
CHEMBL1257015
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
PRIMARY
DRUG CENTRAL
2161
Created by admin on Fri Dec 15 15:54:48 GMT 2023 , Edited by admin on Fri Dec 15 15:54:48 GMT 2023
PRIMARY
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ACTIVE MOIETY