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Details

Stereochemistry RACEMIC
Molecular Formula C18H16NO3.Na
Molecular Weight 317.3143
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDOBUFEN SODIUM

SMILES

[Na+].CCC(C([O-])=O)C1=CC=C(C=C1)N2CC3=CC=CC=C3C2=O

InChI

InChIKey=MEWDXXPKUBKKJO-UHFFFAOYSA-M
InChI=1S/C18H17NO3.Na/c1-2-15(18(21)22)12-7-9-14(10-8-12)19-11-13-5-3-4-6-16(13)17(19)20;/h3-10,15H,2,11H2,1H3,(H,21,22);/q;+1/p-1

HIDE SMILES / InChI
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C18H16NO3
Molecular Weight 294.3245
Charge -1
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Indobufen inhibits platelet aggregation by reversibly inhibiting the platelet cyclooxygenase enzyme thereby suppressing thromboxane synthesis. Indobufen under brand name ibustrin is used in Italy for the following conditions: cerebrovascular insufficiency, atherosclerosis of peripheral and cerebral vessels, thrombophlebitis, deep vein thrombosis, and diabetes mellitus. In addition, this drug has been investigated in the phase II clinical trial for the prevention of thromboembolic events in patients with nonrheumatic atrial fibrillation. After oral administration, it is quickly and completely absorbed.

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Phase III
656
Unknown

Approved Use

Unknown
Preventing
Approved
8429
Ibustrin

Approved Use

Unknown
Preventing
Approved
8429
Ibustrin

Approved Use

Unknown
Preventing
Approved
8429
Ibustrin

Approved Use

Unknown
Palliative
Approved
8429
Ibustrin

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A randomized trial comparing ticlopidine hydrochloride with indobufen for the prevention of stroke in high-risk patients (TISS Study). Ticlopidine Indobufen Stroke Study.
1997 Jan-Feb
Indobufen: an updated review of its use in the management of atherothrombosis.
2001
Systematic review of long term anticoagulation or antiplatelet treatment in patients with non-rheumatic atrial fibrillation.
2001 Feb 10
Long term anticoagulation or antiplatelet treatment. Drug name was incorrect.
2001 Jul 28
[Thromboembolism in non-rheumatic atrial fibrillation].
2001 Sep
[Guidelines for antithrombotic therapy in atrial fibrillation: what the Italian Hemostasis and Thrombosis Society thinks].
2001 Sep
Thromboembolic complications after total hip replacement.
2002
Protein binding of indobufen enantiomers: pharmacokinetics of free fraction-studies after single or multiple doses of rac-indobufen.
2002 Oct
Protocol for Birmingham Atrial Fibrillation Treatment of the Aged study (BAFTA): a randomised controlled trial of warfarin versus aspirin for stroke prevention in the management of atrial fibrillation in an elderly primary care population [ISRCTN89345269].
2003 Aug 26
[Stroke and Other Thromboembolic Complications of Atrial Fibrillation. Part III. Prevention With Other Antithrombotic Agents.].
2004
Resolution of indobufen enantiomers by capillary zone electrophoresis. Pharmacokinetic studies of human serum.
2004 Apr 2
Endoscopic evaluation of the effects of indobufen and aspirin in healthy volunteers.
2004 Mar-Apr
Atrial fibrillation and anticoagulation.
2004 Oct
Anticoagulants versus antiplatelet therapy for preventing stroke in patients with nonrheumatic atrial fibrillation and a history of stroke or transient ischemic attack.
2004 Oct 18
[Recurrent hemoptysis following thienopyridines and amiodarone administration. therapeutic dilemma].
2005 Aug
Indobufen inhibits tissue factor in human monocytes through a thromboxane-mediated mechanism.
2006 Jan
Upper gastrointestinal bleeding associated with antiplatelet drugs.
2006 Jan 15
Clinical management of adult patients with a history of nonsteroidal anti-inflammatory drug-induced urticaria/angioedema: update.
2007 Mar 15
Antiplatelet drugs in cardiological practice: established strategies and new developments.
2008
Modulatory effect of chiral nonsteroidal anti-inflammatory drugs on apoptosis of human neutrophils.
2008 Feb
Emerging antiplatelet agents, differential pharmacology, and clinical utility.
2010
A systematic review of clinical trials of pharmacological interventions for acute ischaemic stroke (1955-2008) that were completed, but not published in full.
2010 Apr 22
Antithrombotic therapy in cardiac embolism.
2010 Aug
Oral antiplatelet therapy in stroke prevention. Minireview.
2010 Sep

Sample Use Guides

In Vivo Use Guide
indobufen capsules 100 and 200 mg
Route of Administration: Oral
In Vitro Use Guide
At low concentrations (10 microM), indobufen completely inhibited secondary platelet aggregation, the release reaction and TxB2 production stimulated by ADP, epinephrine and low concentrations of platelet-activating factor (PAF acether). Higher concentrations of indobufen (100 microM) completely inhibited TxB2 production, platelet aggregation and ATP release induced by arachidonic acid (1 mM) or collagen (2 micrograms/ml). The inhibitory effect was partially overcome by higher concentrations of arachidonic acid (2 mM).
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:16:15 UTC 2023
Edited
by admin
on Fri Dec 15 16:16:15 UTC 2023
Record UNII
Y7A7KH8465
Record Status Validated (UNII)
Record Version
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Name Type Language
INDOBUFEN SODIUM
WHO-DD  
Common Name English
(±)-2-(P-(1-OXO-2-ISOINDOLINYL)PHENYL)BUTYRIC ACID, SODIUM SALT
Common Name English
BENZENEACETIC ACID, 4-(1,3-DIHYDRO-1-OXO-2H-ISOINDOL-2-YL)-.ALPHA.-ETHYL-, SODIUM SALT (1:1)
Common Name English
Indobufen sodium [WHO-DD]
Common Name English
BENZENEACETIC ACID, 4-(1,3-DIHYDRO-1-OXO-2H-ISOINDOL-2-YL)-.ALPHA.-ETHYL-, SODIUM SALT
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C257
Created by admin on Fri Dec 15 16:16:15 UTC 2023 , Edited by admin on Fri Dec 15 16:16:15 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C96751
Created by admin on Fri Dec 15 16:16:15 UTC 2023 , Edited by admin on Fri Dec 15 16:16:15 UTC 2023
PRIMARY
EVMPD
SUB02674MIG
Created by admin on Fri Dec 15 16:16:15 UTC 2023 , Edited by admin on Fri Dec 15 16:16:15 UTC 2023
PRIMARY
CAS
94135-04-3
Created by admin on Fri Dec 15 16:16:15 UTC 2023 , Edited by admin on Fri Dec 15 16:16:15 UTC 2023
PRIMARY
ECHA (EC/EINECS)
302-872-0
Created by admin on Fri Dec 15 16:16:15 UTC 2023 , Edited by admin on Fri Dec 15 16:16:15 UTC 2023
PRIMARY
PUBCHEM
91668149
Created by admin on Fri Dec 15 16:16:15 UTC 2023 , Edited by admin on Fri Dec 15 16:16:15 UTC 2023
PRIMARY
EPA CompTox
DTXSID50916344
Created by admin on Fri Dec 15 16:16:15 UTC 2023 , Edited by admin on Fri Dec 15 16:16:15 UTC 2023
PRIMARY
SMS_ID
100000086405
Created by admin on Fri Dec 15 16:16:15 UTC 2023 , Edited by admin on Fri Dec 15 16:16:15 UTC 2023
PRIMARY
FDA UNII
Y7A7KH8465
Created by admin on Fri Dec 15 16:16:15 UTC 2023 , Edited by admin on Fri Dec 15 16:16:15 UTC 2023
PRIMARY
Related Record Type Details
Structure of INDOBUFEN
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of INDOBUFEN
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