INDOBUFEN SODIUM

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1965501

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

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase 89 Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1965501	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Atrial fibrillation 131 Sources: https://clinicaltrials.gov/ct2/show/NCT00244426	Preventing	Phase III 656	Unknown Approved Use Unknown
Cerebrovascular insufficiency 15 Sources: http://www.sukl.eu/modules/medication/detail.php?code=0047845&tab=info	Preventing	Approved 8429	Ibustrin Approved Use Unknown
Thrombophlebitis 3 Sources: http://www.sukl.eu/modules/medication/detail.php?code=0047845&tab=info	Preventing	Approved 8429	Ibustrin Approved Use Unknown
Deep vein thrombosis 12 Sources: http://www.sukl.eu/modules/medication/detail.php?code=0047845&tab=info	Preventing	Approved 8429	Ibustrin Approved Use Unknown
Diabetes mellitus 91 Sources: http://www.sukl.eu/modules/medication/detail.php?code=0047845&tab=info	Palliative	Approved 8429	Ibustrin Approved Use Unknown

PubMed

Title	Date	PubMed
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	9127122
Indobufen: an updated review of its use in the management of atherothrombosis.	2001	11392445
Systematic review of long term anticoagulation or antiplatelet treatment in patients with non-rheumatic atrial fibrillation.	2001 Feb 10	11159653
Long term anticoagulation or antiplatelet treatment. Drug name was incorrect.	2001 Jul 28	11496889
Steady-state pharmacokinetics of indobufen enantiomers in patients with obliterative atherosclerosis.	2001 Jun	11370020
[Thromboembolism in non-rheumatic atrial fibrillation].	2001 Sep	11759619
[Guidelines for antithrombotic therapy in atrial fibrillation: what the Italian Hemostasis and Thrombosis Society thinks].	2001 Sep	11759618
Thromboembolic complications after total hip replacement.	2002	11954849
Protein binding of indobufen enantiomers: pharmacokinetics of free fraction-studies after single or multiple doses of rac-indobufen.	2002 Oct	12237835
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	12939169
[Stroke and Other Thromboembolic Complications of Atrial Fibrillation. Part III. Prevention With Other Antithrombotic Agents.].	2004	15477780
Resolution of indobufen enantiomers by capillary zone electrophoresis. Pharmacokinetic studies of human serum.	2004 Apr 2	15065799
Endoscopic evaluation of the effects of indobufen and aspirin in healthy volunteers.	2004 Mar-Apr	14999361
Atrial fibrillation and anticoagulation.	2004 Oct	16008178
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	15494992
[Recurrent hemoptysis following thienopyridines and amiodarone administration. therapeutic dilemma].	2005 Aug	16808316
Indobufen inhibits tissue factor in human monocytes through a thromboxane-mediated mechanism.	2006 Jan	16154551
Upper gastrointestinal bleeding associated with antiplatelet drugs.	2006 Jan 15	16393302
Clinical management of adult patients with a history of nonsteroidal anti-inflammatory drug-induced urticaria/angioedema: update.	2007 Mar 15	20525150
Antiplatelet drugs in cardiological practice: established strategies and new developments.	2008	18827913
Modulatory effect of chiral nonsteroidal anti-inflammatory drugs on apoptosis of human neutrophils.	2008 Feb	18092300
Emerging antiplatelet agents, differential pharmacology, and clinical utility.	2010	22282687
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	20412562
Antithrombotic therapy in cardiac embolism.	2010 Aug	21804782
Oral antiplatelet therapy in stroke prevention. Minireview.	2010 Sep	21048805

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).

Name

Type

Language

INDOBUFEN SODIUM

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