U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C18H17NO3
Molecular Weight 295.3325
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDOBUFEN

SMILES

CCC(C(O)=O)C1=CC=C(C=C1)N2CC3=C(C=CC=C3)C2=O

InChI

InChIKey=AYDXAULLCROVIT-UHFFFAOYSA-N
InChI=1S/C18H17NO3/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)

HIDE SMILES / InChI
Molecular Formula C18H17NO3
Molecular Weight 295.3325
Charge 0
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
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Phase III
665
Unknown

Approved Use

Unknown
Preventing
Approved
8583
Ibustrin

Approved Use

Unknown
Preventing
Approved
8583
Ibustrin

Approved Use

Unknown
Preventing
Approved
8583
Ibustrin

Approved Use

Unknown
Palliative
Approved
8583
Ibustrin

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
23 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11370020/
200 mg 2 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
INDOBUFEN, (R)- serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
17.8 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11370020/
200 mg 2 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
INDOBUFEN, (S)- serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
32.6 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3733275/
200 mg 2 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
INDOBUFEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
9.73 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1596290/
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
INDOBUFEN, (R)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
7.93 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1596290/
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
INDOBUFEN, (S)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
14.61 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/456404/
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
INDOBUFEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
10.24 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/456404/
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
INDOBUFEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2262 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11370020/
200 mg 2 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
INDOBUFEN, (R)- serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1309 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11370020/
200 mg 2 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
INDOBUFEN, (S)- serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
74.78 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/456404/
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
INDOBUFEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
64.67 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/456404/
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
INDOBUFEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.4 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11370020/
200 mg 2 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
INDOBUFEN, (R)- serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11370020/
200 mg 2 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
INDOBUFEN, (S)- serum
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
12.8 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/3733275/
200 mg 2 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
INDOBUFEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
8.68 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1596290/
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
INDOBUFEN, (R)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
6.21 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/1596290/
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
INDOBUFEN, (S)- plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
7.63 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/456404/
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
INDOBUFEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
6.77 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/456404/
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
INDOBUFEN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/12237835/
INDOBUFEN serum
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
400 mg 2 times / day multiple, oral
Highest studied dose
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9158644/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/9158644/
Other AEs: Stomach pain, Nausea...
Other AEs:
Stomach pain
Nausea
Vomiting
Bleeding (0.6%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/9158644/
AEs

AEs

AESignificanceDosePopulation
Nausea
400 mg 2 times / day multiple, oral
Highest studied dose
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9158644/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/9158644/
Stomach pain
400 mg 2 times / day multiple, oral
Highest studied dose
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9158644/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/9158644/
Vomiting
400 mg 2 times / day multiple, oral
Highest studied dose
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9158644/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/9158644/
Bleeding 0.6%
400 mg 2 times / day multiple, oral
Highest studied dose
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/9158644/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/9158644/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252
inhibitor
2438
inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C19
2057

CYP1A2
2153
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A2
2333
 inconclusive [IC50 27.5404 uM]
CYP2C9
2497
 inconclusive [IC50 30.9008 uM]
CYP3A4
2633
 no
CYP2D6
2546
 yes [IC50 15.4871 uM]
CYP2C19
2141
 yes [IC50 21.8761 uM]
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
PubMed

PubMed

TitleDatePubMed
Oral antiplatelet therapy in stroke prevention. Minireview.
2010-09
Antithrombotic therapy in cardiac embolism.
2010-08
A systematic review of clinical trials of pharmacological interventions for acute ischaemic stroke (1955-2008) that were completed, but not published in full.
2010-04-22
Emerging antiplatelet agents, differential pharmacology, and clinical utility.
2010
Modulatory effect of chiral nonsteroidal anti-inflammatory drugs on apoptosis of human neutrophils.
2008-02
Antiplatelet drugs in cardiological practice: established strategies and new developments.
2008
Clinical management of adult patients with a history of nonsteroidal anti-inflammatory drug-induced urticaria/angioedema: update.
2007-03-15
Upper gastrointestinal bleeding associated with antiplatelet drugs.
2006-01-15
Indobufen inhibits tissue factor in human monocytes through a thromboxane-mediated mechanism.
2006-01
[Recurrent hemoptysis following thienopyridines and amiodarone administration. therapeutic dilemma].
2005-08
Anticoagulants versus antiplatelet therapy for preventing stroke in patients with nonrheumatic atrial fibrillation and a history of stroke or transient ischemic attack.
2004-10-18
Atrial fibrillation and anticoagulation.
2004-10
Resolution of indobufen enantiomers by capillary zone electrophoresis. Pharmacokinetic studies of human serum.
2004-04-02
Endoscopic evaluation of the effects of indobufen and aspirin in healthy volunteers.
2004-03-05
[Stroke and Other Thromboembolic Complications of Atrial Fibrillation. Part III. Prevention With Other Antithrombotic Agents.].
2004
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].
2003-08-26
Protein binding of indobufen enantiomers: pharmacokinetics of free fraction-studies after single or multiple doses of rac-indobufen.
2002-10
Thromboembolic complications after total hip replacement.
2002
[Thromboembolism in non-rheumatic atrial fibrillation].
2001-09
[Guidelines for antithrombotic therapy in atrial fibrillation: what the Italian Hemostasis and Thrombosis Society thinks].
2001-09
Long term anticoagulation or antiplatelet treatment. Drug name was incorrect.
2001-07-28
Steady-state pharmacokinetics of indobufen enantiomers in patients with obliterative atherosclerosis.
2001-06
Systematic review of long term anticoagulation or antiplatelet treatment in patients with non-rheumatic atrial fibrillation.
2001-02-10
Indobufen: an updated review of its use in the management of atherothrombosis.
2001
A randomized trial comparing ticlopidine hydrochloride with indobufen for the prevention of stroke in high-risk patients (TISS Study). Ticlopidine Indobufen Stroke Study.
1997-01-01

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 Mon Mar 31 18:06:10 GMT 2025
Edited
by admin
on Mon Mar 31 18:06:10 GMT 2025
Record UNII
6T9949G4LZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
INDOBUFEN
INN   MART.   MI   WHO-DD  
INN  
Official Name English
IBUSTRIN
Preferred Name English
2-(4-(1-CARBOXYPROPYL)PHENYL)-1-ISOINDOLINONE
Systematic Name English
K-2930
Code English
Indobufen [WHO-DD]
Common Name English
BENZENEACETIC ACID, 4-(1,3-DIHYDRO-1-OXO-2H-ISOINDOL-2-YL)-.ALPHA.-ETHYL-, (±)-
Systematic Name English
INDOBUFEN [MI]
Common Name English
indobufen [INN]
Common Name English
(±)-2-(P-(1-OXO-2-ISOINDOLINYL)PHENYL)BUTYRIC ACID
Common Name English
INDOBUFEN [MART.]
Common Name English
K-3920
Code English
4-(1,3-DIHYDRO-1-OXO-2H-ISOINDOL-2-YL)-.ALPHA.-ETHYLBENZENEACETIC ACID
Systematic Name English
BENZENEACETIC ACID, 4-(1,3-DIHYDRO-1-OXO-2H-ISOINDOL-2-YL)-.ALPHA.-ETHYL-
Common Name English
1-OXO-2-(P-((.ALPHA.-ETHYL)CARBOXYMETHYL)PHENYL)ISOINDOLINE
Common Name English
Classification Tree Code System Code
WHO-ATC B01AC10
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
WHO-VATC QB01AC10
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
NCI_THESAURUS C257
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
Code System Code Type Description
DRUG BANK
DB12545
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
PRIMARY
MERCK INDEX
m6271
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C83800
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
PRIMARY
SMS_ID
100000088261
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
PRIMARY
CAS
36690-96-7
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
SUPERSEDED
FDA UNII
6T9949G4LZ
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
PRIMARY
MESH
C020371
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
PRIMARY
EPA CompTox
DTXSID7057789
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
PRIMARY
WIKIPEDIA
INDOBUFEN
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
PRIMARY
PUBCHEM
107641
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
PRIMARY
ChEMBL
CHEMBL1765292
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
PRIMARY
DRUG CENTRAL
1439
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
PRIMARY
RXCUI
27518
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
PRIMARY RxNorm
CAS
63610-08-2
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
PRIMARY
INN
4398
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
PRIMARY
EVMPD
SUB08176MIG
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
PRIMARY
ECHA (EC/EINECS)
264-364-4
Created by admin on Mon Mar 31 18:06:10 GMT 2025 , Edited by admin on Mon Mar 31 18:06:10 GMT 2025
PRIMARY
Related Record Type Details
Structure of INDOBUFEN, (S)-
ENANTIOMER -> RACEMATE
Structure of INDOBUFEN SODIUM
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of INDOBUFEN
ACTIVE MOIETY
NIH
NCATS
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