INDOBUFEN, (S)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H17NO3
Molecular Weight	295.3325
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@H](C(O)=O)C1=CC=C(C=C1)N2CC3=C(C=CC=C3)C2=O

InChI

InChIKey=AYDXAULLCROVIT-HNNXBMFYSA-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)/t15-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C18H17NO3
Molecular Weight	295.3325
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7996488 | https://www.ncbi.nlm.nih.gov/pubmed/1382938 | https://www.ncbi.nlm.nih.gov/pubmed/1965501 | http://www.mims.com/india/drug/info/indobufen?type=full&mtype=generic

Indobufen is an inhibitor of platelet aggregation which acts by reversibly inhibiting the platelet cyclo-oxygenase enzyme. Indobufen under brand name Ibustrin is used 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. Racemic indobufen caused a dose-dependent inhibition of TXB2 and PGE2 production (IC50: 0.53 /- 0.06 and 0.34 /- 0.02 ug/ml, respectively). S-Indobufen was approximately 2-fold more potent than the racemate in inhibiting the synthesis of cyclooxygenase products. R-Indobufen affected the same enzyme but only at considerably higher concentrations (IC50: 53 /- 8 ug/ml). Serum LTB4 concentrations were significantly reduced only at indobufen concentrations greater than 50 ug/ml. In conclusion, indobufen is a selective inhibitor of the cyclooxygenase activity of platelet PGG/H synthase in a concentration range corresponding to the therapeutic plasma levels in man. This inhibitory effect is largely due to the S isomer of the drug.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-1 131 Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7996488 \| https://www.ncbi.nlm.nih.gov/pubmed/1965501	Inhibitor 8504		0.64 µM [IC50]
Cyclooxygenase-2 201 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7996488 \| https://www.ncbi.nlm.nih.gov/pubmed/1965501	Inhibitor 8504		14.9 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Thromboembolic disorders 1 Sources: http://www.mims.com/india/drug/info/indobufen?type=full&mtype=generic	Preventing	Approved 8583	Indobufen Approved Use Thromboembolic disorders
Cerebrovascular insufficiency 15 Sources: http://www.sukl.eu/modules/medication/detail.php?code=0047845&tab=info	Preventing	Approved 8583	Ibustrin Approved Use IHD, cerebrovascular insufficiency, atherosclerosis of peripheral and cerebral vessels, thrombophlebitis, deep vein thrombosis, diabetes mellitus.
Atrial fibrillation 131 Sources: https://clinicaltrials.gov/ct2/show/NCT00244426	Preventing	Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
7.93 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1596290/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: (-)-Indobufen	(-)-Indobufen	INDOBUFEN, (S)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
12.5 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10602265	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: (-)-Indobufen	(-)-Indobufen	INDOBUFEN, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
9.4 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10602265	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: (-)-Indobufen	(-)-Indobufen	INDOBUFEN, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
12.2 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10602265	100 mg single, intramuscular dose: 100 mg route of administration: Intramuscular experiment type: SINGLE co-administered: (-)-Indobufen	(-)-Indobufen	INDOBUFEN, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
11.4 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10602265	100 mg single, intramuscular dose: 100 mg route of administration: Intramuscular experiment type: SINGLE co-administered: (-)-Indobufen	(-)-Indobufen	INDOBUFEN, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
71.7 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10602265	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: (-)-Indobufen	(-)-Indobufen	INDOBUFEN, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
78.1 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10602265	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: (-)-Indobufen	(-)-Indobufen	INDOBUFEN, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
65.2 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10602265	100 mg single, intramuscular dose: 100 mg route of administration: Intramuscular experiment type: SINGLE co-administered: (-)-Indobufen	(-)-Indobufen	INDOBUFEN, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
59 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10602265	100 mg single, intramuscular dose: 100 mg route of administration: Intramuscular experiment type: SINGLE co-administered: (-)-Indobufen	(-)-Indobufen	INDOBUFEN, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.21 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1596290/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: (-)-Indobufen	(-)-Indobufen	INDOBUFEN, (S)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10602265	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: (-)-Indobufen	(-)-Indobufen	INDOBUFEN, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10602265	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: (-)-Indobufen	(-)-Indobufen	INDOBUFEN, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10602265	100 mg single, intramuscular dose: 100 mg route of administration: Intramuscular experiment type: SINGLE co-administered: (-)-Indobufen	(-)-Indobufen	INDOBUFEN, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10602265	100 mg single, intramuscular dose: 100 mg route of administration: Intramuscular experiment type: SINGLE co-administered: (-)-Indobufen	(-)-Indobufen	INDOBUFEN, (S)- serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12237835/	100 mg 2 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: (-)-Indobufen	(-)-Indobufen	INDOBUFEN, (S)- serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

PubMed

Title	Date	PubMed
Biochemical and pharmacological characterization of the cyclooxygenase activity of human blood prostaglandin endoperoxide synthases.	1994-12	7996488
Excretion balance and urinary metabolites of the S-enantiomer of indobufen in rats and mice.	1993-10-19	8240403
The dispositional enantioselectivity of indobufen in man.	1992-05-08	1596290
The dispositional enantioselectivity of indobufen in rat and mouse.	1990-10-15	2242009

Sample Use Guides

In Vivo Use Guide

After fasting overnight, 12 healthy male volunteers (aged 23-39 years, body wt 56--87 kg) received a single dose of 100 mg of S-indobufen.

Route of Administration: Oral

In Vitro Use Guide

S-indobufen inhibited TXB2 and PGE2 production in A23187-stimulated human whole blood with an IC50 of 0.28 and 0.21 ug/ml. S-indobufen significantly reduced LTB4 production only at concentrations higher than 10 ug/ml (IC50: 100 ug/ml).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:38:23 GMT 2025` Edited by `admin` on `Mon Mar 31 18:38:23 GMT 2025`
Record UNII	58LEO57GJB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

INDOBUFEN, (S)-

Common Name

English

(+)-2-(P-(1-OXO-2-ISOINDOLINYL)PHENYL)BUTYRIC ACID

Preferred Name

English

(S)-(+)-INDOBUFEN

Common Name

English

BENZENEACETIC ACID, 4-(1,3-DIHYDRO-1-OXO-2H-ISOINDOL-2-YL)-.ALPHA.-ETHYL-, (S)-

Common Name

English

(S)-INDOBUFEN

Common Name

English

INDOBUFEN, D-

Common Name

English

(S)-2-(P-(1-OXO-2-ISOINDOLINYL)PHENYL)BUTYRIC ACID

Common Name

English

S-INDOBUFEN

Common Name

English

D-INDOBUFEN

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C257