ORBOFIBAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H23N5O4
Molecular Weight	361.3956
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)CCNC(=O)N[C@H]1CCN(C1=O)C2=CC=C(C=C2)C(N)=N

InChI

InChIKey=VJDOPFARMOLELX-ZDUSSCGKSA-N

InChI=1S/C17H23N5O4/c1-2-26-14(23)7-9-20-17(25)21-13-8-10-22(16(13)24)12-5-3-11(4-6-12)15(18)19/h3-6,13H,2,7-10H2,1H3,(H3,18,19)(H2,20,21,25)/t13-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17008974 | https://www.ncbi.nlm.nih.gov/pubmed/16442896 | Gresele Paolo , Born Gustav V. R, Patrono Carlo , Page Clive P., Antiplatelet Agents, retrieved from: https://books.google.ru/books?id=IXiJmHxiQzcC&pg=PA211&lpg=PA211&dq=ORBOFIBAN+discontinued&source=bl&ots=36YGroIDy9&sig=ACfU3U0NwkhiUhYMvIThhKkxUCjgc6X98Q&hl=ru&sa=X&ved=2ahUKEwidl42pi_DiAhVu16YKHdOGB3gQ6AEwBnoECAgQAQ#v=onepage&q=ORBOFIBAN%20discontinued&f=false

Orbofiban was developed as an orally active glycoprotein IIb/IIIa antagonist. By 2001, this drug had progressed to phase III clinical trials. Unfortunately, was found that orbofiban induced thrombocytopenia and thrombosis. In addition, despite no significant excess risk of intracranial hemorrhage, orbofiban was not effective in preventing ischemic stroke or transient ischemic attack. Besides, the use of this drug had led to an increase in mortality. Based on all these results further development of this drug was discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
G-protein beta3 subunit polymorphism and bleeding in the orbofiban in patients with unstable coronary syndromes-thrombolysis in myocardial infarction 16 trial.	2010-05	20096003
Risk factors for stroke after acute coronary syndromes in the Orbofiban in Patients with Unstable Coronary Syndromes--Thrombolysis In Myocardial Infarction (OPUS-TIMI) 16 study.	2006-02	16442896
Acute thrombocytopenia in patients treated with the oral glycoprotein IIb/IIIa inhibitors xemilofiban and orbofiban: evidence for an immune etiology.	2002-12	12529735
Xemilofiban/orbofiban: insight into drug development.	2001	11484066

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

Name

Type

Language

.BETA.-ALANINE, N-((((3S)-1-(4-(AMINOIMINOMETHYL)PHENYL)-2-OXO-3-PYRROLIDINYL)AMINO)CARBONYL)-, ETHYL ESTER

Preferred Name

English

ORBOFIBAN

Official Name

English

orbofiban [INN]

Common Name

English

Orbofiban [WHO-DD]

Common Name

English

Code System Code Type Description

PUBCHEM

178080