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

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 of ORBOFIBAN

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

Molecular Formula C17H23N5O4
Molecular Weight 361.3956
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Acute thrombocytopenia in patients treated with the oral glycoprotein IIb/IIIa inhibitors xemilofiban and orbofiban: evidence for an immune etiology.
2002 Dec

Sample Use Guides

Unknown
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:31:29 GMT 2023
Edited
by admin
on Sat Dec 16 16:31:29 GMT 2023
Record UNII
FGJ53JS7PT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ORBOFIBAN
INN   WHO-DD  
INN  
Official Name English
.BETA.-ALANINE, N-((((3S)-1-(4-(AMINOIMINOMETHYL)PHENYL)-2-OXO-3-PYRROLIDINYL)AMINO)CARBONYL)-, ETHYL ESTER
Common Name English
orbofiban [INN]
Common Name English
Orbofiban [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
178080
Created by admin on Sat Dec 16 16:31:30 GMT 2023 , Edited by admin on Sat Dec 16 16:31:30 GMT 2023
PRIMARY
FDA UNII
FGJ53JS7PT
Created by admin on Sat Dec 16 16:31:30 GMT 2023 , Edited by admin on Sat Dec 16 16:31:30 GMT 2023
PRIMARY
CAS
163250-90-6
Created by admin on Sat Dec 16 16:31:30 GMT 2023 , Edited by admin on Sat Dec 16 16:31:30 GMT 2023
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ChEMBL
CHEMBL64706
Created by admin on Sat Dec 16 16:31:30 GMT 2023 , Edited by admin on Sat Dec 16 16:31:30 GMT 2023
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EPA CompTox
DTXSID20167543
Created by admin on Sat Dec 16 16:31:30 GMT 2023 , Edited by admin on Sat Dec 16 16:31:30 GMT 2023
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EVMPD
SUB09455MIG
Created by admin on Sat Dec 16 16:31:30 GMT 2023 , Edited by admin on Sat Dec 16 16:31:30 GMT 2023
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INN
7508
Created by admin on Sat Dec 16 16:31:30 GMT 2023 , Edited by admin on Sat Dec 16 16:31:30 GMT 2023
PRIMARY
NCI_THESAURUS
C170261
Created by admin on Sat Dec 16 16:31:30 GMT 2023 , Edited by admin on Sat Dec 16 16:31:30 GMT 2023
PRIMARY
MESH
C120234
Created by admin on Sat Dec 16 16:31:30 GMT 2023 , Edited by admin on Sat Dec 16 16:31:30 GMT 2023
PRIMARY
SMS_ID
100000083344
Created by admin on Sat Dec 16 16:31:30 GMT 2023 , Edited by admin on Sat Dec 16 16:31:30 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG