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

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H22N4O4
Molecular Weight 358.3917
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of XEMILOFIBAN

SMILES

CCOC(=O)C[C@H](NC(=O)CCC(=O)NC1=CC=C(C=C1)C(N)=N)C#C

InChI

InChIKey=ZHCINJQZDFCSEL-CYBMUJFWSA-N
InChI=1S/C18H22N4O4/c1-3-13(11-17(25)26-4-2)21-15(23)9-10-16(24)22-14-7-5-12(6-8-14)18(19)20/h1,5-8,13H,4,9-11H2,2H3,(H3,19,20)(H,21,23)(H,22,24)/t13-/m1/s1

HIDE SMILES / InChI
Xemilofiban [SC 54684, SC 54684A (HCl), xemlofiban], an orally active antiplatelet agent, is a glycoprotein IIb/IIIa receptor antagonist. This drug was in a phase III clinical trial in the US and Europe for the treatment of thrombosis in patients with unstable angina pectoris and acute myocardial infarction undergoing angioplasty. Because of insufficient evidence of efficacy and concerns about safety over this long of a period of treatment, these trials didn’t get the market approval. In Japan, Sankyo discontinued the development of xemilofiban for thrombosis at phase II following Searle's decision to drop the project.

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
Usefulness of proteinuria as a prognostic marker of mortality and cardiovascular events among patients undergoing percutaneous coronary intervention (data from the Evaluation of Oral Xemilofiban in Controlling Thrombotic Events [EXCITE] trial).
2008 Nov 1

Sample Use Guides

After elective intracoronary stent deployment, patients were randomized to receive placebo (250 mg ticlopidine P.O. BID) or xemilofiban in doses of 5, 10, 15, or 20 mg P.O. BID.
Route of Administration: Oral
Name Type Language
XEMILOFIBAN
INN   MI   WHO-DD  
INN  
Official Name English
SC54684
Code English
XEMILOFIBAN [MI]
Common Name English
xemilofiban [INN]
Common Name English
SC-54684
Code English
Xemilofiban [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C101256
Created by admin on Fri Dec 15 16:44:51 GMT 2023 , Edited by admin on Fri Dec 15 16:44:51 GMT 2023
Code System Code Type Description
CAS
149820-74-6
Created by admin on Fri Dec 15 16:44:51 GMT 2023 , Edited by admin on Fri Dec 15 16:44:51 GMT 2023
PRIMARY
ChEMBL
CHEMBL76098
Created by admin on Fri Dec 15 16:44:51 GMT 2023 , Edited by admin on Fri Dec 15 16:44:51 GMT 2023
PRIMARY
EVMPD
SUB00099MIG
Created by admin on Fri Dec 15 16:44:51 GMT 2023 , Edited by admin on Fri Dec 15 16:44:51 GMT 2023
PRIMARY
SMS_ID
100000079332
Created by admin on Fri Dec 15 16:44:51 GMT 2023 , Edited by admin on Fri Dec 15 16:44:51 GMT 2023
PRIMARY
MESH
C091295
Created by admin on Fri Dec 15 16:44:51 GMT 2023 , Edited by admin on Fri Dec 15 16:44:51 GMT 2023
PRIMARY
INN
7432
Created by admin on Fri Dec 15 16:44:51 GMT 2023 , Edited by admin on Fri Dec 15 16:44:51 GMT 2023
PRIMARY
NCI_THESAURUS
C152930
Created by admin on Fri Dec 15 16:44:51 GMT 2023 , Edited by admin on Fri Dec 15 16:44:51 GMT 2023
PRIMARY
FDA UNII
P614JI3IYK
Created by admin on Fri Dec 15 16:44:51 GMT 2023 , Edited by admin on Fri Dec 15 16:44:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID60164410
Created by admin on Fri Dec 15 16:44:51 GMT 2023 , Edited by admin on Fri Dec 15 16:44:51 GMT 2023
PRIMARY
PUBCHEM
60957
Created by admin on Fri Dec 15 16:44:51 GMT 2023 , Edited by admin on Fri Dec 15 16:44:51 GMT 2023
PRIMARY
MERCK INDEX
m11539
Created by admin on Fri Dec 15 16:44:51 GMT 2023 , Edited by admin on Fri Dec 15 16:44:51 GMT 2023
PRIMARY Merck Index