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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H22N4O4.ClH
Molecular Weight 394.853
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of XEMILOFIBAN HYDROCHLORIDE

SMILES

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

InChI

InChIKey=JTZJXWLQRZUDFJ-BTQNPOSSSA-N
InChI=1S/C18H22N4O4.ClH/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);1H/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
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).
2008-11-01
Xemilofiban: SC 54684A, xemlofiban.
2003
Acute thrombocytopenia in patients treated with the oral glycoprotein IIb/IIIa inhibitors xemilofiban and orbofiban: evidence for an immune etiology.
2002-12

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
SC-54684A
Preferred Name English
XEMILOFIBAN HYDROCHLORIDE
MART.   MI   USAN  
USAN  
Official Name English
XEMILOFIBAN HYDROCHLORIDE [USAN]
Common Name English
XEMILOFIBAN HCL
Common Name English
XEMILOFIBAN HYDROCHLORIDE [MI]
Common Name English
4-PENTYNOIC ACID, 3-((4-((4-(AMINOIMINOMETHYL)PHENYL)AMINO)-1,4-DIOXOBUTYL)AMINO)-, ETHYL ESTER, MONOHYDROCHLORIDE, (S)-
Common Name English
XEMILOFIBAN HYDROCHLORIDE [MART.]
Common Name English
ETHYL (3S)-3-(3-((P-AMIDINOPHENYL)CARBAMOYL)PROPIONAMIDO)-4-PENTYNOATE, MONOHYDROCHLORIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1327
Created by admin on Mon Mar 31 18:14:26 GMT 2025 , Edited by admin on Mon Mar 31 18:14:26 GMT 2025
Code System Code Type Description
CAS
156586-91-3
Created by admin on Mon Mar 31 18:14:26 GMT 2025 , Edited by admin on Mon Mar 31 18:14:26 GMT 2025
PRIMARY
MERCK INDEX
m11539
Created by admin on Mon Mar 31 18:14:26 GMT 2025 , Edited by admin on Mon Mar 31 18:14:26 GMT 2025
PRIMARY Merck Index
SMS_ID
300000055448
Created by admin on Mon Mar 31 18:14:26 GMT 2025 , Edited by admin on Mon Mar 31 18:14:26 GMT 2025
PRIMARY
NCI_THESAURUS
C63768
Created by admin on Mon Mar 31 18:14:26 GMT 2025 , Edited by admin on Mon Mar 31 18:14:26 GMT 2025
PRIMARY
USAN
GG-85
Created by admin on Mon Mar 31 18:14:26 GMT 2025 , Edited by admin on Mon Mar 31 18:14:26 GMT 2025
PRIMARY
EPA CompTox
DTXSID10166101
Created by admin on Mon Mar 31 18:14:26 GMT 2025 , Edited by admin on Mon Mar 31 18:14:26 GMT 2025
PRIMARY
PUBCHEM
3033830
Created by admin on Mon Mar 31 18:14:26 GMT 2025 , Edited by admin on Mon Mar 31 18:14:26 GMT 2025
PRIMARY
ChEMBL
CHEMBL76098
Created by admin on Mon Mar 31 18:14:26 GMT 2025 , Edited by admin on Mon Mar 31 18:14:26 GMT 2025
PRIMARY
FDA UNII
HIU55WBI80
Created by admin on Mon Mar 31 18:14:26 GMT 2025 , Edited by admin on Mon Mar 31 18:14:26 GMT 2025
PRIMARY