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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H18N4O4
Molecular Weight 330.3385
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of XEMILOFIBAN ACID

SMILES

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

InChI

InChIKey=OUZLOTRPGMFLPN-LLVKDONJSA-N
InChI=1S/C16H18N4O4/c1-2-11(9-15(23)24)19-13(21)7-8-14(22)20-12-5-3-10(4-6-12)16(17)18/h1,3-6,11H,7-9H2,(H3,17,18)(H,19,21)(H,20,22)(H,23,24)/t11-/m1/s1

HIDE SMILES / InChI

Molecular Formula C16H18N4O4
Molecular Weight 330.3385
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Xemilofiban: SC 54684A, xemlofiban.
2003
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:35:54 GMT 2023
Edited
by admin
on Sat Dec 16 08:35:54 GMT 2023
Record UNII
TN585Y92BI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
XEMILOFIBAN ACID
MI  
Common Name English
4-PENTYNOIC ACID, 3-((4-((4-(AMINOIMINOMETHYL)PHENYL)AMINO)-1,4-DIOXOBUTYL)AMINO)-, (3S)-
Systematic Name English
SC54701
Code English
XEMILOFIBAN ACID [MI]
Common Name English
SC-54701
Code English
Code System Code Type Description
PUBCHEM
9862322
Created by admin on Sat Dec 16 08:35:54 GMT 2023 , Edited by admin on Sat Dec 16 08:35:54 GMT 2023
PRIMARY
FDA UNII
TN585Y92BI
Created by admin on Sat Dec 16 08:35:54 GMT 2023 , Edited by admin on Sat Dec 16 08:35:54 GMT 2023
PRIMARY
MERCK INDEX
m11539
Created by admin on Sat Dec 16 08:35:54 GMT 2023 , Edited by admin on Sat Dec 16 08:35:54 GMT 2023
PRIMARY Merck Index
CAS
149193-61-3
Created by admin on Sat Dec 16 08:35:54 GMT 2023 , Edited by admin on Sat Dec 16 08:35:54 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY