XEMILOFIBAN HYDROCHLORIDE

Possibly Marketed Outside US

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 Search

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

Molecular Formula	C18H22N4O4
Molecular Weight	358.3917
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14584975 | http://www.virtualdrugdevelopment.com/Xemilofiban1.htm

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

Title	Date	PubMed
Acute thrombocytopenia in patients treated with the oral glycoprotein IIb/IIIa inhibitors xemilofiban and orbofiban: evidence for an immune etiology.	2002 Dec	12529735
Xemilofiban: SC 54684A, xemlofiban.	2003	14584975
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	18940282

Sample Use Guides

In Vivo Use Guide

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 `Fri Dec 15 15:57:17 GMT 2023` Edited by `admin` on `Fri Dec 15 15:57:17 GMT 2023`
Record UNII	HIU55WBI80
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

XEMILOFIBAN HYDROCHLORIDE

Official Name

English

XEMILOFIBAN HYDROCHLORIDE [USAN]

Common Name

English

SC-54684A

Code

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