SIBRAFIBAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H28N4O6
Molecular Weight	420.4595
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)COC1CCN(CC1)C(=O)[C@H](C)NC(=O)C2=CC=C(C=C2)C(\N)=N\O

InChI

InChIKey=WBNUCLPUOSXSNJ-ZDUSSCGKSA-N

InChI=1S/C20H28N4O6/c1-3-29-17(25)12-30-16-8-10-24(11-9-16)20(27)13(2)22-19(26)15-6-4-14(5-7-15)18(21)23-28/h4-7,13,16,28H,3,8-12H2,1-2H3,(H2,21,23)(H,22,26)/t13-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10188763 | https://www.ncbi.nlm.nih.gov/pubmed/16155849 | https://adisinsight.springer.com/drugs/800006751 | https://www.ncbi.nlm.nih.gov/pubmed/9733353

Sibrafiban (G-7453) is the orally administered, nonpeptide, double-prodrug of Ro 44-3888 which is a selective glycoprotein IIb/IIIa receptor antagonist. Sibrafiban is a double prodrug that undergoes bioconversion to the inactive prodrug Ro 48-3656 and to the active IIb/IIIa antagonist, Ro 44-3888, after oral administration. Sibrafiban was undergoing clinical trials for secondary prevention of cardiac events in patients stabilised after acute coronary syndromes. Sibrafiban has been shown to have comparable efficacy to aspirin in preventing recurrent ischemic events in patients suffering from acute coronary syndromes. Sibrafiban was under development by Genentech and Hoffmann-La Roche, and in phase III trials as an antithrombotic. The development of sibrafiban was discontinued in 1999 following unfavorable Phase III efficacy data.

Originator

Approval Year

PubMed

Title	Date	PubMed
Sibrafiban.	1999 Feb	10188763

Sample Use Guides

In Vivo Use Guide

Patients who had stabilised after an acute coronary syndrome event were randomly assigned aspirin (80 mg orally twice daily) or low-dose or high-dose sibrafiban. Sibrafiban doses (3.0 mg, 4.5 mg, or 6.0 mg) were based on a model accounting for weight and serum creatinine and designed to achieve at least 25% steady-state inhibition of platelet aggregation (low dose) or at least 50% inhibition (high dose). The primary endpoint was the composite of death, non-fatal infarction or reinfarction, or severe recurrent ischaemia at 90 days.

Route of Administration: Oral

In Vitro Use Guide

Sibrafiban inhibited shear-induced platelet activation and adhesion with IC50 value of 43 nM.

Name

Type

Language

SIBRAFIBAN

Official Name

English

ACETIC ACID, ((1-(2-((4-((HYDROXYAMINO)IMINOMETHYL)BENZOYL)AMINO)-1-OXOPROPYL)-4-PIPERIDINYL)OXY)-, ETHYL ESTER, (S)-

Common Name

English

ETHYL (Z)-((1-(N-((P-HYDROXYAMIDINO)BENZOYL)-L-ALANYL)-4-PIPERIDYL)OXY)ACETATE

Common Name

English

RO-48-3657/001

Code

English

RO 48-3657/001

Code

English

ACETIC ACID, ((1-(2-((4-(AMINO(HYDROXYIMINO)METHYL)BENZOYLAMINO)-1-OXOPROPYL)-4-PIPERIDINYL)OXY)-, ETHYL ESTER, (S-(Z))-

Common Name

English

SIBRAFIBAN [MART.]

Common Name

English

Sibrafiban [WHO-DD]

Common Name

English

RO-48-3657

Code

English

SIBRAFIBAN [USAN]

Common Name

English

RO-483657001

Code

English

ACETIC ACID, ((1-((2S)-2-((4-((HYDROXYAMINO)IMINOMETHYL)BENZOYL)AMINO)-1-OXOPROPYL)-4-PIPERIDINYL)OXY)-, ETHYL ESTER

Common Name

English

sibrafiban [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1327