LAMIFIBAN HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H28N4O6.ClH
Molecular Weight	504.963
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.NC(=N)C1=CC=C(C=C1)C(=O)N[C@@H](CC2=CC=C(O)C=C2)C(=O)N3CCC(CC3)OCC(O)=O

InChI

InChIKey=YUWYXULCUNUQCG-BDQAORGHSA-N

InChI=1S/C24H28N4O6.ClH/c25-22(26)16-3-5-17(6-4-16)23(32)27-20(13-15-1-7-18(29)8-2-15)24(33)28-11-9-19(10-12-28)34-14-21(30)31;/h1-8,19-20,29H,9-14H2,(H3,25,26)(H,27,32)(H,30,31);1H/t20-;/m0./s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/mesh/67084062 | https://www.ncbi.nlm.nih.gov/pubmed/8759635 | https://www.ncbi.nlm.nih.gov/pubmed/11804986

LAMIFIBAN is a potent and selective nonpeptide glycoprotein IIb/IIIa antagonist. It inhibits platelet aggregation and thrombus formation by preventing the binding of fibrinogen to platelets. It was in clinical development as an injectable antithrombotic agent for treating and preventing acute coronary syndromes but showed no significant effects on clinical outcomes.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Integrin alpha-IIb/beta-3 14 Target ID: CHEMBL2093869 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8759635	Antagonist 2849		1.4 nM [IC50]

PubMed

Title	Date	PubMed
Randomized, placebo-controlled trial of titrated intravenous lamifiban for acute coronary syndromes.	2002-01-22	11804986
Lamifiban.	1999-05	10566069
Lamifiban.	1999-02	10188762
Orally active fibrinogen receptor antagonists. 2. Amidoximes as prodrugs of amidines.	1996-08-02	8759635

Patents

Name

Type

Language

LAMIFIBAN HYDROCHLORIDE

Official Name

English

RO 44-9883/023

Preferred Name

English

(S)-((1-(2-((4-(AMINOIMINOMETHYL)BENZOYL)AMINO)-3-(4-HYDROXYPHENYL)-1-OXOPROPYL)-4-PIPERIDINYL)OXY)ACETIC ACID MONOHYDROCHLORIDE

Systematic Name

English

((1-(N-(P-AMIDINOBENZOYL)-L-TYROSYL)-4-PIPERIDYL)OXY)ACETIC ACID MONOHYDROCHLORIDE

Common Name

English

LAMIFIBAN HCL

Common Name

English

LAMIFIBAN HYDROCHLORIDE [USAN]

Common Name

English

RO-44-9883/023

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1327