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

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

Molecular Formula	C24H28N4O6
Molecular Weight	468.5023
Charge	0
Count

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

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 2778		1.4 nM [IC50]

PubMed

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

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:03:53 GMT 2023` Edited by `admin` on `Fri Dec 15 16:03:53 GMT 2023`
Record UNII	3UZ1CTQ989
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LAMIFIBAN HYDROCHLORIDE

Official 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

RO 44-9883/023

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C1327