ELAROFIBAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H32N4O4.H2O
Molecular Weight	434.5292
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.OC(=O)C[C@H](NC(=O)[C@@H]1CCCN(C1)C(=O)CCC2CCNCC2)C3=CN=CC=C3

InChI

InChIKey=VHTVZWUXMIOMAD-VOMIJIAVSA-N

InChI=1S/C22H32N4O4.H2O/c27-20(6-5-16-7-10-23-11-8-16)26-12-2-4-18(15-26)22(30)25-19(13-21(28)29)17-3-1-9-24-14-17;/h1,3,9,14,16,18-19,23H,2,4-8,10-13,15H2,(H,25,30)(H,28,29);1H2/t18-,19+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C22H32N4O4
Molecular Weight	416.5139
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	H2O
Molecular Weight	18.0153
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/11672755
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/17115723 | http://adisinsight.springer.com/drugs/800010575

Elarofiban is a novel nonpeptide glycoprotein IIb/IIIa (GPIIb/IIIa) antagonist. It inhibits thrombin-induced platelet aggregation in human gel-filtered platelets and platelet aggregation in human platelet-rich plasma (PRP) in response to collagen, arachidonic acid, ADP, and SFLLRN-NH(2). Elarofiban had adequate oral pharmacokinetics in dogs and excellent oral pharmacodynamics. Elarofiban has been in phase II clinical trials for the treatment of myocardial infarction and thrombosis. However, this research has been discontinued.

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/28302764 \| https://www.ncbi.nlm.nih.gov/pubmed/11672755	Antagonist 2778		19.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Thrombosis 22 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11672755 https://www.ncbi.nlm.nih.gov/pubmed/10602710	Primary		Phase II 1132	Unknown Approved Use Unknown
Myocardial infarction 121 Sources: http://en.pharmacodia.com/web/drug/1_5802.html	Primary		Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
Compound Cloud	216230
Compound Cloud	216231
MuseChem	I006595	https://www.musechem.com/product/I006595.html
eMolecules	107053048	https://orderbb.emolecules.com/search/#?query=107053048
eMolecules	76746817	https://orderbb.emolecules.com/search/#?query=76746817

PubMed

Title	Date	PubMed
Potent, orally active GPIIb/IIIa antagonists containing a nipecotic acid subunit. Structure-activity studies leading to the discovery of RWJ-53308.	1999 Dec 16	10602710
Optimizing Caco-2 cell monolayers to increase throughput in drug intestinal absorption analysis.	2001 Jul-Aug	12164260
Antiplatelet and antithrombotic activity of RWJ-53308, a novel orally active glycoprotein IIb/IIIa antagonist.	2001 Oct 15	11672755
1,2,4-triazolo[3,4-a]pyridine as a novel, constrained template for fibrinogen receptor (GPIIb/IIIa) antagonists.	2001 Oct 8	11551763
(18)F-GP1, a Novel PET Tracer Designed for High-Sensitivity, Low-Background Detection of Thrombi.	2017 Jul	28302764

Patents

Sample Use Guides

In Vivo Use Guide

Oral: 3 mg/kg Intravenous: 0.03 mg/kg

Route of Administration: Other

In Vitro Use Guide

Elarofiban inhibited platelet aggregation in human platelet-rich plasma in response to multiple agonists (collagen, ADP, TRAP-6, arachidonic acid; IC50 = 60-160 nM).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:30:26 UTC 2023` Edited by `admin` on `Fri Dec 15 16:30:26 UTC 2023`
Record UNII	6Y891C0JEV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ELAROFIBAN

Official Name

English

3-PYRIDINEPROPANOIC ACID, .BETA.-(((1-(1-OXO-3-(4-PIPERIDINYL)PROPYL)-3-PIPERIDINYL)CARBONYL)AMINO)-, (S-(R*,S*))-, MONOHYDRATE

Common Name

English

RWJ-53308

Code

English

(S)-β-[(R)-1-[3-(4-Piperidyl)propionyl]nipecotamido]-3-pyridinepropionic acid, monohydrate

Common Name

English

ELAROFIBAN [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29750