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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H32N4O4
Molecular Weight 416.5147
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ELAROFIBAN ANHYDROUS

SMILES

c1cc(cnc1)[C@]([H])(CC(=O)O)N=C([C@]2([H])CCCN(C2)C(=O)CCC3CCNCC3)O

InChI

InChIKey=ABNXKGFLZFSILK-MOPGFXCFSA-N
InChI=1S/C22H32N4O4/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)/t18-,19+/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H32N4O4
Molecular Weight 416.5147
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Curator's Comment:: the subsidiary of Johnson & Johnson

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
19.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

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

Sample Use Guides

Oral: 3 mg/kg Intravenous: 0.03 mg/kg
Route of Administration: Other
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 Sat Jun 26 16:39:47 UTC 2021
Edited
by admin
on Sat Jun 26 16:39:47 UTC 2021
Record UNII
T9YH5NSL8U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ELAROFIBAN ANHYDROUS
Common Name English
ELAROFIBAN [INN]
Common Name English
(S)-.BETA.-((R)-1-(3-(4-PIPERIDYL)PROPIONYL)NIPECOTAMIDO)-3-PYRIDINEPROPIONIC ACID
Systematic Name English
3-PYRIDINEPROPANOIC ACID, .BETA.-(((1-(1-OXO-3-(4-PIPERIDINYL)PROPYL)-3-PIPERIDINYL)CARBONYL)AMINO)-, (S-(R*,S*))-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29750
Created by admin on Sat Jun 26 16:39:47 UTC 2021 , Edited by admin on Sat Jun 26 16:39:47 UTC 2021
Code System Code Type Description
PUBCHEM
216230
Created by admin on Sat Jun 26 16:39:47 UTC 2021 , Edited by admin on Sat Jun 26 16:39:47 UTC 2021
PRIMARY
NCI_THESAURUS
C80842
Created by admin on Sat Jun 26 16:39:47 UTC 2021 , Edited by admin on Sat Jun 26 16:39:47 UTC 2021
PRIMARY
CAS
198958-88-2
Created by admin on Sat Jun 26 16:39:47 UTC 2021 , Edited by admin on Sat Jun 26 16:39:47 UTC 2021
PRIMARY
FDA UNII
T9YH5NSL8U
Created by admin on Sat Jun 26 16:39:47 UTC 2021 , Edited by admin on Sat Jun 26 16:39:47 UTC 2021
PRIMARY
INN
8001
Created by admin on Sat Jun 26 16:39:47 UTC 2021 , Edited by admin on Sat Jun 26 16:39:47 UTC 2021
PRIMARY
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SALT/SOLVATE -> PARENT
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ACTIVE MOIETY