Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C14H17N3O4.ClH.H2O |
| Molecular Weight | 345.779 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.Cl.NCC(=O)N1C[C@@H](C[C@H]1C(O)=O)NC(=O)C2=CC=CC=C2
InChI
InChIKey=AMUAXJVNXHQNBH-OXPNAJOUSA-N
InChI=1S/C14H17N3O4.ClH.H2O/c15-7-12(18)17-8-10(6-11(17)14(20)21)16-13(19)9-4-2-1-3-5-9;;/h1-5,10-11H,6-8,15H2,(H,16,19)(H,20,21);1H;1H2/t10-,11+;;/m1../s1
| 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 | C14H17N3O4 |
| Molecular Weight | 291.3025 |
| 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 |
Danegaptide (GAP-134) is a small dipeptide gap junction modifier, developed by Wyeth and Zealand Pharma. Danegaptide works by re-establishing of gap junction intercellular communications in adjacent cardiomyocytes, thus reversing cardiac conduction slowing and electrical heterogeneity thought to be responsible for arrhythmias. In a canine model of acute sterile pericarditis, Danegaptide significantly reduced AF duration and overall AF burden. Danegaptide was investigated in phase 2 clinical trial in patients with ST-segment elevation myocardial infarction (STEMI). It was found that administrations danegaptide to patients with STEMI did not improve myocardial salvage, and development of the drug was discontinued.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| GAP-134 ([2S,4R]-1-[2-aminoacetyl]4-benzamidopyrrolidine-2-carboxylic acid) prevents spontaneous ventricular arrhythmias and reduces infarct size during myocardial ischemia/reperfusion injury in open-chest dogs. | 2009-09 |
|
| Discovery of (2S,4R)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic acid hydrochloride (GAP-134)13, an orally active small molecule gap-junction modifier for the treatment of atrial fibrillation. | 2009-02-26 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 19:53:05 GMT 2025
by
admin
on
Wed Apr 02 19:53:05 GMT 2025
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| Record UNII |
9BK82WY2LV
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| Record Status |
Validated (UNII)
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| Record Version |
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9BK82WY2LV
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1035596-39-4
Created by
admin on Wed Apr 02 19:53:05 GMT 2025 , Edited by admin on Wed Apr 02 19:53:05 GMT 2025
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