ZP 1609 - CAS 943134-39-2
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
ZP 1609
Catalog Number:
943134-39-2
Synonyms:
GAP-134;(2S,4R)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic acid;Danegaptide;GAP 134; ZP-1609
CAS Number:
943134-39-2
Description:
ZP 1609, a small modified dipeptide, has been identified as a potent and selective second generation gap junction modifier with oral bioavailability. It is a pharmalogical agent with a favorable clinical safety profile and potential antiarrhythmic efficacy, which is confirmed in phase I clinical trials. It is used for the treatment of atrial fibrillation. It improves conduction and reduces atrial fibrillation or flutter in the canine sterile pericarditis model. It prevents spontaneous ventricular arrhythmias and reduces infarct size during myocardial ischemia/reperfusion injury in open-chest dogs. It showed consistent efficacy on measures of conduction and AF/AFL inducibility in the canine sterile pericarditis model. It was developed by Zealand Pharma and was termination in Clinical phase II.
Molecular Weight:
291.30
Molecular Formula:
C14H17N3O4
Quantity:
Milligrams-Grams
Quality Standard:
In-house standard
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
C1C(CN(C1C(=O)O)C(=O)CN)NC(=O)C2=CC=CC=C2
InChI:
InChI=1S/C14H17N3O4/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)/t10-,11+/m1/s1
InChIKey:
BIZKIHUJGMSVFD-MNOVXSKESA-N
Targets:
Gap Junction Protein
Current Developer:
ZP 1609 was developed by Zealand Pharma and was termination in Clinical phase II.
Chemical Structure
CAS 943134-39-2 ZP 1609

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Reference Reading


1.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.
Butera JA1, Larsen BD, Hennan JK, Kerns E, Di L, Alimardanov A, Swillo RE, Morgan GA, Liu K, Wang Q, Rossman EI, Unwalla R, McDonald L, Huselton C, Petersen JS. J Med Chem. 2009 Feb 26;52(4):908-11. doi: 10.1021/jm801558d.
Rotigaptide (3) is an antiarrhythmic peptide that improves cardiac conduction by modifying gap-junction communication. Small molecule gap-junction modifiers with improved physical properties were identified from a Zealand Pharma peptide library using pharmaceutical profiling, established SAR around 3, and a putative pharmacophore model for rotigaptide. Activity of the compounds was confirmed in a mouse cardiac conduction block model of arrhythmia. Dipeptide 9f (GAP-134) was identified as a potent, orally active gap-junction modifier for clinical development.
2.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.
Hennan JK1, Swillo RE, Morgan GA, Rossman EI, Kantrowitz J, Butera J, Petersen JS, Gardell SJ, Vlasuk GP. J Cardiovasc Pharmacol Ther. 2009 Sep;14(3):207-14. doi: 10.1177/1074248409340779.
The antiarrhythmic dipeptide, GAP-134, ([2S,4R]-1[2-aminoacetyl]-4-benzamido-pyrrolidine-2-carboxylic acid) was evaluated in canine ischemia/reperfusion model. In dogs subjected to 60-minute ischemia and 4-hour reperfusion, GAP-134 was administered 10 minutes before reperfusion as a bolus + intravenous (IV) infusion. The doses administered were 0.25 microg/kg bolus + 0.19 microg/kg per hour infusion; 2.5 microg/kg + 1.9 microg/kg per hour; 25 mg/kg + 19 mg/kg per hour; 75 mg/kg + 57 mg/kg per hour. Ventricular ectopy was quantified during reperfusion, including premature ventricular contractions (PVC) and ventricular tachycardia (VT). Total incidence of VT was reduced significantly with the 2 highest doses of GAP-134 (1.7 + 0.8; 2.2 + 1.4 events; P < .05) compared to controls (23.0 + 6.1). Total PVCs were reduced significantly from 11.1 + 1.6% in control animals to 2.0% + 0.7% and 1.8% + 0.8% after the 2 highest doses of GAP-134. Infarct size, expressed as percentage of left ventricle, was reduced significantly from 19.