Danegaptide

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 319822

CAS#: 943134-39-2 (free base)

Description: Danegaptide, also known as GAP-134 and ZP1609, is an orally active small molecule gap-junction modifier for the treatment of atrial fibrillation. Danegaptide mproves conduction and reduces atrial fibrillation/flutter in the canine sterile pericarditis model. Danegaptide prevents spontaneous ventricular arrhythmias and reduces infarct size during myocardial ischemia/reperfusion injury in open-chest dogs.


Chemical Structure

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Danegaptide
CAS# 943134-39-2 (free base)

Theoretical Analysis

MedKoo Cat#: 319822
Name: Danegaptide
CAS#: 943134-39-2 (free base)
Chemical Formula: C14H17N3O4
Exact Mass: 291.1219
Molecular Weight: 291.307
Elemental Analysis: C, 57.72; H, 5.88; N, 14.42; O, 21.97

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Related CAS #: 943134-39-2 (free base)   943133-81-1 (HCl)    

Synonym: GAP-134; GAP 134; GAP134; ZP1609; ZP-1609; ZP 1609; Danegaptide

IUPAC/Chemical Name: (2S,4R)-4-benzamido-1-glycylpyrrolidine-2-carboxylic acid

InChi Key: BIZKIHUJGMSVFD-MNOVXSKESA-N

InChi Code: 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

SMILES Code: O=C(O)[C@H]1N(C(CN)=O)C[C@H](NC(C2=CC=CC=C2)=O)C1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 291.307 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Michela P, Velia V, Aldo P, Ada P. Role of connexin 43 in cardiovascular diseases. Eur J Pharmacol. 2015 Dec 5;768:71-6. doi: 10.1016/j.ejphar.2015.10.030. Epub 2015 Oct 20. Review. PubMed PMID: 26499977.

2: De Vuyst E, Boengler K, Antoons G, Sipido KR, Schulz R, Leybaert L. Pharmacological modulation of connexin-formed channels in cardiac pathophysiology. Br J Pharmacol. 2011 Jun;163(3):469-83. doi: 10.1111/j.1476-5381.2011.01244.x. Review. PubMed PMID: 21265827; PubMed Central PMCID: PMC3101610.

3: Dhein S, Hagen A, Jozwiak J, Dietze A, Garbade J, Barten M, Kostelka M, Mohr FW. Improving cardiac gap junction communication as a new antiarrhythmic mechanism: the action of antiarrhythmic peptides. Naunyn Schmiedebergs Arch Pharmacol. 2010 Mar;381(3):221-34. doi: 10.1007/s00210-009-0473-1. Epub 2009 Nov 27. Review. PubMed PMID: 19943035.

4: Laurent G, Leong-Poi H, Mangat I, Moe GW, Hu X, So PP, Tarulli E, Ramadeen A, Rossman EI, Hennan JK, Dorian P. Effects of chronic gap junction conduction-enhancing antiarrhythmic peptide GAP-134 administration on experimental atrial fibrillation in dogs. Circ Arrhythm Electrophysiol. 2009 Apr;2(2):171-8. doi: 10.1161/CIRCEP.108.790212. Epub 2009 Feb 13. PubMed PMID: 19808462.

5: Hennan JK, Swillo RE, Morgan GA, Rossman EI, Kantrowitz J, Butera J, Petersen JS, Gardell SJ, Vlasuk GP. 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. J Cardiovasc Pharmacol Ther. 2009 Sep;14(3):207-14. doi: 10.1177/1074248409340779. PubMed PMID: 19721133.

6: Piatnitski Chekler EL, Butera JA, Di L, Swillo RE, Morgan GA, Rossman EI, Huselton C, Larsen BD, Hennan JK. Discovery of a class of potent gap-junction modifiers as novel antiarrhythmic agents. Bioorg Med Chem Lett. 2009 Aug 15;19(16):4551-4. doi: 10.1016/j.bmcl.2009.07.014. Epub 2009 Jul 9. PubMed PMID: 19616941.

7: Rossman EI, Liu K, Morgan GA, Swillo RE, Krueger JA, Gardell SJ, Butera J, Gruver M, Kantrowitz J, Feldman HS, Petersen JS, Haugan K, Hennan JK. The gap junction modifier, GAP-134 [(2S,4R)-1-(2-aminoacetyl)-4-benzamido-pyrrolidine-2-carboxylic acid], improves conduction and reduces atrial fibrillation/flutter in the canine sterile pericarditis model. J Pharmacol Exp Ther. 2009 Jun;329(3):1127-33. doi: 10.1124/jpet.108.150102. Epub 2009 Feb 27. PubMed PMID: 19252062.

8: Butera JA, 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. 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. J Med Chem. 2009 Feb 26;52(4):908-11. doi: 10.1021/jm801558d. PubMed PMID: 19175320.