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MedKoo Cat#: 530206 | Name: Rotigaptide

Description:

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

Rotigaptide, also known as GAP-486; ZP-123, is a gap junction modulator potentially for the treatment of ventricular tachycardia and atrial.

Chemical Structure

Rotigaptide
Rotigaptide
CAS#355151-12-1

Theoretical Analysis

MedKoo Cat#: 530206

Name: Rotigaptide

CAS#: 355151-12-1

Chemical Formula: C28H39N7O9

Exact Mass: 617.2809

Molecular Weight: 617.66

Elemental Analysis: C, 54.45; H, 6.36; N, 15.87; O, 23.31

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
GAP-486; ZP-123; GAP486; ZP123; GAP 486; ZP 123; Rotigaptide.
IUPAC/Chemical Name
Glycinamide, N-acetyl-D-tyrosyl-D-prolyl-(4S)-4-hydroxy-D-prolylglycyl-D-alanyl-
InChi Key
GFJRASPBQLDRRY-TWTQBQJDSA-N
InChi Code
InChI=1S/C28H39N7O9/c1-15(25(41)30-12-23(29)39)32-24(40)13-31-26(42)22-11-19(38)14-35(22)28(44)21-4-3-9-34(21)27(43)20(33-16(2)36)10-17-5-7-18(37)8-6-17/h5-8,15,19-22,37-38H,3-4,9-14H2,1-2H3,(H2,29,39)(H,30,41)(H,31,42)(H,32,40)(H,33,36)/t15-,19+,20-,21-,22-/m1/s1
SMILES Code
O=C(N)CNC([C@@H](C)NC(CNC([C@@H]1N(C([C@@H]2N(C([C@@H](CC3=CC=C(O)C=C3)NC(C)=O)=O)CCC2)=O)C[C@@H](O)C1)=O)=O)=O
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
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 617.66 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
1: Ng FS, Kalindjian JM, Cooper SA, Chowdhury RA, Patel PM, Dupont E, Lyon AR, Peters NS. Enhancement of Gap Junction Function During Acute Myocardial Infarction Modifies Healing and Reduces Late Ventricular Arrhythmia Susceptibility. JACC Clin Electrophysiol. 2016 Oct;2(5):574-582. PubMed PMID: 27807593; PubMed Central PMCID: PMC5076465. 2: Pedersen CM, Venkatasubramanian S, Vase H, Hyldebrandt JA, Contractor H, Schmidt MR, Bøtker HE, Cruden NL, Newby DE, Kharbanda RK, Lang NN. Rotigaptide protects the myocardium and arterial vasculature from ischaemia reperfusion injury. Br J Clin Pharmacol. 2016 Jun;81(6):1037-45. doi: 10.1111/bcp.12882. PubMed PMID: 26750458. 3: Su GY, Wang J, Xu ZX, Qiao XJ, Zhong JQ, Zhang Y. [Corrigendum] Effects of rotigaptide (ZP123) on connexin43 remodeling in canine ventricular fibrillation. Mol Med Rep. 2015 Dec;12(6):8327. doi: 10.3892/mmr.2015.4472. PubMed PMID: 26499056; PubMed Central PMCID: PMC4758342. 4: Su GY, Wang J, Xu ZX, Qiao XJ, Zhong JQ, Zhang Y. Effects of rotigaptide (ZP123) on connexin43 remodeling in canine ventricular fibrillation. Mol Med Rep. 2015 Oct;12(4):5746-52. doi: 10.3892/mmr.2015.4193. Erratum in: Mol Med Rep. 2015 Dec;12(6):8327. PubMed PMID: 26252617; PubMed Central PMCID: PMC4581824. 5: Hsieh YC, Lin JC, Hung CY, Li CH, Lin SF, Yeh HI, Huang JL, Lo CP, Haugan K, Larsen BD, Wu TJ. Gap junction modifier rotigaptide decreases the susceptibility to ventricular arrhythmia by enhancing conduction velocity and suppressing discordant alternans during therapeutic hypothermia in isolated rabbit hearts. Heart Rhythm. 2016 Jan;13(1):251-61. doi: 10.1016/j.hrthm.2015.07.023. PubMed PMID: 26188250. 6: Ueda N, Yamamoto M, Honjo H, Kodama I, Kamiya K. The role of gap junctions in stretch-induced atrial fibrillation. Cardiovasc Res. 2014 Nov 1;104(2):364-70. doi: 10.1093/cvr/cvu202. PubMed PMID: 25183791; PubMed Central PMCID: PMC4217686. 7: Gao L, Cheng C, Sparatore A, Zhang H, Wang C. Hydrogen sulfide inhibits human platelet aggregation in vitro in part by interfering gap junction channels: effects of ACS14, a hydrogen sulfide-releasing aspirin. Heart Lung Circ. 2015 Jan;24(1):77-85. doi: 10.1016/j.hlc.2014.05.019. PubMed PMID: 25047282. 8: Liu Y, Li H, Xia W, Yu S, Huang C, Huang H. Electrophysiological effect of rotigaptide in rabbits with heart failure. Arch Med Sci. 2014 May 12;10(2):374-80. doi: 10.5114/aoms.2012.31385. PubMed PMID: 24904675; PubMed Central PMCID: PMC4042033. 9: Tsang H, Leiper J, Hou Lao K, Dowsett L, Delahaye MW, Barnes G, Wharton J, Howard L, Iannone L, Lang NN, Wilkins MR, Wojciak-Stothard B. Role of asymmetric methylarginine and connexin 43 in the regulation of pulmonary endothelial function. Pulm Circ. 2013 Sep;3(3):675-91. doi: 10.1086/674440. PubMed PMID: 24618552; PubMed Central PMCID: PMC4070793. 10: Skyschally A, Walter B, Schultz Hansen R, Heusch G. The antiarrhythmic dipeptide ZP1609 (danegaptide) when given at reperfusion reduces myocardial infarct size in pigs. Naunyn Schmiedebergs Arch Pharmacol. 2013 May;386(5):383-91. doi: 10.1007/s00210-013-0840-9. PubMed PMID: 23397587. 11: Yi SL, Zhong JQ, Zhang J, Su GY, Li JS, Liu HZ, Zhang Y. ZP123 reduces energy required for defibrillation by preventing connexin43 remodeling during prolonged ventricular fibrillation in swine. Tex Heart Inst J. 2012;39(6):784-91. PubMed PMID: 23304014; PubMed Central PMCID: PMC3528250. 12: Takemoto Y, Takanari H, Honjo H, Ueda N, Harada M, Kato S, Yamazaki M, Sakuma I, Opthof T, Kodama I, Kamiya K. Inhibition of intercellular coupling stabilizes spiral-wave reentry, whereas enhancement of the coupling destabilizes the reentry in favor of early termination. Am J Physiol Heart Circ Physiol. 2012 Sep 1;303(5):H578-86. doi: 10.1152/ajpheart.00355.2012. PubMed PMID: 22707561. 13: Li JS, Zhong JQ, Zeng QX, Liu HZ, Su GY, Zhang Y. Effect of ZP123, a gap junction modifier, on prolonged ventricular fibrillation in swine. Cardiology. 2011;118(3):147-52. doi: 10.1159/000328016. PubMed PMID: 21606647. 14: Macia E, Dolmatova E, Cabo C, Sosinsky AZ, Dun W, Coromilas J, Ciaccio EJ, Boyden PA, Wit AL, Duffy HS. Characterization of gap junction remodeling in epicardial border zone of healing canine infarcts and electrophysiological effects of partial reversal by rotigaptide. Circ Arrhythm Electrophysiol. 2011 Jun;4(3):344-51. doi: 10.1161/CIRCEP.110.959312. PubMed PMID: 21493965; PubMed Central PMCID: PMC3116056. 15: Liu HZ, Zhong JQ, Li JS, Su GY, Wang J, Zhang Y. [Changes in myocardial connexin 43 during ventricular fibrillation]. Zhongguo Wei Zhong Bing Ji Jiu Yi Xue. 2010 Oct;22(10):595-8. Chinese. PubMed PMID: 20977841. 16: Myles RC, Bernus O, Burton FL, Cobbe SM, Smith GL. Effect of activation sequence on transmural patterns of repolarization and action potential duration in rabbit ventricular myocardium. Am J Physiol Heart Circ Physiol. 2010 Dec;299(6):H1812-22. doi: 10.1152/ajpheart.00518.2010. PubMed PMID: 20889843; PubMed Central PMCID: PMC3006295. 17: Gramley F, Himmrich E, Mollnau H, Theis C, Hammwohner M, Goette A. Recent advances in the pharmacological treatment of cardiac arrythmias. Drugs Today (Barc). 2009 Nov;45(11):807-24. doi: 10.13581/dot.2009.45.11.1412574. Review. Erratum in: Drugs Today (Barc). 2010 Jan;46(1):69. PubMed PMID: 20126673. 18: 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. Review. PubMed PMID: 19943035. 19: Singh B. Atrial fibrillation: from ion channels to bedside treatment options. J Electrocardiol. 2009 Nov-Dec;42(6):660-70. doi: 10.1016/j.jelectrocard.2009.04.002. Review. PubMed PMID: 19520377. 20: 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. PubMed PMID: 19252062.

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