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Rotigaptide

Rotigaptide

  • CAT Number: I008729
  • CAS Number: 355151-12-1
  • Molecular Formula: C28H39N7O9
  • Molecular Weight: 617.66
  • Purity: ≥95%
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Rotigaptide (CAS 355151-12-1), also known as GAP-486; ZP-123, is a gap junction modulator potentially for the treatment of ventricular tachycardia and atrial.

Catalog Number I008729
CAS Number 355151-12-1
Synonyms

GAP-486; ZP-123; GAP486; ZP123; GAP 486; ZP 123; Rotigaptide.;Glycinamide, N-acetyl-D-tyrosyl-D-prolyl-(4S)-4-hydroxy-D-prolylglycyl-D-alanyl-

Molecular Formula

C28H39N7O9

Purity 95%
Target gap junction modulator
Solubility Soluble in DMSO
Storage 0 - 4 °C for short term, or -20 °C for long term
IUPAC Name (2R,4S)-1-[(2R)-1-[(2R)-2-acetamido-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]-N-[2-[[(2R)-1-[(2-amino-2-oxoethyl)amino]-1-oxopropan-2-yl]amino]-2-oxoethyl]-4-hydroxypyrrolidine-2-carboxamide
InChI 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
InChIKey GFJRASPBQLDRRY-TWTQBQJDSA-N
SMILES CC(C(=O)NCC(=O)N)NC(=O)CNC(=O)C1CC(CN1C(=O)C2CCCN2C(=O)C(CC3=CC=C(C=C3)O)NC(=O)C)O
Reference

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1:Rotigaptide protects the myocardium and arterial vasculature from ischaemia reperfusion injury. Pedersen CM, Venkatasubramanian S, Vase H, Hyldebrandt JA, Contractor H, Schmidt MR, B&oslash;tker HE, Cruden NL, Newby DE, Kharbanda RK, Lang NN.Br J Clin Pharmacol. 2016 Jun;81(6):1037-45. doi: 10.1111/bcp.12882. Epub 2016 Mar 10. PMID: 26750458<br />
2:[Corrigendum] Effects of rotigaptide (ZP123) on connexin43 remodeling in canine ventricular fibrillation. Su GY, Wang J, Xu ZX, Qiao XJ, Zhong JQ, Zhang Y.Mol Med Rep. 2015 Dec;12(6):8327. doi: 10.3892/mmr.2015.4472. Epub 2015 Oct 23. No abstract available. PMID: 26499056 Free PMC Article<br />
3:Effects of rotigaptide (ZP123) on connexin43 remodeling in canine ventricular fibrillation. Su GY, Wang J, Xu ZX, Qiao XJ, Zhong JQ, Zhang Y.Mol Med Rep. 2015 Oct;12(4):5746-52. doi: 10.3892/mmr.2015.4193. Epub 2015 Aug 6. Erratum in: Mol Med Rep. 2015 Dec;12(6):8327. PMID: 26252617 Free PMC Article<br />
4: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. Hsieh YC, Lin JC, Hung CY, Li CH, Lin SF, Yeh HI, Huang JL, Lo CP, Haugan K, Larsen BD, Wu TJ.Heart Rhythm. 2016 Jan;13(1):251-61. doi: 10.1016/j.hrthm.2015.07.023. Epub 2015 Jul 15. PMID: 26188250<br />
5:Electrophysiological effect of rotigaptide in rabbits with heart failure. Liu Y, Li H, Xia W, Yu S, Huang C, Huang H.Arch Med Sci. 2014 May 12;10(2):374-80. doi: 10.5114/aoms.2012.31385. Epub 2012 Oct 30. PMID: 24904675 Free PMC Article<br />
6:Characterization of gap junction remodeling in epicardial border zone of healing canine infarcts and electrophysiological effects of partial reversal by rotigaptide. Macia E, Dolmatova E, Cabo C, Sosinsky AZ, Dun W, Coromilas J, Ciaccio EJ, Boyden PA, Wit AL, Duffy HS.Circ Arrhythm Electrophysiol. 2011 Jun;4(3):344-51. doi: 10.1161/CIRCEP.110.959312. Epub 2011 Apr 14. PMID: 21493965 Free PMC Article<br />
7:The vascular effects of rotigaptide in vivo in man. Lang NN, Myles RC, Burton FL, Hall DP, Chin YZ, Boon NA, Newby DE.Biochem Pharmacol. 2008 Nov 15;76(10):1194-200. doi: 10.1016/j.bcp.2008.08.022. Epub 2008 Aug 27. PMID: 18789901<br />
8:Enhancement of ventricular gap-junction coupling by rotigaptide. Lin X, Zemlin C, Hennan JK, Petersen JS, Veenstra RD.Cardiovasc Res. 2008 Aug 1;79(3):416-26. doi: 10.1093/cvr/cvn100. Epub 2008 Apr 22. PMID: 18430749 Free PMC Article<br />
9:Maintenance of intercellular coupling by the antiarrhythmic peptide rotigaptide suppresses arrhythmogenic discordant alternans. Kj&oslash;lbye AL, Dikshteyn M, Eloff BC, Desch&ecirc;nes I, Rosenbaum DS.Am J Physiol Heart Circ Physiol. 2008 Jan;294(1):H41-9. Epub 2007 Nov 2. PMID: 17982010 Free Article<br />
10:Pharmacological modulation of gap junction function with the novel compound rotigaptide: a promising new principle for prevention of arrhythmias. Kj&oslash;lbye AL, Haugan K, Hennan JK, Petersen JS.Basic Clin Pharmacol Toxicol. 2007 Oct;101(4):215-30. Review. PMID: 17845503 Free Article

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