rotigaptide   Click here for help

GtoPdb Ligand ID: 9214

Synonyms: Dipeptide 9f [PMID 19175320] | GAP-134 | ZP-123
Compound class: Peptide or derivative
Comment: Rotigaptide is a hexapeptide developed originally by Wyeth, as an anti-arrhythmic agent. It promotes electrical coupling between ventricular myocytes by increasing gap junction conductance [1]. A recent study showed reduction in myocardial infarction size in a porcine model and protection from IRI-related endothelial dysfunction in man. Rotigaptide may thus have therapeutic potential in the treatment of myocardial infarction [2].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OC1CC(N(C1)C(=O)C1CCCN1C(=O)C(Cc1ccc(cc1)O)NC(=O)C)C(=O)NCC(=O)NC(C(=O)NCC(=O)N)C
Isomeric SMILES O[C@H]1C[C@@H](N(C1)C(=O)[C@H]1CCCN1C(=O)[C@@H](Cc1ccc(cc1)O)NC(=O)C)C(=O)NCC(=O)N[C@@H](C(=O)NCC(=O)N)C
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
InChI Key GFJRASPBQLDRRY-TWTQBQJDSA-N
References
1. Butera JA, Larsen BD, Hennan JK, Kerns E, Di L, Alimardanov A, Swillo RE, Morgan GA, Liu K, Wang Q et al.. (2009)
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, 52 (4): 908-11. [PMID:19175320]
2. Pedersen CM, Venkatasubramanian S, Vase H, Hyldebrandt JA, Contractor H, Schmidt MR, Bøtker HE, Cruden NL, Newby DE, Kharbanda RK et al.. (2016)
Rotigaptide protects the myocardium and arterial vasculature from ischaemia reperfusion injury.
Br J Clin Pharmacol, 81 (6): 1037-45. [PMID:26750458]