Structure via PubChem · Public domain (PubChem)
روتیگاپتید
Sign in to saveAlso known as Dipeptide 9f [PMID 19175320], GAP-134, ZP-123, Rotigaptide
Rotigaptide (ZP-123) is a drug under clinical investigation for the treatment of cardiac arrhythmias – specifically atrial fibrillation. It is a peptide analog that has been shown to increase gap junction intercellular conductance in cardiac muscle cells. Gap junctions are protein channels that are responsible for conducting electrical impulses between cells in the heart to maintain normal rhythm. Gap junction modulation is a promising and novel mechanism of action for the treatment of cardiovascular disorders. Its peptide sequence is Ac-D-Tyr-D-Pro-D-Hyp-Gly-D-Ala-Gly-NH2.
Chemical data
- Formula
- C28H39N7O9
- Molecular weight
- 617.7 g/mol
- 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
- SMILES
- C[C@H](C(=O)NCC(=O)N)NC(=O)CNC(=O)[C@H]1C[C@@H](CN1C(=O)[C@H]2CCCN2C(=O)[C@@H](CC3=CC=C(C=C3)O)NC(=O)C)O
- InChIKey
- GFJRASPBQLDRRY-TWTQBQJDSA-N
- XLogP
- -2.3
- Polar surface area
- 241 Ų
- H-bond donors
- 7
- H-bond acceptors
- 9
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Protein
- Indications
- cardiac arrhythmia
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 617.280926
Show 3 more facts
- chemical formula
- C₂₈H₃₉N₇O₉
- isomeric SMILES
- C[C@H](C(=O)NCC(=O)N)NC(=O)CNC(=O)[C@H]1C[C@@H](CN1C(=O)[C@H]2CCCN2C(=O)[C@@H](CC3=CC=C(C=C3)O)NC(=O)C)O
- canonical 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
Sources (1)
via Wikidata · CC0