murepavadin   Click here for help

GtoPdb Ligand ID: 10832

Synonyms: POL7080 | RG-7929 | RG7929 | RO-7033877 | RO7033877
Compound class: Peptide or derivative
Comment: Murepavadin is a cyclic β hairpin peptidomimetic based on the cationic antimicrobial peptide protegrin I. It targets the outer membrane of Gram-negative pathogens [1].
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 NCCC[C@@H]1NC(=O)[C@H](CCN)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]2CCCN2C(=O)[C@H]2CCCN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC1=O)CCN)CCN)Cc1c[nH]c2c1cccc2)CCN)CCN)C)CO)[C@H](O)C)Cc1c[nH]c2c1cccc2)[C@H](CC)C
Isomeric SMILES NCCC[C@@H]1NC(=O)[C@H](CCN)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]2CCCN2C(=O)[C@H]2CCCN2C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC1=O)CCN)CCN)Cc1c[nH]c2c1cccc2)CCN)CCN)C)CO)[C@H](O)C)Cc1c[nH]c2c1cccc2)[C@H](CC)C
InChI InChI=1S/C73H112N22O16/c1-5-38(2)58-70(108)88-52(24-30-79)65(103)83-47(17-10-25-74)62(100)85-49(21-27-76)63(101)86-51(23-29-78)66(104)89-53(33-41-35-80-45-15-8-6-13-43(41)45)67(105)87-50(22-28-77)64(102)84-48(20-26-75)61(99)82-39(3)60(98)91-55(37-96)72(110)95-32-12-19-57(95)73(111)94-31-11-18-56(94)69(107)93-59(40(4)97)71(109)90-54(68(106)92-58)34-42-36-81-46-16-9-7-14-44(42)46/h6-9,13-16,35-36,38-40,47-59,80-81,96-97H,5,10-12,17-34,37,74-79H2,1-4H3,(H,82,99)(H,83,103)(H,84,102)(H,85,100)(H,86,101)(H,87,105)(H,88,108)(H,89,104)(H,90,109)(H,91,98)(H,92,106)(H,93,107)/t38-,39-,40+,47-,48-,49+,50-,51-,52-,53-,54-,55-,56-,57+,58-,59-/m0/s1
InChI Key RIDRXGOBXZLKHZ-NZUANIILSA-N
No information available.
Summary of Clinical Use Click here for help
Murepavadin was progressed to clinical evaluation to treat drug-resistant pseudomonal pneumonia [2]. However, Phase 3 studies of Murepavadin for Pseudomonas nocosomial pneumonia were terminated following an interim safety data review which revealed higher than expected acute kidney injury in the murepavadin arm (May 2019).
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT03582007 Pivotal Study in Nosocomial Pneumonia Suspected or Confirmed to be Due to Pseudomonas Phase 3 Interventional Polyphor Ltd.
NCT03409679 Pivotal Study in VAP Suspected or Confirmed to be Due to Pseudomonas Aeruginosa Phase 3 Interventional Polyphor Ltd.