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omiganan   Click here for help

GtoPdb Ligand ID: 14110

Synonyms: CLS001 | MBI 226
Compound class: Peptide
Comment: Omiganan is an analogue of indolicidin and a member of the cathelicidin family of antimicrobial peptides. Omiganan demonstrates antibacterial activity against both against Gram-negative and Gram-positive bacteria [2-3] and also has antifungal activity [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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC[C@H](C)[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC4=CNC5=C4C=CC=C5)C(=O)N[C@@H](CC6=CNC7=C6C=CC=C7)C(=O)N8CCC[C@H]8C(=O)N[C@@H](CC9=CNC%10=C9C=CC=C%10)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N)N
Isomeric SMILES CC[C@H](C)[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC4=CNC5=CC=CC=C54)C(=O)N[C@@H](CC6=CNC7=CC=CC=C76)C(=O)N8CCC[C@H]8C(=O)N[C@@H](CC9=CNC%10=CC=CC=C%109)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](CCCCN)C(=O)N)N
InChI InChI=1S/C90H127N27O12/c1-5-51(4)75(92)85(127)113-68(41-50(2)3)80(122)109-67(32-18-38-102-90(98)99)79(121)114-71(44-54-48-105-62-27-12-8-23-58(54)62)86(128)116-39-19-34-74(116)84(126)112-70(43-53-47-104-61-26-11-7-22-57(53)61)82(124)115-72(45-55-49-106-63-28-13-9-24-59(55)63)87(129)117-40-20-33-73(117)83(125)111-69(42-52-46-103-60-25-10-6-21-56(52)60)81(123)110-66(31-17-37-101-89(96)97)78(120)108-65(30-16-36-100-88(94)95)77(119)107-64(76(93)118)29-14-15-35-91/h6-13,21-28,46-51,64-75,103-106H,5,14-20,29-45,91-92H2,1-4H3,(H2,93,118)(H,107,119)(H,108,120)(H,109,122)(H,110,123)(H,111,125)(H,112,126)(H,113,127)(H,114,121)(H,115,124)(H4,94,95,100)(H4,96,97,101)(H4,98,99,102)/t51-,64-,65-,66-,67-,68-,69-,70-,71-,72-,73-,74-,75-/m0/s1
InChI Key MVPAMLBUDIFYGK-BHDRXCTLSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
For clinical application omiganan is formulated as a topical gel containing the pentahydrochloride salt. It has completed a number of Phase 3 studies that evaluated efficacy in the prevention of catheter-related infections and treatment of acne and rosacea.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02576847 Study to Evaluate the Long-term Safety of a Once-Daily Omiganan Topical Gel Phase 3 Interventional Maruho Co., Ltd.
NCT02547441 Study to Evaluate the Safety and Efficacy of a Once-Daily CLS001 Topical Gel Versus Vehicle Phase 3 Interventional Maruho Co., Ltd.
NCT02576860 Study to Evaluate the Safety and Efficacy of a Once-Daily CLS001 Topical Gel Versus Vehicle Phase 3 Interventional Maruho Co., Ltd.
NCT00231153 Study of Omiganan 1% Gel in Preventing Catheter Infections/Colonization in Patients With Central Venous Catheters Phase 3 Interventional Cadence
NCT00027248 Safety and Efficacy of MBI 226 for the Prevention of Central Venous Catheter-Related Bloodstream Infections Phase 3 Interventional BioWest Therapeutics Inc