Omiganan Pentahydrochloride
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Omiganan Pentahydrochloride

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Omiganan is a synthetic cationic antimicrobial peptide with wide-spectrum activity against both gram-positive and gram-negative bacteria.

Category
Functional Peptides
Catalog number
BAT-006195
CAS number
269062-93-3
Molecular Formula
C90H132Cl5N27O12
Molecular Weight
1961.4
Omiganan Pentahydrochloride
Size Price Stock Quantity
5 mg $298 In stock
IUPAC Name
1-[2-[[2-[[2-[(2-amino-3-methylpentanoyl)amino]-4-methylpentanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]-N-[1-[[1-[2-[[1-[[5-carbamimidamido-1-[[5-carbamimidamido-1-[(1,6-diamino-1-oxohexan-2-yl)amino]-1-oxopentan-2-yl]amino]-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]carbamoyl]pyrrolidin-1-yl]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pyrrolidine-2-carboxamide;pentahydrochloride
Synonyms
MBI 226; MBI-226; MBI226; Omiganan HCl
Appearance
White Powder
Purity
98%
Sequence
XLRWPWWPWRRK
Storage
Store at -20°C
InChI
InChI=1S/C90H127N27O12.5ClH/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);5*1H
InChI Key
WTNSIKUBZJCPLJ-IQOWARLESA-N
Canonical SMILES
CCC(C)C(C(=O)NC(CC(C)C)C(=O)NC(CCCNC(=N)N)C(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)N3CCCC3C(=O)NC(CC4=CNC5=CC=CC=C54)C(=O)NC(CC6=CNC7=CC=CC=C76)C(=O)N8CCCC8C(=O)NC(CC9=CNC1=CC=CC=C19)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCNC(=N)N)C(=O)NC(CCCCN)C(=O)N)N.Cl.Cl.Cl.Cl.Cl
1. Omiganan pentahydrochloride in the front line of clinical applications of antimicrobial peptides
Miguel A R B Castanho, Dominique Dugourd, Manuel N Melo Recent Pat Antiinfect Drug Discov . 2006 Jun;1(2):201-7. doi: 10.2174/157489106777452638.
Ribosomally synthesized antimicrobial peptides have very wide killing spectra and bacterial resistance to these peptides seems to be a rare phenomenon. Indolicidin is a ribosomally synthesized antimicrobial peptide that served as a template to omiganan, which is in development for the prevention of catheter-related bloodstream infections; clinical trials also proved its efficiency against acne vulgaris. Omiganan is the most advanced molecule in the front line of clinical applications of antimicrobial peptides. The mode and site of action of omiganan are not yet settled although its interaction with membranes is known to play a fundamental role. The biochemical and biophysical foundations for the action of indolicidin and its analogues are reviewed in this paper, as well as the clinical application of omiganan. The in vitro efficiency tests and the outcome of clinical trials are addressed. Altogether, despite the very specific use of omiganan as a topical antibiotic, it has the potential of being a pioneer of a new generation of antibiotics that carry the promise of ending the multi-resistance problem.
2. Mupirocin resistance: clinical implications and potential alternatives for the eradication of MRSA
T Poovelikunnel, G Gethin, H Humphreys J Antimicrob Chemother . 2015 Oct;70(10):2681-92. doi: 10.1093/jac/dkv169.
Mupirocin 2% ointment is used either alone or with skin antiseptics as part of a comprehensive MRSA decolonization strategy. Increased mupirocin use predisposes to mupirocin resistance, which is significantly associated with persistent MRSA carriage. Mupirocin resistance as high as 81% has been reported. There is a strong association between previous mupirocin exposure and both low-level and high-level mupirocin resistance. High-level mupirocin resistance (mupA carriage) is also linked to MDR. Among MRSA isolates, the presence of the qacA and/or qacB gene, encoding resistance to chlorhexidine, ranges from 65% to 91%, which, along with mupirocin resistance, is associated with failed decolonization. This is of significant concern for patient care and infection prevention and control strategies as both these agents are used concurrently for decolonization. Increasing bacterial resistance necessitates the discovery or development of new antimicrobial therapies. These include, for example, polyhexanide, lysostaphin, ethanol, omiganan pentahydrochloride, tea tree oil, probiotics, bacteriophages and honey. However, few of these have been evaluated fully or extensively tested in clinical trials and this is required to in part address the implications of mupirocin resistance.
3. Antimicrobial activity of omiganan pentahydrochloride against contemporary fungal pathogens responsible for catheter-associated infections
Paul R Rhomberg, Thomas R Fritsche, Ronald N Jones, Helio S Sader Antimicrob Agents Chemother . 2008 Mar;52(3):1187-9. doi: 10.1128/AAC.01475-07.
Omiganan, a bactericidal and fungicidal cationic peptide being developed as a topical gel for prevention of catheter-associated infections, inhibited commonly occurring fungal pathogens including Candida spp. (106 isolates) at
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