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Omiganan Pentahydrochloride

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CAT#
10-101-93
Synonyms/Alias
omiganan pentahydrochloride; MBI-226; MBI226; MBI 226
CAS No.
269062-93-3
Sequence
L-Lysinamide,L-isoleucyl-L-leucyl-L-arginyl-L-tryptophyl-L-prolyl-L-tryptophyl-L-tryptophyl-L-prolyl-L-tryptophyl-L-arginyl-L-arginyl-,hydrochloride (1:5)
M.W/Mr.
1961.45
Molecular Formula
C90H127N27O12·5HCl
Source
Synthetic
Long-term Storage Conditions
−20°C
Application
Omiganan pentahydrochloride, a bactericidal and fungicidal cationic peptide being developed as a topical gel for prevention of catheter-associated infections, inhibited commonly occurring fungal pathogens.
Description
Omiganan Pentahydrochloride (MBI 226), a Topical 12-Amino-Acid Cationic Peptide, has good antimicrobial activity and bactericidal activity.
Areas of Interest
Antimicrobial
  • Background
  • Related Products
  • References

omiganan pentahydrochloride, a pentahydrochloride salt of omiganan, is a synthetic cationic antimicrobial peptide with wide-spectrum activity against both gram-positive and gram-negative bacteria and fungi. Omiganan pentahydrochloride, an analog of indolicidin, acts by disrupting bacterial cytoplasmic membranes and has been tested in a topical gel for the prevention of catheter-related bloodstream infections.

CAS: 616-91-1
Sequence: Ac-Cys-OH
M.W: 163.2
Molecular Formula: ---
CAS: 75921-69-6 (net)
Sequence: Ac-Ser-Tyr-Ser-Nle-Glu-His-D-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2 acetate salt
M.W: 1646.85
Molecular Formula: C78H111N21O19
CAS: 79561-22-1
Sequence: Pyr-His-Trp-Ser-Tyr-D-Ala-Leu-Arg-Pro-NHEt
M.W: 1167.3
Molecular Formula: C56H78N16O12
CAS: 128270-60-0 (net)
Sequence: H-D-Phe-Pro-Arg-Pro-Gly-Gly-Gly-Gly-Asn-Gly-Asp-Phe-Glu-Glu-Ile-Pro-Glu-Glu-Tyr-Leu-OH trifluoroacetate salt
M.W: 2108.3
Molecular Formula: C98H138N24O33

The activity of omiganan pentahydrochloride (formerly MBI 226; a synthetic cationic peptide) was assessed against 1,437 recent clinical bacterial isolates and 214 recent clinical yeast isolates. The omiganan was highly active, and minimal bactericidal concentrations or minimal fungicidal concentrations were either equal to or two- to fourfold higher than MICs. Kill curve experiments showed a clear pattern of bactericidal activity.

Sader, H. S., Fedler, K. A., Rennie, R. P., Stevens, S., & Jones, R. N. (2004). Omiganan pentahydrochloride (MBI 226), a topical 12-amino-acid cationic peptide: spectrum of antimicrobial activity and measurements of bactericidal activity. Antimicrobial agents and chemotherapy, 48(8), 3112-3118.

Omiganan pentahydrochloride is a cidal cationic peptide with a broad antimicrobial spectrum, including yeast, currently in development as a topical agent for the prevention of catheter-associated infections. We evaluated the spectrum and potency of omiganan against pathogens commonly associated with such infections.

Fritsche, T. R., Rhomberg, P. R., Sader, H. S., & Jones, R. N. (2008). Antimicrobial activity of omiganan pentahydrochloride tested against contemporary bacterial pathogens commonly responsible for catheter-associated infections. Journal of antimicrobial chemotherapy.

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.

Melo, M. N., Dugourd, D., & Castanho, M. A. (2006). Omiganan pentahydrochloride in the front line of clinical applications of antimicrobial peptides. Recent patents on anti-infective drug discovery, 1(2), 201-207.

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