10225. Omiganan

Nomenclature

CAS number: 204248-78-2
l-Isoleucyl-l-leucyl-l-arginyl-l-tryptophyl-l-prolyl-l-tryptophyl-l-tryprophyl-l-prolyl-l-tryptophyl-l-arginyl-l-arginyl-l-lysinamide.
C90H127N27O12; mol wt 1779.15.
C 60.76%, H 7.19%, N 21.26%, O 10.79%.

Description and references

Cationic antimicrobial peptide. Synthetic analog of indolicidin, q.v., an antimicrobial peptide isolated from bovine neutrophils. Prepn: J. R. Fraser et al., WO 9807745; eidem, US 6538106 (1998, 2003 both to Micrologix). Comparative in vitro antibacterial spectrum: H. S. Sader et al., Antimicrob. Agents Chemother. 48, 3112 (2004) DOI PubMed. Interaction with bacterial membranes and cell wall models: M. N. Melo, M. A. R. B. Castanho, Biochim. Biophys. Acta 1768, 1277 (2007) DOI PubMed. Review of clinical development: R. E. Isaacson, Curr. Opin. Investig. Drugs 4, 999-1003 (2003) PubMed.

Chemical structure

Derivative

Pentahydrochloride.

Nomenclature

CAS number: 269062-93-3
MBI-226; Omigard (Cadence).
C90H127N27O12.5HCl; mol wt 1961.45.
C 55.11%, H 6.78%, N 19.28%, O 9.79%, Cl 9.04%.

Properties

Molar extinction coefficient at 280 nm: 1.72 × 104.

Therapeutic Category

Antibacterial.

Keywords

Antibacterial (Synthetic); Peptides