Omiganan free base

For research use only. Not for therapeutic Use.

  • CAT Number: I033872
  • CAS Number: 204248-78-2
  • Molecular Formula: C90H127N27O12
  • Molecular Weight: 1779.18
  • Purity: 98%
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Omiganan Free Base(Cat No.:I033872)is a synthetic antimicrobial peptide derived from indolicidin, designed for topical use against a range of pathogens, including gram-positive and gram-negative bacteria and fungi. It disrupts microbial cell membranes, leading to rapid cell death, making it effective for managing skin infections and preventing infections in wounds and catheter sites. Known for its low toxicity and stability, Omiganan is particularly valuable in treating antibiotic-resistant infections. Currently under investigation in clinical trials, it holds promise as a safe and effective alternative to traditional antibiotics in dermatological and wound care.


Catalog Number I033872
CAS Number 204248-78-2
Synonyms

Omiganan Free Base

Molecular Formula C90H127N27O12
Purity 98%
Target Bacterial
Solubility To be determined
Appearance Solid powder
Storage Store at -20°C
IUPAC Name (S)-1-(L-isoleucyl-L-leucyl-L-arginyl-L-tryptophyl)-N-((S)-1-(((S)-1-((S)-2-(((S)-1-(((S)-1-(((S)-1-(((S)-1,6-diamino-1-oxohexan-2-yl)amino)-5-guanidino-1-oxopentan-2-yl)amino)-5-guanidino-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
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
InChIKey MVPAMLBUDIFYGK-BHDRXCTLSA-N
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
Reference

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4: Lorenzi T, Trombettoni MMC, Ghiselli R, Paolinelli F, Gesuita R, Cirioni O, Provinciali M, Kamysz W, Kamysz E, Piangatelli C, Castellucci M, Guerrieri M, Morroni M. Effect of omiganan on colonic anastomosis healing in a rat model of peritonitis. Am J Transl Res. 2017 Jul 15;9(7):3374-3386. PMID: 28804554; PMCID: PMC5553886.
5: Niemeyer-van der Kolk T, Assil S, Buters TP, Rijsbergen M, Klaassen ES, Feiss G, Florencia E, Prens EP, Burggraaf J, van Doorn MBA, Rissmann R, Moerland M. Omiganan Enhances Imiquimod-Induced Inflammatory Responses in Skin of Healthy Volunteers. Clin Transl Sci. 2020 May;13(3):573-579. doi: 10.1111/cts.12741. Epub 2020 Feb 13. PMID: 32043302; PMCID: PMC7214655.
6: Niemeyer-van der Kolk T, van der Wall H, Hogendoorn GK, Rijneveld R, Luijten S, van Alewijk DCJG, van den Munckhof EHA, de Kam ML, Feiss GL, Prens EP, Burggraaf J, Rissmann R, van Doorn MBA. Pharmacodynamic Effects of Topical Omiganan in Patients With Mild to Moderate Atopic Dermatitis in a Randomized, Placebo-Controlled, Phase II Trial. Clin Transl Sci. 2020 Sep;13(5):994-1003. doi: 10.1111/cts.12792. Epub 2020 May 1. PMID: 32315497; PMCID: PMC7485951.
7: Septimus EJ, Schweizer ML. Decolonization in Prevention of Health Care- Associated Infections. Clin Microbiol Rev. 2016 Apr;29(2):201-22. doi: 10.1128/CMR.00049-15. PMID: 26817630; PMCID: PMC4786886.
8: van der Kolk TN, Buters TP, Krouwels L, Boltjes J, de Kam ML, van der Wall H, van Alewijk DCJG, van den Munckhof EHA, Becker MJ, Feiss G, Florencia EF, Prens EP, Moerland M, Burggraaf J, Rissmann R, van Doorn MBA. Topical anti-microbial peptide omiganan recovers cutaneous dysbiosis but does not improve clinical symptoms in patients with mild-to-moderate atopic dermatitis in a phase 2 randomized controlled trial. J Am Acad Dermatol. 2020 Sep 30:S0190-9622(20)32659-1. doi: 10.1016/j.jaad.2020.08.132. Epub ahead of print. PMID: 33010325.
9: Ng SMS, Teo SW, Yong YE, Ng FM, Lau QY, Jureen R, Hill J, Chia CSB. Preliminary investigations into developing all-D Omiganan for treating Mupirocin-resistant MRSA skin infections. Chem Biol Drug Des. 2017 Dec;90(6):1155-1160. doi: 10.1111/cbdd.13035. Epub 2017 Jul 11. PMID: 28581672.
10: Rijsbergen M, Rijneveld R, Todd M, Feiss GL, Kouwenhoven STP, Quint KD, van Alewijk DCJG, de Koning MNC, Klaassen ES, Burggraaf J, Rissmann R, van Poelgeest MIE. Results of phase 2 trials exploring the safety and efficacy of omiganan in patients with human papillomavirus-induced genital lesions. Br J Clin Pharmacol. 2020 Nov;86(11):2133-2143. doi: 10.1111/bcp.14181. Epub 2020 Sep 28. PMID: 31755993; PMCID: PMC7576619.

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