Omiganan Free Base

  • 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 peptide antimicrobial agent with broad-spectrum activity against various bacteria. It acts by disrupting microbial cell membranes, leading to their death. Omiganan Free Base has shown potential in treating skin and wound infections, including drug-resistant strains. It is also being studied for its ability to prevent catheter-related bloodstream infections.

Catalog Number I033872
CAS Number 204248-78-2
Molecular Formula

C90H127N27O12

Purity 98
Solubility To be determined
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

1: Cong TX, Hao D, Wen X, Li XH, He G, Jiang X. From pathogenesis of acne vulgaris to anti-acne agents. Arch Dermatol Res. 2019 Jul;311(5):337-349. doi: 10.1007/s00403-019-01908-x. Epub 2019 Mar 11. PMID: 30859308.
2: Grievink HW, Jirka SMG, Woutman TD, Schoonakker M, Rissmann R, Malone KE, Feiss G, Moerland M. Antimicrobial Peptide Omiganan Enhances Interferon Responses to Endosomal Toll-Like Receptor Ligands in Human Peripheral Blood Mononuclear Cells. Clin Transl Sci. 2020 Sep;13(5):891-895. doi: 10.1111/cts.12789. Epub 2020 Apr 21. PMID: 32314872; PMCID: PMC7485948.
3: Melo MN, Dugourd D, Castanho MA. Omiganan pentahydrochloride in the front line of clinical applications of antimicrobial peptides. Recent Pat Antiinfect Drug Discov. 2006 Jun;1(2):201-7. doi: 10.2174/157489106777452638. PMID: 18221145.
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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