WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 414569
CAS#: 204248-78-2 (free base)
Description: Omiganan Free Base is used for treatment of Mupirocin-resistant MRSA skin infections.
MedKoo Cat#: 414569
Name: Omiganan Free Base
CAS#: 204248-78-2 (free base)
Chemical Formula: C90H127N27O12
Exact Mass: 1778.0158
Molecular Weight: 1779.18
Elemental Analysis: C, 60.76; H, 7.20; N, 21.26; O, 10.79
This product is not in stock, which may be available by custom synthesis.
For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge).
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Related CAS #: 204248-78-2 (free base) 269062-93-3 (pentahydrochloride)
Synonym: Omiganan Free Base
IUPAC/Chemical 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 Key: MVPAMLBUDIFYGK-BHDRXCTLSA-N
InChi Code: 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
SMILES Code: CC[C@@H]([C@@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N1CCC[C@H]1C(N[C@H](C(N[C@H](C(N2CCC[C@H]2C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N)=O)CCCCN)=O)CCCNC(N)=N)=O)CCCNC(N)=N)=O)Cc(c[nH]3)c4c3cccc4)=O)=O)Cc(c[nH]5)c6c5cccc6)=O)Cc(c[nH]7)c8c7cccc8)=O)=O)Cc(c[nH]9)c%10c9cccc%10)=O)CCCNC(N)=N)=O)CC(C)C)=O)N)C
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 1779.18 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
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.
