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Brilacidin information


Brilacidin
Clinical data
Trade namesNone as of July 2012[1]
ATC code
  • none
Identifiers
IUPAC name
  • N,N'-bis[3-{[5-(carbamimidoylamino)pentanoyl]amino}-2-[(3R)-pyrrolidin-3-yloxy]-5-(trifluoromethyl)phenyl]pyrimidine-4,6-dicarboxamide[1]
CAS Number
  • 1224095-98-0
PubChem CID
  • 25023695
ChemSpider
  • 28651526
UNII
  • I1679X069H
KEGG
  • D10414
ChEMBL
  • ChEMBL2219413
CompTox Dashboard (EPA)
  • DTXSID90153594 Edit this at Wikidata
Chemical and physical data
FormulaC40H50F6N14O6
Molar mass936.922 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • C1CNC[C@@H]1OC2=C(C=C(C=C2NC(=O)C3=CC(=NC=N3)C(=O)NC4=CC(=CC(=C4O[C@@H]5CCNC5)NC(=O)CCCCNC(=N)N)C(F)(F)F)C(F)(F)F)NC(=O)CCCCNC(=N)N
InChI
  • InChI=1S/C40H50F6N14O6/c41-39(42,43)21-13-25(57-31(61)5-1-3-9-53-37(47)48)33(65-23-7-11-51-18-23)27(15-21)59-35(63)29-17-30(56-20-55-29)36(64)60-28-16-22(40(44,45)46)14-26(34(28)66-24-8-12-52-19-24)58-32(62)6-2-4-10-54-38(49)50/h13-17,20,23-24,51-52H,1-12,18-19H2,(H,57,61)(H,58,62)(H,59,63)(H,60,64)(H4,47,48,53)(H4,49,50,54)/t23-,24-/m1/s1
  • Key:QPDYBCZNGUJZDK-DNQXCXABSA-N

Brilacidin (formerly PMX-30063[2]), an investigational new drug, is a polymer-based antibiotic currently in human clinical trials, and represents a new class of antibiotics called host defense protein mimetics, or HDP-mimetics, which are non-peptide synthetic small molecules modeled after host defense peptides (HDPs).[3][4][5] HDPs, also called antimicrobial peptides, some of which are defensins, are part of the innate immune response and are common to most higher forms of life.[6][7] As brilacidin is modeled after a defensin, it is also called a defensin mimetic.[citation needed]

Brilacidin is an antibiotic that works by disrupting bacterial cell membranes, mimicking defensins that play a role in innate immunity.[8][9] Several mimics of antimicrobial peptides, both peptides and non-peptides, have been studied, but none have overcome difficulties to reach the market.

  1. ^ a b "Statement on a nonproprietary name adopted by the USAN council" (PDF). American Medical Association. 25 July 2012. {{cite journal}}: Cite journal requires |journal= (help)
  2. ^ "Fact Sheet" (PDF). PolyMedix. Archived from the original (PDF) on 4 March 2016. Retrieved 23 April 2015.
  3. ^ Palermo EF (2011). "Antimicrobial Polymers: peptide-mimetic design and mechanism of action" (PDF). University of Michigan Library.
  4. ^ Palermo EF (2011). "The convergence of peptide and polymer science toward novel antibiotics" (PDF). University of Michigan Library. 158pages
  5. ^ Sgolastra F. "Design and synthesis of biomimetic compounds with pharmacological activity" (PDF). Universita' Politecnica Delle Marche.
  6. ^ Kuroda K, Caputo GA (2013). "Antimicrobial polymers as synthetic mimics of host-defense peptides". Wiley Interdisciplinary Reviews. Nanomedicine and Nanobiotechnology. 5 (1): 49–66. doi:10.1002/wnan.1199. hdl:2027.42/94848. PMID 23076870.
  7. ^ "Designing mimics of membrane active proteins" (PDF). Accounts of Chemical Research
  8. ^ "brilacidin (formerly PMX-30063)". BioCentury BCIQ. BioCentury Publications. Retrieved 19 September 2013.
  9. ^ Butler MS, Cooper MA (June 2011). "Antibiotics in the clinical pipeline in 2011". The Journal of Antibiotics. 64 (6): 413–25. doi:10.1038/ja.2011.44. PMID 21587262.

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