Compound ID | 2020

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Polymyxin B

Class: Polymyxin

Agent Type: Natural product; Direct acting;
Spectrum of activity: Gram-negative
Mechanism of action: Membrane-active agent. Disrupts the outer membrane by direct interaction with the lipid A component of the LPS and disrupts the physical integrity of the phospholipid bilayer of the inner membrane.
Target Pathogen: Active against Gram-negative bacteria including Acinetobacter and Pseudomonas
Description: Natural product produced by Paenibacillus polymyxa. Polymyxin B is composed of polymyxins B1, B1-I, B2, B3, and B6. Used for systemic and topical treatment of Gram-negative infections.
Year first mentioned: 1947
Highest development stage: Approved by FDA
Development status: Approved
Chemical structure(s):
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Molecular weight: 1301.56
Iso. SMILES: CCC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CCN)CC2=CC=CC=C2)CC(C)C)CCN)CCN)C(C)O.OS(=O)(=O)O
InChI Key: HFMDLUQUEXNBOP-UHFFFAOYSA-N
Can. SMILES: CCC(C)CCCCC(=O)NC(CCN)C(=O)NC(C(C)O)C(=O)NC(CCN)C(=O)NC1CCNC(=O)C(C(C)O)NC(=O)C(CCN)NC(=O)C(CCN)NC(=O)C(CC(C)C)NC(=O)C(CC2=CC=CC=C2)NC(=O)C(CCN)NC1=O.OS(=O)(=O)O
InChI: InChI=1S/C56H98N16O13.H2O4S/c1-7-32(4)13-11-12-16-44(75)63-36(17-23-57)51(80)72-46(34(6)74)56(85)68-39(20-26-60)48(77)67-41-22-28-62-55(84)45(33(5)73)71-52(81)40(21-27-61)65-47(76)37(18-24-58)66-53(82)42(29-31(2)3)69-54(83)43(30-35-14-9-8-10-15-35)70-49(78)38(19-25-59)64-50(41)79;1-5(2,3)4/h8-10,14-15,31-34,36-43,45-46,73-74H,7,11-13,16-30,57-61H2,1-6H3,(H,62,84)(H,63,75)(H,64,79)(H,65,76)(H,66,82)(H,67,77)(H,68,85)(H,69,83)(H,70,78)(H,71,81)(H,72,80);(H2,1,2,3,4)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5702105
Guide to Pharmacology: polymyxin B
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/34954369/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8941995/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7911091/

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