Compound ID | 730

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CB-182804, CB-182,804

Class: Polymyxin

Spectrum of activity: Gram-negative
Details of activity: Disrupts the membrane integrity by targeting LPS in the cytoplasmic membrane leading to the permeabilization of the bacterial cell. Multiple additional mechnisms are described.
Description: Lower efficiency in mouse septicemia model than polymixin B against Gram negatives but was more tolerable in cynomolgus monkeys
Institute where first reported: Cubist Pharmaceuticals (Merck & Co, USA); BioSource Pharmaceuticals (Spring Valley, NY, USA)
Year first mentioned: 2010
Highest developmental phase: Phase 1
Development status: Inactive
Reason Dropped: Discontinued in 2010 after phase I trials began in 2009 after phase I, seems to be due to nephrotoxicity
Chemical structure(s):
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Molecular weight: 1216.82
Iso. SMILES: C[C@H]([C@H]1C(=O)NCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCN)CCN)CC(C)C)CC2=CC=CC=C2)CCN)NC(=O)[C@H](CCN)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)NC3=CC=CC=C3Cl)O
InChI Key: OINMSSZOBLWDTB-SHGLBBHXSA-N
Can. SMILES: CC(C)C[C@H]1C(=O)N[C@@H](CCN)C(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC[C@@H](C(=O)N[C@@H](CCN)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N1)NC(=O)[C@H](CCN)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)NC3=C(C=CC=C3)Cl
InChI: InChI=1S/C54H86ClN17O13/c1-28(2)26-40-50(81)64-34(14-20-56)44(75)63-37(17-23-59)48(79)71-42(29(3)73)52(83)61-25-19-39(47(78)62-35(15-21-57)46(77)68-41(51(82)67-40)27-31-10-6-5-7-11-31)65-45(76)36(16-22-58)66-53(84)43(30(4)74)72-49(80)38(18-24-60)70-54(85)69-33-13-9-8-12-32(33)55/h5-13,28-30,34-43,73-74H,14-27,56-60H2,1-4H3,(H,61,83)(H,62,78)(H,63,75)(H,64,81)(H,65,76)(H,66,84)(H,67,82)(H,68,77)(H,71,79)(H,72,80)(H2,69,70,85)/t29-,30-,34+,35+,36+,37+,38+,39+,40+,41+,42+,43+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/52918383
Guide to Pharmacology: CB-182804
Citations:
  • https://www.nature.com/articles/ja2016146.pdf?draft=marketing
  • https://www.ncbi.nlm.nih.gov/pubmed/22196342

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