Compound ID | 1228

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SPR741

Synonym(s): NAB741  |  NAB 741  |  NAB-741  |  SPR-741  |  SPR 741

Class: Polymyxin

Agent Type: Semisynthetic; Small molecule; Direct acting; Antibiotic adjuvant;
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
Combined with other compounds: Yes
Description: Potentiates the activity of rifampin, clarithromycin, azithromycin, mupirocin, fusidic acid and vancomycin against Escherichia coli, Klebsiella pneumoniae and Acinetobacter baumannii but not Pseudomonas aeruginosa
Institute where first reported: Northern Antibiotics, Spero Therapeutics
Highest development stage: Phase 1
Development status: Active
Reason dropped: Replaced by SPR206; developed instead as an antibiotic adjuvant
Chemical structure(s):
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Molecular weight: 992.13
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](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)C)O
InChI Key: JBFNEVNUGGFPBQ-DDMCRLCFSA-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](CO)NC(=O)[C@H]([C@@H](C)O)NC(=O)C
InChI: InChI=1S/C44H73N13O13/c1-22(2)19-31-40(66)52-27(11-15-45)36(62)51-29(13-17-47)39(65)57-34(23(3)59)43(69)48-18-14-30(53-42(68)33(21-58)56-44(70)35(24(4)60)49-25(5)61)38(64)50-28(12-16-46)37(63)55-32(41(67)54-31)20-26-9-7-6-8-10-26/h6-10,22-24,27-35,58-60H,11-21,45-47H2,1-5H3,(H,48,69)(H,49,61)(H,50,64)(H,51,62)(H,52,66)(H,53,68)(H,54,67)(H,55,63)(H,56,70)(H,57,65)/t23-,24-,27+,28+,29+,30+,31+,32-,33-,34+,35+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/53323381
Guide to Pharmacology: SPR741
Citations:
  • https://www.ncbi.nlm.nih.gov/pubmed/28533232
  • https://www.ncbi.nlm.nih.gov/pubmed/28947471
  • https://www.ncbi.nlm.nih.gov/pubmed/29914941

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