Compound ID | 2109

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CPZEN-45

Class: Small molecule antibacterial agent

Agent Type: Semisynthetic; Small molecule; Direct acting;
Spectrum of activity: Antimycobacterial
Mechanism of action: Cell wall synthesis inhibitor. Interferes with cell-wall synthesis by inhibiting transfer of the peptidoglycan precursor moiety (MurNAc-pentapeptide) to the membrane lipid carrier, undecaprenyl phosphate; MraY inhibitor
Target Pathogen: Active against Mycobacterium tuberculosis
Description: Semisynthetic caprazamycin; several analogues; applied as inhalation
Institute where first reported: Working Group on New TB Drugs
Year first mentioned: 2008
Highest development stage: Preclinical
Development status: Experimental
Chemical structure(s):
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Molecular weight: 688.73
Iso. SMILES: CCCCC1=CC=C(C=C1)NC(=O)C2=CCN([C@H](C(=O)N2C)[C@@H]([C@@H]3[C@H]([C@H]([C@@H](O3)N4C=CC(=O)NC4=O)O)O)O[C@H]5[C@@H]([C@@H]([C@H](O5)CN)O)O)C
InChI Key: RQVDLVWYEOCAJE-KDHSHZOVSA-N
Can. SMILES: CCCCC1=CC=C(C=C1)NC(=O)C2=CCN(C)[C@@H]([C@@H]([C@@H]3[C@H]([C@H]([C@H](N4C=CC(=O)NC4=O)O3)O)O)O[C@H]5[C@@H]([C@@H]([C@@H](CN)O5)O)O)C(=O)N2C
InChI: InChI=1S/C32H44N6O11/c1-4-5-6-16-7-9-17(10-8-16)34-28(44)18-11-13-36(2)21(29(45)37(18)3)26(49-31-25(43)22(40)19(15-33)47-31)27-23(41)24(42)30(48-27)38-14-12-20(39)35-32(38)46/h7-12,14,19,21-27,30-31,40-43H,4-6,13,15,33H2,1-3H3,(H,34,44)(H,35,39,46)/t19-,21+,22-,23+,24-,25-,26+,27+,30-,31+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/67419859
Guide to Pharmacology: CPZEN-45
Citations:
  • https://pubmed.ncbi.nlm.nih.gov/23919471/
  • https://www.nature.com/articles/ja20139
  • https://www.nature.com/articles/s41429-019-0241-5

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