Compound ID | 1843

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Capreomycin

Class: Natural product antibiotic

Agent Type: Natural product; Direct acting;
Spectrum of activity: Antimycobacterial
Mechanism of action: Protein synthesis inhibitor. Stabilises peptidyl-tRNA in the pretranslocation complex, preventing translocation of the ribosome along the mRNA
Target Pathogen: Active against Mycobacterium spp.
Description: Streptomyces natural product; rarely used as alternative for multidrug resistant tuberculosis in combination; administered intravenously or in aerosol form; tuberactinomycin-type antibiotic (cyclic peptide often grouped with aminoglycoside)
Year first mentioned: 1960
Highest development stage: Approved by FDA in 1971
Development status: Withdrawn
Reason dropped: Poses health risks such as ear toxicity (ototoxicity), hearing loss, and kidney dysfunction (nephrotoxicity)
Chemical structure(s):
Click here for structure editor
Molecular weight: 1321.41
Iso. SMILES: C[C@H]1C(=O)N[C@H](C(=O)N/C(=C/NC(=O)N)/C(=O)N[C@H](C(=O)NC[C@@H](C(=O)N1)N)[C@H]2CCN=C(N2)N)CNC(=O)C[C@H](CCCN)N.C1CN=C(N[C@H]1[C@H]2C(=O)NC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N/C(=C/NC(=O)N)/C(=O)N2)CNC(=O)C[C@H](CCCN)N)CO)N)N
InChI Key: VCOPTHOUUNAYKQ-WBTCAYNUSA-N
Can. SMILES: C(C[C@@H](CC(=O)NC[C@H]1C(=O)N/C(=C/NC(=O)N)/C(=O)N[C@@H]([C@H]2CCN=C(N)N2)C(=O)NC[C@@H](C(=O)N[C@@H](CO)C(=O)N1)N)N)CN.C[C@H]1C(=O)N[C@@H](CNC(=O)C[C@H](CCCN)N)C(=O)N/C(=C/NC(=O)N)/C(=O)N[C@@H]([C@H]2CCN=C(N)N2)C(=O)NC[C@@H](C(=O)N1)N
InChI: InChI=1S/C25H44N14O8.C25H44N14O7/c26-4-1-2-11(27)6-17(41)32-8-14-20(43)35-15(9-34-25(30)47)21(44)39-18(13-3-5-31-24(29)38-13)23(46)33-7-12(28)19(42)37-16(10-40)22(45)36-14;1-11-19(41)36-15(9-32-17(40)7-12(27)3-2-5-26)21(43)37-16(10-34-25(30)46)22(44)39-18(14-4-6-31-24(29)38-14)23(45)33-8-13(28)20(42)35-11/h9,11-14,16,18,40H,1-8,10,26-28H2,(H,32,41)(H,33,46)(H,35,43)(H,36,45)(H,37,42)(H,39,44)(H3,29,31,38)(H3,30,34,47);10-15,18H,2-9,26-28H2,1H3,(H,32,40)(H,33,45)(H,35,42)(H,36,41)(H,37,43)(H,39,44)(H3,29,31,38)(H3,30,34,46)/b15-9+;16-10+/t11-,12-,13+,14-,16-,18-;11-,12-,13-,14+,15-,18-/m00/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/3000502
Guide to Pharmacology: capreomycin IB
Citations:
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5960728/
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3187005/

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