Compound ID | 2779

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Viomycin

Synonym(s): Celiomycin  |  florimycin  |  tuberactinomycin B  |  viocin

Class: Natural product antibiotic

Agent Type: Natural product; Small molecule; Direct acting;
Spectrum of activity: Antimycobacterial
Mechanism of action: Protein synthesis inhibitor. Blocks elongation factor G-mediated translocation of mRNA
Target Pathogen: Active against Mycobacterium tuberculosis. Mycobacterium ranae, Mycobacterium phlei, and Mycobacterium smegmatis
Description: Natural product from Streptomyces puniceus; administered via injection; used as second line anti-tubercular drug; a tuberactinomycin-type antibiotic
Institute where first reported: Research Laboratories of Parke, Davis & Company, Detroit Michigan USA; Research Laboratories, Chas. Pfizer & Co., Inc., Brooklyn, New York, USA
Year first mentioned: 1951
Highest development stage: Approved in 1953
Development status: Discontinued
Reason dropped: Availability of safer alternatives; more effective antibiotic alternatives available
Chemical structure(s):
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Molecular weight: 685.69
Iso. SMILES: C1[C@@H](N=C(N[C@H]1O)N)[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)CO)CO)NC(=O)C[C@H](CCCN)N
InChI Key: GXFAIFRPOKBQRV-GHXCTMGLSA-N
Can. SMILES: C(C[C@@H](CC(=O)N[C@H]1CNC(=O)[C@H]([C@H]2C[C@@H](NC(=N2)N)O)NC(=O)/C(=C/NC(=O)N)/NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC1=O)N)CN
InChI: InChI=1S/C25H43N13O10/c26-3-1-2-10(27)4-16(41)32-12-6-30-23(47)18(11-5-17(42)37-24(28)36-11)38-20(44)13(7-31-25(29)48)33-21(45)14(8-39)35-22(46)15(9-40)34-19(12)43/h7,10-12,14-15,17-18,39-40,42H,1-6,8-9,26-27H2,(H,30,47)(H,32,41)(H,33,45)(H,34,43)(H,35,46)(H,38,44)(H3,28,36,37)(H3,29,31,48)/b13-7-/t10-,11+,12-,14-,15-,17-,18-/m0/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/135398671
Guide to Pharmacology: viomycin
Citations:
  • https://www.atsjournals.org/doi/epdf/10.1164/art.1951.63.1.1?role=tab
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4743798/
  • https://www.pnas.org/doi/full/10.1073/pnas.2002888117
  • https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2765823/

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