Viomycin

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

Class: Tuberactinomycin

Details of activity:	Active against Mycobacterium tuberculosis. Mycobacterium ranae, Mycobacterium phlei, and Mycobacterium smegmatis; protein synthesis inhibitor (blocks elongation factor G-mediated translocation of mRNA)
Description:	Natural product from Streptomyces puniceus; administered via injection; used as second line anti-tubercular drug
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 developmental phase:	Approved in 1953
Development status:	Discontinued

Chemical structure(s):
Canonical 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
Isomeric 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:	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
InChI Key:	GXFAIFRPOKBQRV-GHXCTMGLSA-N
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/135398671

External links:
Guide to Pharmacology:	viomycin
Main Source:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2765823/
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