Viomycin

Viomycin
Clinical data
Routes of
administration		Intramuscular injection
Drug classAminoglycoside
ATC code
  • None
Legal status
Legal status
Identifiers
  • (S)-3,6-Diamino-N-((3S,9S,12S,15S,Z)-((2R,4S)-6-amino-4-hydroxy-1,2,3,4-tetrahydropyridin-2-yl)-9,12-bis(hydroxymethyl)2,5,8,11,14-pentaoxo-6-(ureidomethylene)-1,4,7,10,13-pentaazacyclohexadecan-15-yl)hexanamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.046.643 Edit this at Wikidata
Chemical and physical data
FormulaC25H43N13O10
Molar mass685.700 g·mol−1
3D model (JSmol)
  • C1[C@@H](NC(=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=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 checkY
  • Key:GXFAIFRPOKBQRV-GHXCTMGLSA-N checkY
  • Key:AQONYROJHRNYQQ-QMAPKBLTSA-N
 ☒NcheckY (what is this?)  (verify)

Viomycin is a member of the tuberactinomycin family,[1][2][3] a group of nonribosomal peptide antibiotics exhibiting anti-tuberculosis activity. The tuberactinomycin family is an essential component in the drug cocktail currently used to fight infections of Mycobacterium tuberculosis. Viomycin was the first member of the tuberactinomycins to be isolated and identified,[4] and was used to treat TB until it was replaced by the less toxic, but structurally related compound, capreomycin. The tuberactinomycins target bacterial ribosomes, binding RNA and disrupting bacterial protein synthesis and certain forms of RNA splicing. Viomycin is produced by the actinomycete Streptomyces puniceus.[5]

  1. ^ Bycroft BW (1972). "The crystal structure of viomycin, a tuberculostatic antibiotic". Chem. Commun. (11): 660. doi:10.1039/c39720000660.
  2. ^ Noda T, Take T, Nagata A, Wakamiya T, Shiba T (July 1972). "Chemical studies on tuberactinomycin. 3. The chemical structure of viomycin (tuberactinomycin B)". The Journal of Antibiotics. 25 (7): 427–8. doi:10.7164/antibiotics.25.427. PMID 4350196.
  3. ^ Kitagawa T, Miura T, Fujiwara K, Taniyama H (October 1972). "The total structure of viomycin by sequential analysis". Chemical & Pharmaceutical Bulletin. 20 (10): 2215–25. doi:10.1248/cpb.20.2215. PMID 4346588.
  4. ^ Barkei JJ, Kevany BM, Felnagle EA, Thomas MG (January 2009). "Investigations into viomycin biosynthesis by using heterologous production in Streptomyces lividans". ChemBioChem. 10 (2): 366–76. doi:10.1002/cbic.200800646. PMC 2765823. PMID 19105177.
  5. ^ Hutchings MI, Truman AW, Wilkinson B (October 2019). "Antibiotics: past, present and future". Current Opinion in Microbiology. 51: 72–80. doi:10.1016/j.mib.2019.10.008. PMID 31733401.