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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H43N13O10
Molecular Weight 685.69
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of VIOMYCIN

SMILES

[H][C@@]1(C[C@H](O)NC(N)=N1)[C@]2([H])NC(=O)\C(NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CNC2=O)NC(=O)C[C@@H](N)CCCN)=C\NC(N)=O

InChI

InChIKey=GXFAIFRPOKBQRV-GHXCTMGLSA-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

HIDE SMILES / InChI

Molecular Formula C25H43N13O10
Molecular Weight 685.69
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 2
Optical Activity UNSPECIFIED

Description

Viomycin is a basic peptide antibiotic, which is among the most effective agents against multidrug-resistant tuberculosis. The tuberactinomycins, such as Viomycin, target bacterial ribosomes, binding RNA and disrupting bacterial protein biosynthesis. Specifically, viomycin binds to a site on the ribosome which lies at the interface between helix 44 of the small ribosomal subunit and helix 69 of the large ribosomal subunit. The structures of this complexes suggest that the viomycin inhibits translocation by stabilizing the tRNA in the A site in the pretranslocation state.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
VIOCIN SULFATE

Cmax

ValueDoseCo-administeredAnalytePopulation
50 μg/mL
1 g single, intramuscular
VIOMYCIN plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
Pulmunary tuberculosis: 30-75 mg/kg, intramuscularly, 14-182 days
Route of Administration: Intramuscular
In Vitro Use Guide
Viomycin at a concentration of 10 uM inhibits E. coli ribosomes to the extent of about 70% as measured in the poly (U) system, and to about 85% in a natural mRNA (R17) system.
Substance Class Chemical
Record UNII
YVU35998K5
Record Status Validated (UNII)
Record Version