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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

Description
Curator's Comment: Description was created based on several sources, including https://books.google.ru/books?id=JxElBQAAQBAJ&pg=PA421&lpg=PA421&dq=VIOMYCIN retrieved from Antibiotics: Origin, Nature and Properties Tadeusz Korzybski,Zuzanna Kowszyk-Gindifer,Wlodzimierz Kurylowicz, p. 421

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
VIOCIN SULFATE

Approved Use

Viomycin is used to fight infections of Mycobacterium tuberculosis.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
50 μg/mL
1 g single, intramuscular
dose: 1 g
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
VIOMYCIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
15 mg/kg 1 times / day multiple, intravenous
Dose: 15 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 15 mg/kg, 1 times / day
Co-administed with::
pyrazinamide
Sources:
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: tubersulosis
Age Group: 58 years
Sex: M
Population Size: 1
Sources:
Other AEs: Hypomagnesemia, Hypocalcemia...
Other AEs:
Hypomagnesemia
Hypocalcemia
Hypokalemia
Sources:
75 mg/kg 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: tubersulosis
Sources:
Other AEs: Hypocalcemia, Hypokalemia...
AEs

AEs

AESignificanceDosePopulation
Hypocalcemia
15 mg/kg 1 times / day multiple, intravenous
Dose: 15 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 15 mg/kg, 1 times / day
Co-administed with::
pyrazinamide
Sources:
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: tubersulosis
Age Group: 58 years
Sex: M
Population Size: 1
Sources:
Hypokalemia
15 mg/kg 1 times / day multiple, intravenous
Dose: 15 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 15 mg/kg, 1 times / day
Co-administed with::
pyrazinamide
Sources:
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: tubersulosis
Age Group: 58 years
Sex: M
Population Size: 1
Sources:
Hypomagnesemia
15 mg/kg 1 times / day multiple, intravenous
Dose: 15 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 15 mg/kg, 1 times / day
Co-administed with::
pyrazinamide
Sources:
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: tubersulosis
Age Group: 58 years
Sex: M
Population Size: 1
Sources:
Hypocalcemia
75 mg/kg 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: tubersulosis
Sources:
Hypokalemia
75 mg/kg 1 times / day multiple, intravenous
Highest studied dose
Dose: 75 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 75 mg/kg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Condition: tubersulosis
Sources:
PubMed

PubMed

TitleDatePubMed
Experimental studies on therapeutic effects of various combinations of antituberculosis drugs. II. Comparison of various regimens in treatment of experimental mouse tuberculosis infected with SM- and INH-resistant Schacht strain.
1967 Jul
In vitro and in vivo susceptibility of atypical mycobacteria to various drugs.
1981 Sep-Oct
A Bartter's-like syndrome from capreomycin, and a similar gentamicin tubulopathy.
1986 Mar
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production.
1993 Sep 24
Bioluminescence screening in vitro (Bio-Siv) assays for high-volume antimycobacterial drug discovery.
1996 Jun
Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs.
2000 Feb 1
Developing a dynamic pharmacophore model for HIV-1 integrase.
2000 Jun 1
Patents

Sample Use Guides

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.
Name Type Language
VIOMYCIN
INN   WHO-DD  
INN  
Official Name English
CELIOMYCIN
Common Name English
FLORIMYCIN
Common Name English
viomycin [INN]
Common Name English
Viomycin [WHO-DD]
Common Name English
VINACETIN A
Common Name English
GLYCINE, 3-AMINO-N-((3S)-3,6-DIAMINO-1-OXOHEXYL)-L-ALANYL-L-SERYL-L-SERYL-(2Z)-3-((AMINOCARBONYL)AMINO)-2,3-DIDEHYDROALANYL-2-((4R,6S)-2-AMINO-1,4,5,6-TETRAHYDRO-6-HYDROXY-4-PYRIMIDINYL)-, (5->13)-LACTAM, (2S)-
Common Name English
VIOACTANE
Common Name English
TUBERACTINOMYCIN B
MI  
Common Name English
TUBERACTINOMYCIN B [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C280
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
Code System Code Type Description
CHEBI
60081
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
PRIMARY
SMS_ID
100000079138
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
PRIMARY
DRUG CENTRAL
2830
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
PRIMARY
INN
283
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
PRIMARY
PUBCHEM
3037981
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
PRIMARY
WIKIPEDIA
VIOMYCIN
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
PRIMARY
MESH
D014756
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
PRIMARY
MERCK INDEX
m11253
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
PRIMARY Merck Index
CHEBI
15782
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID0023741
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
PRIMARY
ECHA (EC/EINECS)
251-323-0
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
PRIMARY
CAS
32988-50-4
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
PRIMARY
FDA UNII
YVU35998K5
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
PRIMARY
EVMPD
SUB00078MIG
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
PRIMARY
DRUG BANK
DB06827
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201221
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
PRIMARY
NCI_THESAURUS
C66654
Created by admin on Fri Dec 15 16:15:38 UTC 2023 , Edited by admin on Fri Dec 15 16:15:38 UTC 2023
PRIMARY