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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

NCCC[C@H](N)CC(=O)N[C@H]1CNC(=O)[C@@H](NC(=O)\C(NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC1=O)=C\NC(N)=O)[C@H]2C[C@H](O)NC(N)=N2

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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 2
Optical Activity UNSPECIFIED

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.

Originator

Approval Year

1953
193
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
VIOCIN SULFATE

Approved Use

Viomycin is used to fight infections of Mycobacterium tuberculosis.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
50 μg/mL
REVIEW
https://pubmed.ncbi.nlm.nih.gov/6391781/
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/4340029
unhealthy, 58 years
Health Status: unhealthy
Age Group: 58 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/4340029
Other AEs: Hypomagnesemia, Hypocalcemia...
Other AEs:
Hypomagnesemia
Hypocalcemia
Hypokalemia
Sources:
https://pubmed.ncbi.nlm.nih.gov/4340029
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:
https://pubmed.ncbi.nlm.nih.gov/4340029
https://pubmed.ncbi.nlm.nih.gov/13148513
unhealthy
Health Status: unhealthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/4340029
https://pubmed.ncbi.nlm.nih.gov/13148513
Other AEs: Hypocalcemia, Hypokalemia...
Other AEs:
Hypocalcemia
Hypokalemia
Sources:
https://pubmed.ncbi.nlm.nih.gov/4340029
https://pubmed.ncbi.nlm.nih.gov/13148513
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/4340029
unhealthy, 58 years
Health Status: unhealthy
Age Group: 58 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/4340029
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/4340029
unhealthy, 58 years
Health Status: unhealthy
Age Group: 58 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/4340029
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/4340029
unhealthy, 58 years
Health Status: unhealthy
Age Group: 58 years
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/4340029
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:
https://pubmed.ncbi.nlm.nih.gov/4340029
https://pubmed.ncbi.nlm.nih.gov/13148513
unhealthy
Health Status: unhealthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/4340029
https://pubmed.ncbi.nlm.nih.gov/13148513
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:
https://pubmed.ncbi.nlm.nih.gov/4340029
https://pubmed.ncbi.nlm.nih.gov/13148513
unhealthy
Health Status: unhealthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/4340029
https://pubmed.ncbi.nlm.nih.gov/13148513
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:15782
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15782
ZINC
ZINC000049799668
http://zinc15.docking.org/substances/ZINC000049799668
PubMed

PubMed

TitleDatePubMed
Molecular analysis of cross-resistance to capreomycin, kanamycin, amikacin, and viomycin in Mycobacterium tuberculosis.
2005-08
New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method.
2004-01
Developing a dynamic pharmacophore model for HIV-1 integrase.
2000-06-01
Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs.
2000-02-01
Bioluminescence screening in vitro (Bio-Siv) assays for high-volume antimycobacterial drug discovery.
1996-06
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production.
1993-09-24
A Bartter's-like syndrome from capreomycin, and a similar gentamicin tubulopathy.
1986-03
Antibacterial activity of palmitoyltuberactinamine N and di-beta-lysylcapreomycin IIA.
1983-12
In vitro and in vivo susceptibility of atypical mycobacteria to various drugs.
1981-09-01
Chemical studies on tuberactinomycin. 3. The chemical structure of viomycin (tuberactinomycin B).
1972-07
Hypocalcemia, hypomagnesemia and hypokalemia during chemotherapy of pulmonary tuberculosis.
1972-05
[Clinical studies of cochleotoxicosis due to viomycin and kanamycin during tuberculostatic treatment (a prophylactic attempt)].
1968
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.
1967-07
Patents

Patents

JP2002541233A
406
JP2003515526A
470
JP2011510954A
147

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.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:23:18 GMT 2025
Edited
by admin
on Mon Mar 31 18:23:18 GMT 2025
Record UNII
YVU35998K5
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TUBERACTINOMYCIN B
MI  
Preferred Name English
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
Classification Tree Code System Code
NCI_THESAURUS C280
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
Code System Code Type Description
CHEBI
60081
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
PRIMARY
SMS_ID
100000079138
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
PRIMARY
DRUG CENTRAL
2830
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
PRIMARY
INN
283
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
PRIMARY
PUBCHEM
3037981
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
PRIMARY
WIKIPEDIA
VIOMYCIN
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
PRIMARY
MESH
D014756
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
PRIMARY
MERCK INDEX
m11253
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
PRIMARY Merck Index
CHEBI
15782
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
PRIMARY
EPA CompTox
DTXSID0023741
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
PRIMARY
ECHA (EC/EINECS)
251-323-0
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
PRIMARY
CAS
32988-50-4
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
PRIMARY
FDA UNII
YVU35998K5
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
PRIMARY
EVMPD
SUB00078MIG
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
PRIMARY
DRUG BANK
DB06827
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
PRIMARY
ChEMBL
CHEMBL1201221
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
PRIMARY
NCI_THESAURUS
C66654
Created by admin on Mon Mar 31 18:23:18 GMT 2025 , Edited by admin on Mon Mar 31 18:23:18 GMT 2025
PRIMARY
Related Record Type Details
Structure of VIOMYCIN TRIHYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of VIOMYCIN PANTOTHENATE SULFATE
SALT/SOLVATE -> PARENT
Structure of VIOMYCIN SULFATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of VIOMYCIN
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