U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C25H43N13O10.H2O4S
Molecular Weight 783.768
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of VIOMYCIN SULFATE

SMILES

OS(O)(=O)=O.[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=AQONYROJHRNYQQ-QMAPKBLTSA-N
InChI=1S/C25H43N13O10.H2O4S/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;1-5(2,3)4/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);(H2,1,2,3,4)/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.

Originator

Approval Year

1953
193
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
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
Co-administed with::
pyrazinamide
Sources:
https://pubmed.ncbi.nlm.nih.gov/4340029
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: tubersulosis
Age Group: 58 years
Sex: M
Population Size: 1
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
Condition: tubersulosis
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
Co-administed with::
pyrazinamide
Sources:
https://pubmed.ncbi.nlm.nih.gov/4340029
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: tubersulosis
Age Group: 58 years
Sex: M
Population Size: 1
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
Co-administed with::
pyrazinamide
Sources:
https://pubmed.ncbi.nlm.nih.gov/4340029
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: tubersulosis
Age Group: 58 years
Sex: M
Population Size: 1
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
Co-administed with::
pyrazinamide
Sources:
https://pubmed.ncbi.nlm.nih.gov/4340029
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: tubersulosis
Age Group: 58 years
Sex: M
Population Size: 1
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
Condition: tubersulosis
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
Condition: tubersulosis
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
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
[Clinical studies of cochleotoxicosis due to viomycin and kanamycin during tuberculostatic treatment (a prophylactic attempt)].
1968
Chemical studies on tuberactinomycin. 3. The chemical structure of viomycin (tuberactinomycin B).
1972 Jul
Hypocalcemia, hypomagnesemia and hypokalemia during chemotherapy of pulmonary tuberculosis.
1972 May
In vitro and in vivo susceptibility of atypical mycobacteria to various drugs.
1981 Sep-Oct
Antibacterial activity of palmitoyltuberactinamine N and di-beta-lysylcapreomycin IIA.
1983 Dec
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
New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method.
2004 Jan
Molecular analysis of cross-resistance to capreomycin, kanamycin, amikacin, and viomycin in Mycobacterium tuberculosis.
2005 Aug
Patents

Patents

JP2002541233A
400
JP2003515526A
462
JP2011510954A
143

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 SULFATE
JAN   MART.   MI   ORANGE BOOK   USP-RS   WHO-DD  
Common Name English
VIOMYCIN SULFATE [JAN]
Common Name English
VIOMYCIN SULFATE [ORANGE BOOK]
Common Name English
VIOMYCIN SULFATE [MI]
Common Name English
VIOMYCIN SULFATE [MART.]
Common Name English
NSC-760360
Code English
VIOMYCIN SULPHATE
Common Name English
FLORIMYCIN SULFATE
Common Name English
VIOCIN SULFATE
Brand Name English
VIOMYCIN SULFATE [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C280
Created by admin on Fri Dec 15 14:57:42 GMT 2023 , Edited by admin on Fri Dec 15 14:57:42 GMT 2023
Code System Code Type Description
FDA UNII
LKO141R05V
Created by admin on Fri Dec 15 14:57:42 GMT 2023 , Edited by admin on Fri Dec 15 14:57:42 GMT 2023
PRIMARY
CAS
39750-30-6
Created by admin on Fri Dec 15 14:57:42 GMT 2023 , Edited by admin on Fri Dec 15 14:57:42 GMT 2023
ALTERNATIVE
MERCK INDEX
m11467
Created by admin on Fri Dec 15 14:57:42 GMT 2023 , Edited by admin on Fri Dec 15 14:57:42 GMT 2023
PRIMARY Merck Index
EVMPD
SUB05106MIG
Created by admin on Fri Dec 15 14:57:42 GMT 2023 , Edited by admin on Fri Dec 15 14:57:42 GMT 2023
PRIMARY
ChEMBL
CHEMBL1201221
Created by admin on Fri Dec 15 14:57:42 GMT 2023 , Edited by admin on Fri Dec 15 14:57:42 GMT 2023
PRIMARY
DRUG BANK
DBSALT000952
Created by admin on Fri Dec 15 14:57:42 GMT 2023 , Edited by admin on Fri Dec 15 14:57:42 GMT 2023
PRIMARY
SMS_ID
100000087901
Created by admin on Fri Dec 15 14:57:42 GMT 2023 , Edited by admin on Fri Dec 15 14:57:42 GMT 2023
PRIMARY
PUBCHEM
5282488
Created by admin on Fri Dec 15 14:57:42 GMT 2023 , Edited by admin on Fri Dec 15 14:57:42 GMT 2023
PRIMARY
CAS
37883-00-4
Created by admin on Fri Dec 15 14:57:42 GMT 2023 , Edited by admin on Fri Dec 15 14:57:42 GMT 2023
PRIMARY
NCI_THESAURUS
C66655
Created by admin on Fri Dec 15 14:57:42 GMT 2023 , Edited by admin on Fri Dec 15 14:57:42 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of VIOMYCIN
SUBSTANCE RECORD
Structure of VIOMYCIN SULFATE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966