Viomycin

Identification

Name
Viomycin
Accession Number
DB06827
Type
Small Molecule
Groups
Approved
Description

Viomycin is a member of the tuberactinomycin family, a group of nonribosomal peptide antibiotics exhibiting anti-tuberculosis properties. 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 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 biosynthesis. It is produced by the actinomycete Streptomyces puniceus, that binds to RNA and inhibits prokaryotic protein synthesis and certain forms of RNA splicing. [Wikipedia]

Structure
Thumb
Synonyms
  • viomicina
Product Ingredients
IngredientUNIICASInChI Key
Viomycin sulfateLKO141R05V37883-00-4AQONYROJHRNYQQ-QMAPKBLTSA-N
Categories
UNII
YVU35998K5
CAS number
32988-50-4
Weight
Average: 685.69
Monoisotopic: 685.325584661
Chemical Formula
C25H43N13O10
InChI Key
GXFAIFRPOKBQRV-GHXCTMGLSA-N
InChI
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
IUPAC Name
(3S)-3,6-diamino-N-[(3S,6Z,9S,12S,15S)-6-[(carbamoylamino)methylidene]-3-[(4R,6S)-6-hydroxy-2-imino-1,3-diazinan-4-yl]-9,12-bis(hydroxymethyl)-2,5,8,11,14-pentaoxo-1,4,7,10,13-pentaazacyclohexadecan-15-yl]hexanamide
SMILES
[H][C@@]1(C[C@H](O)NC(=N)N1)[C@]1([H])NC(=O)\C(NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CNC1=O)NC(=O)C[C@@H](N)CCCN)=C\NC(N)=O

Pharmacology

Indication

Viomycin is an essential component in the drug cocktail currently used to fight infections of Mycobacterium tuberculosis.

Pharmacodynamics
Not Available
Mechanism of action

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.

TargetActionsOrganism
A70S ribosomeNot AvailableMycobacterium tuberculosis
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Mycobacterium tuberculosis
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Viomycin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Viomycin is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Viomycin is combined with 4-hydroxycoumarin.
AcenocoumarolThe risk or severity of bleeding can be increased when Viomycin is combined with Acenocoumarol.
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Viomycin.
Anthrax immune globulin humanThe therapeutic efficacy of Anthrax immune globulin human can be decreased when used in combination with Viomycin.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Viomycin.
Bacillus calmette-guerin substrain connaught live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Viomycin.
Bacillus calmette-guerin substrain danish 1331 live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain danish 1331 live antigen can be decreased when used in combination with Viomycin.
Bacillus calmette-guerin substrain tice live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Viomycin.
Food Interactions
Not Available

References

Synthesis Reference

Michael G. Thomas, Yolanda A. Chan, Sarah G. Ozanick, "Metabolic engineering of viomycin biosynthesis." U.S. Patent US7326782, issued February 5, 2008.

General References
  1. Noda T, Take T, Nagata A, Wakamiya T, Shiba T: Chemical studies on tuberactinomycin. 3. The chemical structure of viomycin (tuberactinomycin B). J Antibiot (Tokyo). 1972 Jul;25(7):427-8. [PubMed:4350196]
External Links
KEGG Compound
C01540
PubChem Compound
3037981
PubChem Substance
175427096
ChEBI
15782
ChEMBL
CHEMBL3085436
Wikipedia
Viomycin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7326782No2008-02-052018-08-23Us

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.04 mg/mLALOGPS
logP-3.4ALOGPS
logP-11ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)10.5ChemAxon
pKa (Strongest Basic)10.14ChemAxon
Physiological Charge3ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area390.36 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity171.46 m3·mol-1ChemAxon
Polarizability66.95 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Peptidomimetics
Sub Class
Hybrid peptides
Direct Parent
Hybrid peptides
Alternative Parents
N-acyl-alpha amino acids and derivatives / Macrolactams / Beta amino acids and derivatives / N-acyl amines / Hydropyrimidines / Vinylogous amides / Ureas / Secondary carboxylic acid amides / Lactams / Guanidines
show 10 more
Substituents
Hybrid peptide / N-acyl-alpha amino acid or derivatives / Macrolactam / Beta amino acid or derivatives / Alpha-amino acid or derivatives / N-acyl-amine / Fatty amide / Fatty acyl / 1,4,5,6-tetrahydropyrimidine / Hydropyrimidine
show 29 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
peptide antibiotic, heterodetic cyclic peptide (CHEBI:15782)

Targets

1. 70S ribosome
Kind
Protein group
Organism
Mycobacterium tuberculosis
Pharmacological action
Yes
References
  1. Stanley RE, Blaha G, Grodzicki RL, Strickler MD, Steitz TA: The structures of the anti-tuberculosis antibiotics viomycin and capreomycin bound to the 70S ribosome. Nat Struct Mol Biol. 2010 Mar;17(3):289-93. doi: 10.1038/nsmb.1755. Epub 2010 Feb 14. [PubMed:20154709]

Drug created on September 14, 2010 10:21 / Updated on November 02, 2018 08:44