Identification

Generic Name
Viomycin
DrugBank Accession Number
DB06827
Background

Viomycin is a tuberactinomycin antibiotic that was used to treat Mycobacterium tuberculosis until it was replaced by the less toxic capreomycin. These drugs bind RNA in bacterial ribosomes and inhibit protein synthesis. Viomycin was derived from the actinomycete Streptomyces puniceus.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 685.69
Monoisotopic: 685.325584661
Chemical Formula
C25H43N13O10
Synonyms
  • Vinacetin A
  • Viomicina
  • Viomycin
  • Viomycine
  • Viomycinum

Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

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. This inhibits protein synthesis.

TargetActionsOrganism
A16S/23S rRNA (cytidine-2'-O)-methyltransferase TlyA
inhibitor
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcenocoumarolThe risk or severity of bleeding can be increased when Viomycin is combined with Acenocoumarol.
AcetophenazineAcetophenazine may increase the neurotoxic activities of Viomycin.
AlimemazineAlimemazine may increase the neurotoxic activities of Viomycin.
AmisulprideAmisulpride may increase the neurotoxic activities of Viomycin.
AmitriptylineAmitriptyline may increase the neurotoxic activities of Viomycin.
AmitriptylinoxideViomycin may increase the neurotoxic activities of Amitriptylinoxide.
AmoxapineAmoxapine may increase the neurotoxic activities of Viomycin.
AripiprazoleAripiprazole may increase the neurotoxic activities of Viomycin.
Aripiprazole lauroxilViomycin may increase the neurotoxic activities of Aripiprazole lauroxil.
AsenapineAsenapine may increase the neurotoxic activities of Viomycin.
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Viomycin sulfateLKO141R05V37883-00-4AQONYROJHRNYQQ-QMAPKBLTSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,4,5,6-tetrahydropyrimidine / Alcohol / Aliphatic heteromonocyclic compound / Alkanolamine / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Azacycle / Beta amino acid or derivatives / Carbonic acid derivative
show 29 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
peptide antibiotic, heterodetic cyclic peptide (CHEBI:15782)
Affected organisms
  • Mycobacterium tuberculosis

Chemical Identifiers

UNII
YVU35998K5
CAS number
32988-50-4
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

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. [Article]
KEGG Compound
C01540
PubChem Compound
3037981
PubChem Substance
175427096
ChemSpider
2301596
ChEBI
15782
ChEMBL
CHEMBL3085436
ZINC
ZINC000049799668
Wikipedia
Viomycin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US7326782No2008-02-052018-08-23US flag

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)8.89ChemAxon
pKa (Strongest Basic)10.42ChemAxon
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

Targets

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Kind
Protein
Organism
Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Acts as a host evasion factor, that significantly contributes to the pathogenesis of M.tuberculosis by modulating adaptive immune responses by inhibiting host-protective Th1 and Th17 cytokine responses as well as autophagy (PubMed:25847237). Catalyzes the 2'-O-methylation at nucleotides C1409 in 16S rRNA and C1920 in 23S rRNA (PubMed:16857584, PubMed:20854656). Is likely involved in ribosomal biogenesis (PubMed:21443791). Also exhibits hemolytic activity in vitro, by binding with and oligomerizing into host cell membranes (PubMed:20854656, PubMed:9611795).
Specific Function
Rna binding
Gene Name
tlyA
Uniprot ID
P9WJ63
Uniprot Name
16S/23S rRNA (cytidine-2'-O)-methyltransferase TlyA
Molecular Weight
28073.885 Da
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. [Article]

Drug created at September 14, 2010 16:21 / Updated at January 02, 2022 11:57