Explore a selection of our essential drug information below, or:
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
Structure for Viomycin (DB06827)
- 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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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism A16S/23S rRNA (cytidine-2'-O)-methyltransferase TlyA inhibitorMycobacterium 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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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.
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interactions in your softwareAcenocoumarol The risk or severity of bleeding can be increased when Viomycin is combined with Acenocoumarol. Acetophenazine Acetophenazine may increase the neurotoxic activities of Viomycin. Alimemazine Alimemazine may increase the neurotoxic activities of Viomycin. Ambroxol The risk or severity of methemoglobinemia can be increased when Viomycin is combined with Ambroxol. Amisulpride Amisulpride may increase the neurotoxic activities of Viomycin. - Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key Viomycin sulfate LKO141R05V 37883-00-4 AQONYROJHRNYQQ-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
- 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]
- External Links
- KEGG Compound
- C01540
- PubChem Compound
- 3037981
- PubChem Substance
- 175427096
- ChemSpider
- 2301596
- ChEBI
- 15782
- ChEMBL
- CHEMBL3085436
- ZINC
- ZINC000049799668
- Wikipedia
- Viomycin
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US7326782 No 2008-02-05 2018-08-23 US 
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 1.04 mg/mL ALOGPS logP -3.4 ALOGPS logP -11 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) 8.89 Chemaxon pKa (Strongest Basic) 10.42 Chemaxon Physiological Charge 3 Chemaxon Hydrogen Acceptor Count 15 Chemaxon Hydrogen Donor Count 16 Chemaxon Polar Surface Area 390.36 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 171.46 m3·mol-1 Chemaxon Polarizability 66.95 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 258.3182912 predictedDarkChem Lite v0.1.0 [M-H]- 236.20685 predictedDeepCCS 1.0 (2019) [M+H]+ 258.9852912 predictedDarkChem Lite v0.1.0 [M+H]+ 238.10228 predictedDeepCCS 1.0 (2019) [M+Na]+ 258.2212912 predictedDarkChem Lite v0.1.0 [M+Na]+ 244.2375 predictedDeepCCS 1.0 (2019)
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
- 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 May 03, 2024 10:11