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Identification
- Summary
Ribostamycin is a broad spectrum aminoglycoside antibiotic on the list of WHO critical antimicrobials for human medicine.
- Generic Name
- Ribostamycin
- DrugBank Accession Number
- DB03615
- Background
Ribostamycin is an aminoglycoside antibiotic1 isolated from Streptomyces ribosidificus2 listed as one of the World Health Organization's critically important antimicrobials.3
- Type
- Small Molecule
- Groups
- Approved, Experimental
- Structure
Structure for Ribostamycin (DB03615)
- Weight
- Average: 454.4727
Monoisotopic: 454.227493328 - Chemical Formula
- C17H34N4O10
- Synonyms
- Ribostamicina
- Ribostamycin
- Ribostamycin A
- Ribostamycine
- Ribostamycinum
- Vistamycin
- External IDs
- Antibiotic SF 733
- Bu 1709
- SF-733
Pharmacology
- Indication
Not Available
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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
Aminoglycosides work by binding to the bacterial 30S ribosomal subunit (some work by binding to the 50S subunit), inhibiting the translocation of the peptidyl-tRNA from the A-site to the P-site and also causing misreading of mRNA, leaving the bacterium unable to synthesize proteins vital to its growth. However, their exact mechanism of action is not fully known.
Target Actions Organism UProtein disulfide-isomerase Not Available Humans U30S ribosomal protein S12 Not Available Escherichia coli (strain K12) UAminoglycoside N(6')-acetyltransferase type 1 Not Available Salmonella enteritidis UAminoglycoside 2'-N-acetyltransferase Not Available Mycobacterium 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Ribostamycin which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Ribostamycin which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Ribostamycin which could result in a higher serum level. Acenocoumarol The risk or severity of bleeding can be increased when Ribostamycin is combined with Acenocoumarol. Acetaminophen Acetaminophen may decrease the excretion rate of Ribostamycin which could result in a higher serum level. - Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key Ribostamycin sulfate QFN1QU7PEN 53797-35-6 RTCDDYYZMGGHOE-YMSVYGIHSA-N
Categories
- ATC Codes
- J01GB10 — Ribostamycin
- Drug Categories
- Agents that produce neuromuscular block (indirect)
- Aminoglycoside Antibacterials
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Carbohydrates
- Drugs that are Mainly Renally Excreted
- Drugs that are Mainly Renally Excreted with a Narrow Therapeutic Index
- Glycosides
- Narrow Therapeutic Index Drugs
- Nephrotoxic agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 4,5-disubstituted 2-deoxystreptamines. These are 2-deoxystreptamine aminoglycosides that a glycosidically linked to a pyranose of furanose unit at the C4- and C5-positions.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- 4,5-disubstituted 2-deoxystreptamines
- Alternative Parents
- O-glycosyl compounds / Aminocyclitols and derivatives / Cyclohexylamines / Cyclohexanols / Oxanes / Monosaccharides / Tetrahydrofurans / 1,2-aminoalcohols / Oxacyclic compounds / Acetals show 4 more
- Substituents
- 1,2-aminoalcohol / 4,5-disubstituted 2-deoxystreptamine / Acetal / Alcohol / Aliphatic heteromonocyclic compound / Amine / Aminocyclitol or derivatives / Cyclic alcohol / Cyclitol or derivatives / Cyclohexanol show 16 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- aminoglycoside antibiotic, amino cyclitol glycoside (CHEBI:45257)
- Affected organisms
- Humans and other mammals
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 2Q5JOU7T53
- CAS number
- 25546-65-0
- InChI Key
- NSKGQURZWSPSBC-VVPCINPTSA-N
- InChI
- InChI=1S/C17H34N4O10/c18-2-6-10(24)12(26)8(21)16(28-6)30-14-5(20)1-4(19)9(23)15(14)31-17-13(27)11(25)7(3-22)29-17/h4-17,22-27H,1-3,18-21H2/t4-,5+,6-,7-,8-,9+,10-,11-,12-,13-,14-,15-,16-,17+/m1/s1
- IUPAC Name
- (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol
- SMILES
- [H][C@@]1(O[C@@H]2[C@@H](O)[C@H](N)C[C@H](N)[C@H]2O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2N)O[C@H](CO)[C@@H](O)[C@H]1O
References
- Synthesis Reference
Eiichi Akita, Tsutomu Tsuchiya, Shinichi Kondo, Shuntaro Yasuda, Sumio Umezawa, Hamao Umezawa, "1-N-((S)-.alpha.-substituted-.omega.-aminoacyl)-neamine or -ribostamycin and the production thereof." U.S. Patent US4008218, issued February, 1974.
US4008218- General References
- Baud H, Betencourt A, Peyre M, Penasse L: Ribostamycin, as an intermediate in the biosynthesis of neomycin. J Antibiot (Tokyo). 1977 Sep;30(9):720-3. doi: 10.7164/antibiotics.30.720. [Article]
- Zachman-Brockmeyer TR, Thoden JB, Holden HM: The structure of RbmB from Streptomyces ribosidificus, an aminotransferase involved in the biosynthesis of ribostamycin. Protein Sci. 2017 Sep;26(9):1886-1892. doi: 10.1002/pro.3221. Epub 2017 Jul 23. [Article]
- WHO: Critically Important Antimicrobials for Human Medicine 6th Revision [Link]
- External Links
- KEGG Drug
- D08478
- KEGG Compound
- C01759
- PubChem Compound
- 33042
- PubChem Substance
- 46505351
- ChemSpider
- 30581
- ChEBI
- 45257
- ChEMBL
- CHEMBL221572
- ZINC
- ZINC000053255716
- Therapeutic Targets Database
- DNC001211
- PDBe Ligand
- RIO
- Wikipedia
- Ribostamycin
- PDB Entries
- 1m4g / 1s3z / 2bue / 2et5 / 2fcz / 2kxm / 2n0j / 3c3z / 3dvv / 5iqd … show 5 more
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 193.5 °C PhysProp pKa 7.7 MERCK INDEX (1996) - Predicted Properties
Property Value Source Water Solubility 88.7 mg/mL ALOGPS logP -2.9 ALOGPS logP -6.4 Chemaxon logS -0.71 ALOGPS pKa (Strongest Acidic) 12.19 Chemaxon pKa (Strongest Basic) 9.67 Chemaxon Physiological Charge 4 Chemaxon Hydrogen Acceptor Count 14 Chemaxon Hydrogen Donor Count 10 Chemaxon Polar Surface Area 262.38 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 100.17 m3·mol-1 Chemaxon Polarizability 44.9 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8617 Blood Brain Barrier - 0.9659 Caco-2 permeable - 0.7502 P-glycoprotein substrate Non-substrate 0.5164 P-glycoprotein inhibitor I Non-inhibitor 0.8023 P-glycoprotein inhibitor II Non-inhibitor 0.8764 Renal organic cation transporter Non-inhibitor 0.7886 CYP450 2C9 substrate Non-substrate 0.8231 CYP450 2D6 substrate Non-substrate 0.8041 CYP450 3A4 substrate Non-substrate 0.6473 CYP450 1A2 substrate Non-inhibitor 0.9157 CYP450 2C9 inhibitor Non-inhibitor 0.9147 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9034 CYP450 3A4 inhibitor Non-inhibitor 0.9471 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8446 Ames test Non AMES toxic 0.6934 Carcinogenicity Non-carcinogens 0.9505 Biodegradation Not ready biodegradable 0.8587 Rat acute toxicity 1.4850 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9728 hERG inhibition (predictor II) Non-inhibitor 0.81
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0abi-0101900000-26e5b59c86e69d52732d Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0212900000-6a171559948c04cdebd3 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4r-0614900000-4c24a32a02e4ed83cc7b Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0uk9-2409100000-b24a19e0ffc9b3953705 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-03dj-2948100000-82ffd610c05a78a54f2c Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0pi4-2921200000-1b24e0cc169cae3aa437 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 206.8106405 predictedDarkChem Lite v0.1.0 [M-H]- 180.93782 predictedDeepCCS 1.0 (2019) [M+H]+ 206.1946405 predictedDarkChem Lite v0.1.0 [M+H]+ 182.66154 predictedDeepCCS 1.0 (2019) [M+Na]+ 206.4536405 predictedDarkChem Lite v0.1.0 [M+Na]+ 188.85603 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- This multifunctional protein catalyzes the formation, breakage and rearrangement of disulfide bonds. At the cell surface, seems to act as a reductase that cleaves disulfide bonds of proteins attached to the cell. May therefore cause structural modifications of exofacial proteins. Inside the cell, seems to form/rearrange disulfide bonds of nascent proteins. At high concentrations and following phosphorylation by FAM20C, functions as a chaperone that inhibits aggregation of misfolded proteins (PubMed:32149426). At low concentrations, facilitates aggregation (anti-chaperone activity). May be involved with other chaperones in the structural modification of the TG precursor in hormone biogenesis. Also acts as a structural subunit of various enzymes such as prolyl 4-hydroxylase and microsomal triacylglycerol transfer protein MTTP. Receptor for LGALS9; the interaction retains P4HB at the cell surface of Th2 T helper cells, increasing disulfide reductase activity at the plasma membrane, altering the plasma membrane redox state and enhancing cell migration (PubMed:21670307)
- Specific Function
- Actin binding
- Gene Name
- P4HB
- Uniprot ID
- P07237
- Uniprot Name
- Protein disulfide-isomerase
- Molecular Weight
- 57115.795 Da
References
- Horibe T, Nagai H, Sakakibara K, Hagiwara Y, Kikuchi M: Ribostamycin inhibits the chaperone activity of protein disulfide isomerase. Biochem Biophys Res Commun. 2001 Dec 21;289(5):967-72. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Trna binding
- Specific Function
- With S4 and S5 plays an important role in translational accuracy.Interacts with and stabilizes bases of the 16S rRNA that are involved in tRNA selection in the A site and with the mRNA backbone. Lo...
- Gene Name
- rpsL
- Uniprot ID
- P0A7S3
- Uniprot Name
- 30S ribosomal protein S12
- Molecular Weight
- 13736.995 Da
- Kind
- Protein
- Organism
- Salmonella enteritidis
- Pharmacological action
- Unknown
- General Function
- Protein homodimerization activity
- Specific Function
- Catalyzes the transfer of an acetyl group from acetyl-CoA to the 6'-amino group of aminoglycoside molecules conferring resistance to antibiotics containing the purpurosamine ring including amikacin...
- Gene Name
- Not Available
- Uniprot ID
- Q9R381
- Uniprot Name
- Aminoglycoside N(6')-acetyltransferase type 1
- Molecular Weight
- 16361.42 Da
- Kind
- Protein
- Organism
- Mycobacterium tuberculosis
- Pharmacological action
- Unknown
- General Function
- May catalyze the coenzyme A-dependent acetylation of the 2' hydroxyl or amino group of a broad spectrum of aminoglycosides and confer resistance to aminoglycosides (By similarity). In vitro assays show no significant increase of resistance to aminoglycosides, possibly due to low expression in a heterologous system (PubMed:9159528).
- Specific Function
- Aminoglycoside 2'-n-acetyltransferase activity
- Gene Name
- aac
- Uniprot ID
- P9WQG9
- Uniprot Name
- Aminoglycoside 2'-N-acetyltransferase
- Molecular Weight
- 20037.53 Da
Enzymes
- Kind
- Protein
- Organism
- Mycobacterium tuberculosis
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- May catalyze the coenzyme A-dependent acetylation of the 2' hydroxyl or amino group of a broad spectrum of aminoglycosides and confer resistance to aminoglycosides (By similarity). In vitro assays show no significant increase of resistance to aminoglycosides, possibly due to low expression in a heterologous system (PubMed:9159528).
- Specific Function
- Aminoglycoside 2'-n-acetyltransferase activity
- Gene Name
- aac
- Uniprot ID
- P9WQG9
- Uniprot Name
- Aminoglycoside 2'-N-acetyltransferase
- Molecular Weight
- 20037.53 Da
References
- Vong K, Auclair K: Understanding and overcoming aminoglycoside resistance caused by N-6'-acetyltransferase. Medchemcomm. 2012 Apr 1;3(4):397-407. doi: 10.1039/C2MD00253A. [Article]
- Zarate SG, De la Cruz Claure ML, Benito-Arenas R, Revuelta J, Santana AG, Bastida A: Overcoming Aminoglycoside Enzymatic Resistance: Design of Novel Antibiotics and Inhibitors. Molecules. 2018 Jan 30;23(2). pii: molecules23020284. doi: 10.3390/molecules23020284. [Article]
- Shi K, Caldwell SJ, Fong DH, Berghuis AM: Prospects for circumventing aminoglycoside kinase mediated antibiotic resistance. Front Cell Infect Microbiol. 2013 Jun 25;3:22. doi: 10.3389/fcimb.2013.00022. eCollection 2013. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51