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Identification
NameRibostamycin
Accession NumberDB03615  (EXPT02786)
TypeSmall Molecule
GroupsApproved
Description

A broad-spectrum antimicrobial isolated from Streptomyces ribosifidicus. Ribostamycin, along with other aminoglycosides with the DOS (2-deoxystreptamine) subunit, is an important broad-spectrum antibiotic with important use against human immunodeficiency virus and is considered a critically important antimicrobial by the World Health Organization.

Structure
Thumb
Synonyms
5-Amino-2-Aminomethyl-6-[4,6-Diamino-2-(3,4-Dihydroxy-5-Hydroxymethyl-Tetrahydro-Furan-2-Yloxy)-3-Hydroxy-Cyclohexyloxy]-Tetrahydro-Pyran-3,4-Diol
Ribastamin
RIO
Vistamycin
Xylostacin
Xylostasin
External Identifiers
  • Antibiotic SF 733
  • SF-733
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII2Q5JOU7T53
CAS number25546-65-0
WeightAverage: 454.4727
Monoisotopic: 454.227493328
Chemical FormulaC17H34N4O10
InChI KeyInChIKey=NSKGQURZWSPSBC-NLZFXWNVSA-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-/m0/s1
IUPAC Name
(2S,3R,4S,5S,6R)-5-amino-2-(aminomethyl)-6-{[(1S,2S,3R,4S,6R)-4,6-diamino-2-{[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol
SMILES
NC[C@@H]1O[[email protected]](O[[email protected]]2[[email protected]](N)C[[email protected]](N)[C@@H](O)[C@@H]2O[C@@H]2O[C@@H](CO)[[email protected]](O)[[email protected]]2O)[C@@H](N)[[email protected]](O)[[email protected]]1O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as amino sugars. These are sugars having one alcoholic hydroxy group replaced by an amino group; systematically known as x-amino-x-deoxymonosaccharides. These compounds do not include Glycosylamines.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct ParentAmino sugars
Alternative Parents
Substituents
  • 4,5-disubstituted 2-deoxystreptamine
  • Aminoglycoside core
  • 2-deoxystreptamine aminoglycoside
  • Glucosamine
  • Amino sugar
  • O-glycosyl compound
  • Glycosyl compound
  • Cyclohexylamine
  • Cyclohexanol
  • Oxane
  • Monosaccharide
  • Oxolane
  • Cyclic alcohol
  • Secondary alcohol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionAminoglycosides 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8617
Blood Brain Barrier-0.9659
Caco-2 permeable-0.7502
P-glycoprotein substrateNon-substrate0.5164
P-glycoprotein inhibitor INon-inhibitor0.8023
P-glycoprotein inhibitor IINon-inhibitor0.8764
Renal organic cation transporterNon-inhibitor0.7886
CYP450 2C9 substrateNon-substrate0.8231
CYP450 2D6 substrateNon-substrate0.8041
CYP450 3A4 substrateNon-substrate0.6473
CYP450 1A2 substrateNon-inhibitor0.9157
CYP450 2C9 inhibitorNon-inhibitor0.9147
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9034
CYP450 3A4 inhibitorNon-inhibitor0.9471
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8446
Ames testNon AMES toxic0.6934
CarcinogenicityNon-carcinogens0.9505
BiodegradationNot ready biodegradable0.8587
Rat acute toxicity1.4850 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9728
hERG inhibition (predictor II)Non-inhibitor0.81
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point193.5 °CPhysProp
pKa7.7MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility88.7 mg/mLALOGPS
logP-2.9ALOGPS
logP-6.4ChemAxon
logS-0.71ALOGPS
pKa (Strongest Acidic)12.19ChemAxon
pKa (Strongest Basic)9.93ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area262.38 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity100.17 m3·mol-1ChemAxon
Polarizability44.43 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
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 ReferencesNot Available
External Links
ATC CodesJ01GB10
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
Alendronic acidRibostamycin may increase the activities of Alendronate.
Amphotericin BAmphotericin B may increase the nephrotoxic activities of Ribostamycin.
Atracurium besylateRibostamycin may increase the activities of Atracurium besylate.
AvibactamAvibactam may increase the nephrotoxic activities of Ribostamycin.
Botulinum Toxin Type ARibostamycin may increase the neuromuscular blocking activities of Botulinum Toxin Type A.
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Ribostamycin.
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Ribostamycin.
CarboplatinRibostamycin may increase the ototoxic activities of Carboplatin.
CefaclorCefaclor may increase the nephrotoxic activities of Ribostamycin.
CefdinirCefdinir may increase the nephrotoxic activities of Ribostamycin.
CefiximeCefixime may increase the nephrotoxic activities of Ribostamycin.
CefotaximeCefotaxime may increase the nephrotoxic activities of Ribostamycin.
CefotetanCefotetan may increase the nephrotoxic activities of Ribostamycin.
CefoxitinCefoxitin may increase the nephrotoxic activities of Ribostamycin.
CefpodoximeCefpodoxime may increase the nephrotoxic activities of Ribostamycin.
CefprozilCefprozil may increase the nephrotoxic activities of Ribostamycin.
CeftazidimeCeftazidime may increase the nephrotoxic activities of Ribostamycin.
CeftibutenCeftibuten may increase the nephrotoxic activities of Ribostamycin.
CeftriaxoneCeftriaxone may increase the nephrotoxic activities of Ribostamycin.
CefuroximeCefuroxime may increase the nephrotoxic activities of Ribostamycin.
CelecoxibCelecoxib may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
Cisatracurium besylateRibostamycin may increase the activities of Cisatracurium besylate.
CisplatinCisplatin may increase the nephrotoxic activities of Ribostamycin.
ClavulanateThe serum concentration of Ribostamycin can be decreased when it is combined with Clavulanate.
ClodronateRibostamycin may increase the activities of Clodronate.
ColistimethateRibostamycin may increase the nephrotoxic activities of Colistimethate.
ColistinRibostamycin may increase the nephrotoxic activities of Colistin.
CyclosporineRibostamycin may increase the nephrotoxic activities of Cyclosporine.
DiclofenacDiclofenac may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
DiflunisalDiflunisal may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
DigoxinThe serum concentration of Digoxin can be decreased when it is combined with Ribostamycin.
Etacrynic acidThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Ribostamycin.
EtodolacEtodolac may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
FenoprofenFenoprofen may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
FloctafenineFloctafenine may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
FlurbiprofenFlurbiprofen may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
FoscarnetFoscarnet may increase the nephrotoxic activities of Ribostamycin.
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Ribostamycin.
IbandronateRibostamycin may increase the activities of Ibandronate.
IbuprofenIbuprofen may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
IndomethacinIndomethacin may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
KetoprofenKetoprofen may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
KetorolacKetorolac may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
MannitolMannitol may increase the nephrotoxic activities of Ribostamycin.
MecamylamineRibostamycin may increase the neuromuscular blocking activities of Mecamylamine.
Mefenamic acidMefenamic acid may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
MeloxicamMeloxicam may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
NabumetoneNabumetone may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
NaproxenNaproxen may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
OxaprozinOxaprozin may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
PamidronateRibostamycin may increase the activities of Pamidronate.
PancuroniumRibostamycin may increase the activities of Pancuronium.
PiperacillinThe serum concentration of Ribostamycin can be decreased when it is combined with Piperacillin.
PiroxicamPiroxicam may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
RisedronateRibostamycin may increase the activities of Risedronate.
RocuroniumRibostamycin may increase the activities of Rocuronium.
SuccinylcholineRibostamycin may increase the activities of Succinylcholine.
SulindacSulindac may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
TenofovirThe serum concentration of Ribostamycin can be increased when it is combined with Tenofovir.
Tiaprofenic acidTiaprofenic acid may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
TicarcillinThe serum concentration of Ribostamycin can be decreased when it is combined with Ticarcillin.
TiludronateRibostamycin may increase the activities of Tiludronate.
TolmetinTolmetin may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Ribostamycin.
VancomycinVancomycin may increase the nephrotoxic activities of Ribostamycin.
VecuroniumRibostamycin may increase the activities of Vecuronium.
Zoledronic acidRibostamycin may increase the activities of Zoledronate.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein heterodimerization activity
Specific 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, functions as a...
Gene Name:
P4HB
Uniprot ID:
P07237
Molecular Weight:
57115.795 Da
References
  1. 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. [PubMed:11741285 ]
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. Located at the interface of the 30S and 50S subunits, it traverses the body of the 30S subunit contacting proteins on the other side and probably holding the rRNA structure together. The combined cluste...
Gene Name:
rpsL
Uniprot ID:
P0A7S3
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, tobramycin, dibekacin and ribostamycin. Able to acetylate eukaryotic histone proteins.
Gene Name:
Not Available
Uniprot ID:
Q9R381
Molecular Weight:
16361.42 Da
Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
unknown
General Function:
Involved in N-acetyltransferase activity
Specific Function:
Catalyzes the coenzyme A-dependent acetylation of the 2' hydroxyl or amino group of a broad spectrum of aminoglycosides. It confers resistance to aminoglycosides
Gene Name:
aac
Uniprot ID:
P0A5N0
Molecular Weight:
20038.0 Da

Enzymes

Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
unknown
General Function:
Involved in N-acetyltransferase activity
Specific Function:
Catalyzes the coenzyme A-dependent acetylation of the 2' hydroxyl or amino group of a broad spectrum of aminoglycosides. It confers resistance to aminoglycosides
Gene Name:
aac
Uniprot ID:
P0A5N0
Molecular Weight:
20038.0 Da
Comments
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Drug created on June 13, 2005 07:24 / Updated on December 08, 2015 14:38