You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameFramycetin
Accession NumberDB00452  (APRD00618)
TypeSmall Molecule
GroupsApproved
Description

A component of neomycin that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed)

Structure
Thumb
Synonyms
SynonymLanguageCode
Fradiomycin BNot AvailableNot Available
FramicetinaSpanishINN
FramycetinGermanINN
FramycétineFrenchINN
FramycetinumLatinINN
Neomycin BNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
IsofraBouchara
IzofraBouchara
Leukase NDermapharm
PolaRoyal
Sofra-Tullesanofi-aventis
Soframycinsanofi-aventis
SoframycineMelisana
Brand mixtures
Brand NameIngredients
FrakidexFramycetin and Dexamethasone
FramidexFramycetin and Dexamethasone
Salts
Name/CASStructureProperties
Framycetin sulfate
ThumbNot applicableDBSALT000995
Categories
CAS number119-04-0
WeightAverage: 614.6437
Monoisotopic: 614.312285588
Chemical FormulaC23H46N6O13
InChI KeyPGBHMTALBVVCIT-VCIWKGPPSA-N
InChI
InChI=1S/C23H46N6O13/c24-2-7-13(32)15(34)10(28)21(37-7)40-18-6(27)1-5(26)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(29)16(35)14(33)8(3-25)38-22/h5-23,30-36H,1-4,24-29H2/t5-,6+,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1
IUPAC Name
(2S,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(2R,3S,4R,5S)-5-{[(1R,2R,3S,5R,6S)-3,5-diamino-2-{[(2R,3R,4R,5S,6R)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-hydroxycyclohexyl]oxy}-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}oxane-3,4-diol
SMILES
NC[C@@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](O)[C@H](N)C[C@H](N)[C@H]3O[C@H]3O[C@H](CN)[C@@H](O)[C@H](O)[C@H]3N)[C@@H]2O)[C@H](N)[C@@H](O)[C@@H]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
  • Neamine core
  • Glucosamine
  • Amino sugar
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Cyclohexylamine
  • Cyclohexanol
  • Oxane
  • 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 Descriptors
Pharmacology
IndicationFor the treatment of bacterial blepharitis, bacterial bonjunctivitis, corneal injuries, corneal ulcers and meibomianitis. For the prophylaxis of ocular infections following foreign body removal
PharmacodynamicsFramycetin is used for the treatment of bacterial eye infections such as conjunctivitis. Framycetin is an antibiotic. It is not active against fungi, viruses and most kinds of anaerobic bacteria. Framycetin works by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA, leaving the bacterium unable to synthesize proteins vital to its growth. Framycetin is useful primarily in infections involving aerobic bacteria bacteria.
Mechanism of actionFramycetin binds to specific 30S-subunit proteins and 16S rRNA, four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
PathwayCategorySMPDB ID
Neomycin Action PathwayDrug actionSMP00256
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal AbsorptionNot AvailableNot Available
Blood Brain BarrierNot AvailableNot Available
Caco-2 permeableNot AvailableNot Available
P-glycoprotein substrateNot AvailableNot Available
P-glycoprotein inhibitor INot AvailableNot Available
P-glycoprotein inhibitor IINot AvailableNot Available
Renal organic cation transporterNot AvailableNot Available
CYP450 2C9 substrateNot AvailableNot Available
CYP450 2D6 substrateNot AvailableNot Available
CYP450 3A4 substrateNot AvailableNot Available
CYP450 1A2 substrateNot AvailableNot Available
CYP450 2C9 substrateNot AvailableNot Available
CYP450 2D6 substrateNot AvailableNot Available
CYP450 2C19 substrateNot AvailableNot Available
CYP450 3A4 substrateNot AvailableNot Available
CYP450 inhibitory promiscuityNot AvailableNot Available
Ames testNot AvailableNot Available
CarcinogenicityNot AvailableNot Available
BiodegradationNot AvailableNot Available
Rat acute toxicityNot AvailableNot applicable
hERG inhibition (predictor I)Not AvailableNot Available
hERG inhibition (predictor II)Not AvailableNot Available
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Neomycin Sulfate 500 mg tablet1.39USD tablet
Neomycin 500 mg tablet1.25USD tablet
Neomycin sulfate powder0.84USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP-7.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility64.7 mg/mLALOGPS
logP-2.8ALOGPS
logP-8.4ChemAxon
logS-0.98ALOGPS
pKa (Strongest Acidic)12.29ChemAxon
pKa (Strongest Basic)9.97ChemAxon
Physiological Charge6ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area353.11 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity135.9 m3·mol-1ChemAxon
Polarizability60.87 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Vanangamudi Subramaniam Sulur, Madhavan Srinivasan, Neelakandan Narayanan Chulliel, Haridas Sankar, Kuppusamy Senthilkumar, “Medicinal Cream Made Using Framycetin Sulphate and Chitosan and a Process to Make the Same.” U.S. Patent US20120101056, issued April 26, 2012.

US20120101056
General ReferenceNot Available
External Links
ATC CodesD09AA01R01AX08S01AA07
AHFS Codes
  • 52:04.04
  • 84:04.04
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
Amphotericin BAmphotericin B may enhance the nephrotoxic effect of Aminoglycosides.
AtracuriumMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
Botulinum Toxin Type AMay enhance the neuromuscular-blocking effect of AbobotulinumtoxinA.
Botulinum Toxin Type BMay enhance the neuromuscular-blocking effect of RimabotulinumtoxinB.
BumetanideLoop Diuretics may enhance the adverse/toxic effect of Aminoglycosides. Specifically, nephrotoxicity and ototoxicity.
CapreomycinCapreomycin may enhance the neuromuscular-blocking effect of Aminoglycosides.
CarboplatinMay enhance the ototoxic effect of CARBOplatin. Especially with higher doses of carboplatin.
CefaclorCephalosporins (2nd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefdinirCephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefepimeCephalosporins (4th Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefiximeCephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefotaximeCephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefotetanCephalosporins (2nd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefoxitinCephalosporins (2nd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefpodoximeCephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefprozilCephalosporins (2nd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CeftazidimeCephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CeftibutenCephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CeftriaxoneCephalosporins (3rd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CefuroximeCephalosporins (2nd Generation) may enhance the nephrotoxic effect of Aminoglycosides.
CelecoxibNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
Cisatracurium BesylateMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
CisplatinCISplatin may enhance the nephrotoxic effect of Aminoglycosides.
ClodronateMay enhance the hypocalcemic effect of Bisphosphonate Derivatives.
ColistimethateMay enhance the nephrotoxic effect of Colistimethate. Aminoglycosides may enhance the neuromuscular-blocking effect of Colistimethate.
ColistinMay enhance the nephrotoxic effect of Colistimethate. Aminoglycosides may enhance the neuromuscular-blocking effect of Colistimethate.
DiflunisalNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
DigoxinMay decrease the serum concentration of Cardiac Glycosides. This effect has only been demonstrated with oral aminoglycoside administration. Exceptions: Amikacin; Gentamicin (Systemic); Streptomycin; Tobramycin (Systemic, Oral Inhalation).
Ethacrynic acidLoop Diuretics may enhance the adverse/toxic effect of Aminoglycosides. Specifically, nephrotoxicity and ototoxicity.
EtodolacNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
FenoprofenNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
FloctafenineNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
FoscarnetFoscarnet may enhance the nephrotoxic effect of Aminoglycosides.
FurosemideLoop Diuretics may enhance the adverse/toxic effect of Aminoglycosides. Specifically, nephrotoxicity and ototoxicity.
IbandronateMay enhance the hypocalcemic effect of Bisphosphonate Derivatives.
IbuprofenNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
IndomethacinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
KetoprofenNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
KetorolacNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
MannitolMannitol may enhance the nephrotoxic effect of Aminoglycosides.
Mefenamic acidNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
MeloxicamNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
NabumetoneNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
NaproxenNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
OxaprozinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
PamidronateMay enhance the hypocalcemic effect of Bisphosphonate Derivatives.
PancuroniumMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
PiperacillinPenicillins may decrease the serum concentration of Aminoglycosides. Primarily associated with extended spectrum penicillins, and patients with renal dysfunction.
PiroxicamNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
RisedronateMay enhance the hypocalcemic effect of Bisphosphonate Derivatives.
RocuroniumMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
SuccinylcholineMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
SulindacNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
TenofovirTenofovir may increase the serum concentration of Aminoglycosides. Aminoglycosides may increase the serum concentration of Tenofovir.
Tiaprofenic acidNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
TicarcillinPenicillins may decrease the serum concentration of Aminoglycosides. Primarily associated with extended spectrum penicillins, and patients with renal dysfunction.
TiludronateMay enhance the hypocalcemic effect of Bisphosphonate Derivatives.
TolmetinNonsteroidal Anti-Inflammatory Agents may decrease the excretion of Aminoglycosides. Data only in premature infants.
TorasemideLoop Diuretics may enhance the adverse/toxic effect of Aminoglycosides. Specifically, nephrotoxicity and ototoxicity.
VancomycinVancomycin may enhance the nephrotoxic effect of Aminoglycosides.
VecuroniumMay enhance the respiratory depressant effect of Neuromuscular-Blocking Agents.
ZoledronateMay enhance the hypocalcemic effect of Bisphosphonate Derivatives.
Food InteractionsNot Available

Targets

1. 16S rRNA

Kind: nucleotide

Organism: Enteric bacteria and other eubacteria

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Chao PW, Chow CS: Monitoring aminoglycoside-induced conformational changes in 16S rRNA through acrylamide quenching. Bioorg Med Chem. 2007 Jun 1;15(11):3825-31. Epub 2007 Mar 13. Pubmed

2. 30S ribosomal protein S12

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
30S ribosomal protein S12 P0A7S3 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Famulok M, Huttenhofer A: In vitro selection analysis of neomycin binding RNAs with a mutagenized pool of variants of the 16S rRNA decoding region. Biochemistry. 1996 Apr 9;35(14):4265-70. Pubmed

3. C-X-C chemokine receptor type 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
C-X-C chemokine receptor type 4 P61073 Details

References:

  1. Litovchick A, Lapidot A, Eisenstein M, Kalinkovich A, Borkow G: Neomycin B-arginine conjugate, a novel HIV-1 Tat antagonist: synthesis and anti-HIV activities. Biochemistry. 2001 Dec 25;40(51):15612-23. Pubmed
  2. Borkow G, Vijayabaskar V, Lara HH, Kalinkovich A, Lapidot A: Structure-activity relationship of neomycin, paromomycin, and neamine-arginine conjugates, targeting HIV-1 gp120-CXCR4 binding step. Antiviral Res. 2003 Nov;60(3):181-92. Pubmed

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on January 13, 2014 21:44