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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
Fradiomycin B
Framicetina
Framycetin
Framycétine
Framycetinum
Neomycin B
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Sofra Tulle 10 X 10cmdressing1 %topicalRoussel Canada Inc.1966-12-311996-09-09Canada
Sofra Tulle Strip (10 X 30cm)dressing1 %topicalRoussel Canada Inc.1974-12-311997-08-05Canada
Sofra-tulle Dressing 1%dressing1 %topicalErfa Canada 2012 Inc1994-12-31Not applicableCanada
Sofra-tulle Strip 1%dressing1 %topicalErfa Canada 2012 Inc1995-12-31Not applicableCanada
Soframycin Eye Drops 0.5%drops5 mgophthalmicHoechst Roussel Canada Inc.1995-12-312000-07-28Canada
Soframycin Eye Drops 0.5%drops5 mgophthalmicErfa Canada 2012 Inc2001-08-03Not applicableCanada
Soframycin Eye Drops 5mg/mldrops5 mgophthalmicRoussel Canada Inc.1966-12-311997-08-05Canada
Soframycin Eye Ont 0.5%ointment5 mgophthalmicRoussel Canada Inc.1966-12-311997-08-05Canada
Soframycin Sterile Eye Ointment 0.5%ointment5 mgophthalmicErfa Canada 2012 Inc2001-08-03Not applicableCanada
Soframycin Sterile Eye Ointment 0.5%ointment5 mgophthalmicHoechst Roussel Canada Inc.1995-12-312000-07-28Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
IsofraBouchara
IzofraBouchara
Leukase NDermapharm
PolaRoyal
Sofra-Tullesanofi-aventis
Soframycinsanofi-aventis
SoframycineMelisana
Brand mixtures
NameLabellerIngredients
Sandoz OpticortSandoz Canada Incorporated
Sofracort Ear/eye OintmentRoussel Canada Inc.
Sofracort Sterile Ear/eye DropsSanofi Aventis Canada Inc
Sofracort Sterile Ear/eye OintmentHoechst Roussel Canada Inc.
Soframycin Nasal SprayErfa Canada 2012 Inc
Soframycin OintmentRoussel Canada Inc.
Soframycin Skin OintmentErfa Canada 2012 Inc
Salts
Name/CASStructureProperties
Framycetin sulfate
ThumbNot applicableDBSALT000995
Categories
UNII4BOC774388
CAS number119-04-0
WeightAverage: 614.6437
Monoisotopic: 614.312285588
Chemical FormulaC23H46N6O13
InChI KeyInChIKey=PGBHMTALBVVCIT-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[[email protected]](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](O)[[email protected]](N)C[[email protected]](N)[[email protected]]3O[[email protected]]3O[[email protected]](CN)[C@@H](O)[[email protected]](O)[[email protected]]3N)[C@@H]2O)[[email protected]](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.
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
  • 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 inhibitorNot AvailableNot Available
CYP450 2D6 inhibitorNot AvailableNot Available
CYP450 2C19 inhibitorNot AvailableNot Available
CYP450 3A4 inhibitorNot 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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Solutionophthalmic; otic
Dressingtopical1 %
Ointmentophthalmic; otic
Dropsophthalmic; otic
Dropstopical
Dropsophthalmic5 mg
Spraynasal
Ointmenttopical
Ointmentophthalmic5 mg
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 ReferencesNot 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
Alendronic acidFramycetin may increase the activities of Alendronate.
Amphotericin BAmphotericin B may increase the nephrotoxic activities of Framycetin.
Atracurium besylateFramycetin may increase the activities of Atracurium besylate.
AvibactamAvibactam may increase the nephrotoxic activities of Framycetin.
Botulinum Toxin Type AFramycetin 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 Framycetin.
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Framycetin.
CarboplatinFramycetin may increase the ototoxic activities of Carboplatin.
CefaclorCefaclor may increase the nephrotoxic activities of Framycetin.
CefdinirCefdinir may increase the nephrotoxic activities of Framycetin.
CefiximeCefixime may increase the nephrotoxic activities of Framycetin.
CefotaximeCefotaxime may increase the nephrotoxic activities of Framycetin.
CefotetanCefotetan may increase the nephrotoxic activities of Framycetin.
CefoxitinCefoxitin may increase the nephrotoxic activities of Framycetin.
CefpodoximeCefpodoxime may increase the nephrotoxic activities of Framycetin.
CefprozilCefprozil may increase the nephrotoxic activities of Framycetin.
CeftazidimeCeftazidime may increase the nephrotoxic activities of Framycetin.
CeftibutenCeftibuten may increase the nephrotoxic activities of Framycetin.
CeftriaxoneCeftriaxone may increase the nephrotoxic activities of Framycetin.
CefuroximeCefuroxime may increase the nephrotoxic activities of Framycetin.
CelecoxibCelecoxib may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
Cisatracurium besylateFramycetin may increase the activities of Cisatracurium besylate.
CisplatinCisplatin may increase the nephrotoxic activities of Framycetin.
ClavulanateThe serum concentration of Framycetin can be decreased when it is combined with Clavulanate.
ClodronateFramycetin may increase the activities of Clodronate.
ColistimethateFramycetin may increase the nephrotoxic activities of Colistimethate.
ColistinFramycetin may increase the nephrotoxic activities of Colistin.
CyclosporineFramycetin may increase the nephrotoxic activities of Cyclosporine.
DiclofenacDiclofenac may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
DiflunisalDiflunisal may decrease the excretion rate of Framycetin 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 Framycetin.
Etacrynic acidThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Framycetin.
EtodolacEtodolac may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
FenoprofenFenoprofen may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
FloctafenineFloctafenine may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
FlurbiprofenFlurbiprofen may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
FoscarnetFoscarnet may increase the nephrotoxic activities of Framycetin.
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Framycetin.
IbandronateFramycetin may increase the activities of Ibandronate.
IbuprofenIbuprofen may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
IndomethacinIndomethacin may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
KetoprofenKetoprofen may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
KetorolacKetorolac may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
MannitolMannitol may increase the nephrotoxic activities of Framycetin.
MecamylamineFramycetin may increase the neuromuscular blocking activities of Mecamylamine.
Mefenamic acidMefenamic acid may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
MeloxicamMeloxicam may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
NabumetoneNabumetone may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
NaproxenNaproxen may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
OxaprozinOxaprozin may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
PamidronateFramycetin may increase the activities of Pamidronate.
PancuroniumFramycetin may increase the activities of Pancuronium.
PiperacillinThe serum concentration of Framycetin can be decreased when it is combined with Piperacillin.
PiroxicamPiroxicam may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
RisedronateFramycetin may increase the activities of Risedronate.
RocuroniumFramycetin may increase the activities of Rocuronium.
SuccinylcholineFramycetin may increase the activities of Succinylcholine.
SulindacSulindac may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
TenofovirThe serum concentration of Framycetin can be increased when it is combined with Tenofovir.
Tiaprofenic acidTiaprofenic acid may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
TicarcillinThe serum concentration of Framycetin can be decreased when it is combined with Ticarcillin.
TiludronateFramycetin may increase the activities of Tiludronate.
TolmetinTolmetin may decrease the excretion rate of Framycetin 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 Framycetin.
VancomycinVancomycin may increase the nephrotoxic activities of Framycetin.
VecuroniumFramycetin may increase the activities of Vecuronium.
Zoledronic acidFramycetin may increase the activities of Zoledronate.
Food InteractionsNot Available

Targets

1. 16S rRNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
yes
Actions
inhibitor
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:17139284 ]
  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:17016423 ]
  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:17399988 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
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
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:17139284 ]
  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:17016423 ]
  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:8605174 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
General Function:
Virus receptor activity
Specific Function:
Receptor for the C-X-C chemokine CXCL12/SDF-1 that transduces a signal by increasing intracellular calcium ion levels and enhancing MAPK1/MAPK3 activation. Acts as a receptor for extracellular ubiquitin; leading to enhanced intracellular calcium ions and reduced cellular cAMP levels. Involved in hematopoiesis and in cardiac ventricular septum formation. Also plays an essential role in vasculari...
Gene Name:
CXCR4
Uniprot ID:
P61073
Molecular Weight:
39745.055 Da
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:11747436 ]
  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:14638394 ]
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Drug created on June 13, 2005 07:24 / Updated on January 13, 2014 21:44