Identification

Name
Framycetin
Accession Number
DB00452  (APRD00618)
Type
Small Molecule
Groups
Approved
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 IDs
ANTIBIOTIQUE EF 185
Product Ingredients
IngredientUNIICASInChI Key
Framycetin sulfateY3720KZ4TQ4146-30-9KWBUARAINLGYMG-JGMIRXPNSA-N
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%Solution / drops5 mgOphthalmicErfa Canada 2012 Inc2001-08-03Not applicableCanada
Soframycin Eye Drops 0.5%Solution / drops5 mgOphthalmicHoechst Roussel Canada Inc.1995-12-312000-07-28Canada
Soframycin Eye Drops 5mg/mlSolution / drops5 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 mgOphthalmicHoechst Roussel Canada Inc.1995-12-312000-07-28Canada
Soframycin Sterile Eye Ointment 0.5%Ointment5 mgOphthalmicErfa Canada 2012 Inc2001-08-03Not applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Proctol OintmentFramycetin sulfate (1 %) + Dibucaine hydrochloride (0.5 %) + Esculin (1 %) + Hydrocortisone (0.5 %)OintmentRectalOdan Laboratories Ltd2003-08-06Not applicableCanada
Proctol SuppositoriesFramycetin sulfate (10 mg) + Dibucaine hydrochloride (5 mg) + Esculin (10 mg) + Hydrocortisone (5 mg)SuppositoryRectalOdan Laboratories Ltd2004-03-15Not applicableCanada
Proctosedyl OintmentFramycetin sulfate (10 mg) + Dibucaine hydrochloride (5 mg) + Esculin (10 mg) + Hydrocortisone (5 mg)OintmentRectalHoechst Roussel Canada Inc.1971-12-312006-07-28Canada
Proctosedyl OintmentFramycetin sulfate (1 %) + Dibucaine hydrochloride (0.5 %) + Esculin (1 %) + Hydrocortisone (0.5 %)OintmentRectalAptalis Pharma Canada Ulc2003-04-01Not applicableCanada
Proctosedyl OintmentFramycetin sulfate (10 mg) + Dibucaine hydrochloride (5 mg) + Esculin (10 mg) + Hydrocortisone (5 mg)OintmentRectalRoussel Canada Inc.1959-12-311997-08-05Canada
Proctosedyl SupFramycetin sulfate (10 mg) + Dibucaine hydrochloride (5 mg) + Esculin (10 mg) + Hydrocortisone (5 mg)SuppositoryRectalRoussel Canada Inc.1959-12-311996-09-09Canada
Proctosedyl SuppositoriesFramycetin sulfate (10 mg) + Dibucaine hydrochloride (5 mg) + Esculin (10 mg) + Hydrocortisone (5 mg)SuppositoryRectalHoechst Roussel Canada Inc.1959-12-311999-08-11Canada
Proctosedyl SuppositoriesFramycetin sulfate (10 mg) + Dibucaine hydrochloride (5 mg) + Esculin (10 mg) + Hydrocortisone (5 mg)SuppositoryRectalAptalis Pharma Canada Ulc1997-01-23Not applicableCanada
Sandoz OpticortFramycetin sulfate (5 mg) + Dexamethasone (0.5 mg) + Gramicidin D (0.05 mg)SolutionAuricular (otic); OphthalmicSandoz Canada Incorporated2004-01-16Not applicableCanada
Sandoz Proctomyxin HCFramycetin sulfate (1 %) + Dibucaine hydrochloride (0.5 %) + Esculin (1 %) + Hydrocortisone (0.5 %)OintmentRectalSandoz Canada Incorporated2001-03-09Not applicableCanada
International/Other Brands
Isofra (Bouchara) / Izofra (Bouchara) / Leukase N (Dermapharm) / Pola (Royal) / Sofra-Tulle (sanofi-aventis) / Soframycin (sanofi-aventis) / Soframycine (Melisana)
Categories
UNII
4BOC774388
CAS number
119-04-0
Weight
Average: 614.6437
Monoisotopic: 614.312285588
Chemical Formula
C23H46N6O13
InChI Key
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[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

Pharmacology

Indication

For the treatment of bacterial blepharitis, bacterial bonjunctivitis, corneal injuries, corneal ulcers and meibomianitis. For the prophylaxis of ocular infections following foreign body removal

Associated Conditions
Pharmacodynamics

Framycetin 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 action

Framycetin 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.

TargetActionsOrganism
A16S rRNA
inhibitor
Enteric bacteria and other eubacteria
A30S ribosomal protein S12
inhibitor
Escherichia coli (strain K12)
UC-X-C chemokine receptor type 4
antagonist
Human
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
Toxicity
Not Available
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
PathwayCategory
Neomycin Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(4R)-limonene(4R)-limonene may decrease the excretion rate of Framycetin which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Framycetin which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Framycetin which could result in a higher serum level.
AcetaminophenFramycetin may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be decreased when it is combined with Framycetin.
AcetyldigoxinThe serum concentration of Acetyldigoxin can be decreased when it is combined with Framycetin.
Acetylsalicylic acidThe risk or severity of nephrotoxicity can be increased when Acetylsalicylic acid is combined with Framycetin.
AlclofenacAlclofenac may decrease the excretion rate of Framycetin which could result in a higher serum level.
AlcuroniumFramycetin may increase the respiratory depressant activities of Alcuronium.
Alendronic acidFramycetin may increase the hypocalcemic activities of Alendronic acid.
Food Interactions
Not 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 References
Not Available
External Links
Human Metabolome Database
HMDB0015129
KEGG Compound
C01737
PubChem Compound
8378
PubChem Substance
46508892
ChemSpider
8075
BindingDB
19
ChEBI
7508
ChEMBL
CHEMBL184618
Therapeutic Targets Database
DNC001005
PharmGKB
PA164743181
HET
NMY
Wikipedia
Framycetin
ATC Codes
R01AX08 — FramycetinD09AA01 — FramycetinS01AA07 — Framycetin
AHFS Codes
  • 52:04.04 — Antibacterials
  • 84:04.04 — Antibiotics
PDB Entries
1ei2 / 1i9v / 2a04 / 2b0q / 2et4 / 2fcy / 3c7r / 4lf6 / 4lfb / 4v52
show 7 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Amend
  • Teva Pharmaceutical Industries Ltd.
Dosage forms
FormRouteStrength
OintmentRectal
SuppositoryRectal
SolutionAuricular (otic); Ophthalmic
DressingTopical1 %
Solution / dropsAuricular (otic); Ophthalmic
Solution / dropsTopical
OintmentAuricular (otic); Ophthalmic
Solution / dropsOphthalmic5 mg
OintmentOphthalmic5 mg
SprayNasal
OintmentTopical
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.
Patents
Not Available

Properties

State
Solid
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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 / Disaccharides / Aminocyclitols and derivatives / Cyclohexylamines / Cyclohexanols / Oxanes / Tetrahydrofurans / 1,2-aminoalcohols / Oxacyclic compounds / Acetals
show 4 more
Substituents
4,5-disubstituted 2-deoxystreptamine / Disaccharide / Glycosyl compound / O-glycosyl compound / Aminocyclitol or derivatives / Cyclohexanol / Cyclohexylamine / Cyclitol or derivatives / Oxane / Tetrahydrofuran
show 16 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
aminoglycoside (CHEBI:7508) / 2-Deoxystreptamines (C01737)

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. Lo...
Gene Name
rpsL
Uniprot ID
P0A7S3
Uniprot Name
30S ribosomal protein S12
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 ubiq...
Gene Name
CXCR4
Uniprot ID
P61073
Uniprot Name
C-X-C chemokine receptor type 4
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]

Drug created on June 13, 2005 07:24 / Updated on September 21, 2018 20:42