Framycetin

Identification

Summary

Framycetin is an aminoglycoside antibiotic used in various formulations and combinations with other agents to treat hemorrhoids, eye and ear infections, and to reduce nasal carriage of staphylococcus.

Brand Names
Proctol, Proctosedyl, Sofra-tulle, Sofracort, Soframycin
Generic Name
Framycetin
DrugBank Accession Number
DB00452
Background

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

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 614.6437
Monoisotopic: 614.312285588
Chemical Formula
C23H46N6O13
Synonyms
  • Fradiomycin B
  • Framicetina
  • Framycetin
  • Framycétine
  • Framycetinum
  • Neomycin B
External IDs
  • ANTIBIOTIQUE EF 185

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

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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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 ribosomal RNA
inhibitor
Enteric bacteria and other eubacteria
A30S ribosomal protein S12
inhibitor
Escherichia coli (strain K12)
UC-X-C chemokine receptor type 4
antagonist
Humans
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
Medicalerrors
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Toxicity

Not Available

Pathways
PathwayCategory
Neomycin Action PathwayDrug action
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.
DrugInteraction
AbacavirFramycetin may decrease the excretion rate of Abacavir which could result in a higher serum level.
AceclofenacThe risk or severity of nephrotoxicity can be increased when Framycetin is combined with Aceclofenac.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Framycetin is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Framycetin is combined with Acenocoumarol.
AcetaminophenFramycetin may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetylcholineThe therapeutic efficacy of Acetylcholine can be decreased when used in combination with Framycetin.
Acetylsalicylic acidThe risk or severity of nephrotoxicity can be increased when Framycetin is combined with Acetylsalicylic acid.
AclidiniumFramycetin may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineFramycetin may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirThe risk or severity of nephrotoxicity can be increased when Framycetin is combined with Acyclovir.
Interactions
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Food Interactions
No interactions found.

Products

Products
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Product Ingredients
IngredientUNIICASInChI Key
Framycetin sulfateY3720KZ4TQ4146-30-9KWBUARAINLGYMG-JGMIRXPNSA-N
International/Other Brands
Isofra (Bouchara) / Izofra (Bouchara) / Leukase N (Dermapharm) / Pola (Royal) / Sofra-Tulle (sanofi-aventis) / Soframycin (sanofi-aventis) / Soframycine (Melisana)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Sofra Tulle 10 X 10cmDressing1 %TopicalRoussel Canada Inc.1966-12-311996-09-09Canada flag
Sofra Tulle Strip (10 X 30cm)Dressing1 %TopicalRoussel Canada Inc.1974-12-311997-08-05Canada flag
Sofra-tulle Dressing 1%Dressing1 %TopicalErfa Canada 2012 Inc1994-12-31Not applicableCanada flag
Sofra-tulle Strip 1%Dressing1 %TopicalErfa Canada 2012 Inc1995-12-31Not applicableCanada flag
Soframycin Eye Drops 0.5%Solution / drops5 mg / mLOphthalmicErfa Canada 2012 Inc2001-08-03Not applicableCanada flag
Soframycin Eye Drops 0.5%Solution / drops5 mg / mLOphthalmicHoechst Roussel Canada Inc.1995-12-312000-07-28Canada flag
Soframycin Eye Drops 5mg/mlSolution / drops5 mg / mLOphthalmicRoussel Canada Inc.1966-12-311997-08-05Canada flag
Soframycin Eye Ont 0.5%Ointment5 mg / gOphthalmicRoussel Canada Inc.1966-12-311997-08-05Canada flag
Soframycin Sterile Eye Ointment 0.5%Ointment5 mg / gOphthalmicHoechst Roussel Canada Inc.1995-12-312000-07-28Canada flag
Soframycin Sterile Eye Ointment 0.5%Ointment5 mg / gOphthalmicErfa Canada 2012 Inc2001-08-03Not applicableCanada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Odan Proctomyxin HCFramycetin sulfate (1 %) + Cinchocaine hydrochloride (0.5 %) + Esculin (1 %) + Hydrocortisone (0.5 %)OintmentRectalOdan Laboratories Ltd2001-03-09Not applicableCanada flag
Odan Proctomyxin HC SuppositoriesFramycetin sulfate (10 mg) + Cinchocaine hydrochloride (5 mg) + Esculin (10 mg) + Hydrocortisone (5 mg)SuppositoryRectalOdan Laboratories Ltd2001-01-05Not applicableCanada flag
Proctol OintmentFramycetin sulfate (1 %) + Cinchocaine hydrochloride (0.5 %) + Esculin (1 %) + Hydrocortisone (0.5 %)OintmentRectalOdan Laboratories Ltd2003-08-06Not applicableCanada flag
Proctol SuppositoriesFramycetin sulfate (10 mg) + Cinchocaine hydrochloride (5 mg) + Esculin (10 mg) + Hydrocortisone (5 mg)SuppositoryRectalOdan Laboratories Ltd2004-03-15Not applicableCanada flag
ProctosedylFramycetin sulfate (1 %) + Cinchocaine hydrochloride (0.5 %) + Esculin (1 %) + Hydrocortisone (0.5 %)OintmentRectalAptalis Pharma Canada Ulc2003-04-01Not applicableCanada flag
ProctosedylFramycetin sulfate (10 mg) + Cinchocaine hydrochloride (5 mg) + Esculin (10 mg) + Hydrocortisone (5 mg)SuppositoryRectalAptalis Pharma Canada Ulc1997-01-232020-05-27Canada flag
Proctosedyl OintmentFramycetin sulfate (10 mg / g) + Cinchocaine hydrochloride (5 mg / g) + Esculin (10 mg / g) + Hydrocortisone (5 mg / g)OintmentRectalRoussel Canada Inc.1959-12-311997-08-05Canada flag
Proctosedyl OintmentFramycetin sulfate (10 mg / g) + Cinchocaine hydrochloride (5 mg / g) + Esculin (10 mg / g) + Hydrocortisone (5 mg / g)OintmentRectalHoechst Roussel Canada Inc.1971-12-312006-07-28Canada flag
Proctosedyl SupFramycetin sulfate (10 mg) + Cinchocaine hydrochloride (5 mg) + Esculin (10 mg) + Hydrocortisone (5 mg)SuppositoryRectalRoussel Canada Inc.1959-12-311996-09-09Canada flag
Proctosedyl SuppositoriesFramycetin sulfate (10 mg) + Cinchocaine hydrochloride (5 mg) + Esculin (10 mg) + Hydrocortisone (5 mg)SuppositoryRectalHoechst Roussel Canada Inc.1959-12-311999-08-11Canada flag

Categories

ATC Codes
D09AA01 — FramycetinR01AX08 — FramycetinS01AA07 — Framycetin
Drug Categories
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 / Disaccharides / Aminocyclitols and derivatives / Cyclohexylamines / Cyclohexanols / Oxanes / 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 (CHEBI:7508) / 2-Deoxystreptamines (C01737)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
4BOC774388
CAS number
119-04-0
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
(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4S,5R)-4-{[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]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

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
Human Metabolome Database
HMDB0015129
KEGG Drug
D05140
KEGG Compound
C01737
PubChem Compound
8378
PubChem Substance
46508892
ChemSpider
8075
BindingDB
19
RxNav
4556
ChEBI
7508
ChEMBL
CHEMBL184618
ZINC
ZINC000071928291
Therapeutic Targets Database
DNC001005
PharmGKB
PA164743181
PDBe Ligand
NMY
Wikipedia
Neomycin
PDB Entries
1ei2 / 1i9v / 2a04 / 2b0q / 2et4 / 2fcy / 3c7r / 4lf6 / 4lfb / 4v52
show 18 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3RecruitingTreatmentDiffuse Large B-Cell Lymphoma (DLBCL)1
Not AvailableRecruitingNot AvailableDiffuse Large B-Cell Lymphoma (DLBCL)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Amend
  • Teva Pharmaceutical Industries Ltd.
Dosage Forms
FormRouteStrength
OintmentRectal
OintmentRectal; Topical
SuppositoryRectal
SolutionAuricular (otic); Ophthalmic
DressingTopical1 %
DressingTopical
Solution / dropsAuricular (otic); Ophthalmic
Solution / dropsTopical
OintmentAuricular (otic); Ophthalmic
Solution / dropsOphthalmic5 mg / mL
OintmentOphthalmic5 mg / g
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)9.73ChemAxon
Physiological Charge6ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area353.11 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity135.9 m3·mol-1ChemAxon
Polarizability59.47 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

Targets

Drugtargets
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Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
Yes
Actions
Inhibitor
In prokaryotes, the 16S rRNA is essential for recognizing the 5' end of mRNA and hence positioning it correctly on the ribosome. The 16S rRNA has a characteristic secondary structure in which half of the nucleotides are base-paired. The 16S rRNA sequence has been highly conserved and is often used for evolutionary and species comparative analysis.
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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
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. [Article]
  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. [Article]

Drug created on June 13, 2005 13:24 / Updated on July 29, 2021 06:27