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
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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAcute crusting rhinitis•••••••••••••••••
Treatment ofConjunctivitis••••••••••••••••••••••
Treatment ofCorneal abrasion••••••••••••••••••••••
Treatment ofCorneal ulcer••••••••••••••••••••••
Prophylaxis ofInfection•••••••••••••••••
Contraindications & Blackbox Warnings
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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
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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.
Food Interactions
No interactions found.

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-tulleDressing1 %TopicalSearchlight Pharma Inc1995-12-31Not applicableCanada flag
Sofra-tulleDressing1 %TopicalSearchlight Pharma Inc1994-12-31Not applicableCanada flag
Soframycin Eye DropsSolution / drops5 mg / mLOphthalmicSearchlight Pharma 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 Ltd2001-03-092021-08-11Canada flag
Odan Proctomyxin HC SuppositoriesFramycetin sulfate (10 mg) + Cinchocaine hydrochloride (5 mg) + Esculin (10 mg) + Hydrocortisone (5 mg)SuppositoryRectalOdan Laboratories Ltd2001-01-052021-10-07Canada 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 (10 mg) + Cinchocaine hydrochloride (5 mg) + Esculin (10 mg) + Hydrocortisone (5 mg)SuppositoryRectalAptalis Pharma Canada Ulc1997-01-232020-05-27Canada 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
PA450608
PDBe Ligand
NMY
Wikipedia
Neomycin
PDB Entries
1ei2 / 1i9v / 2a04 / 2b0q / 2et4 / 2fcy / 3c7r / 4lf6 / 4lfb / 4v52
show 20 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3RecruitingTreatmentDiffuse Large B-Cell Lymphoma (DLBCL)1
2Not Yet RecruitingTreatmentRecurrent Diffuse Large B-Cell Lymphoma / Refractory Diffuse Large B Cell Lymphoma (DLBCL)1
Not AvailableUnknown StatusNot AvailableDiffuse Large B-Cell Lymphoma (DLBCL)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Amend
  • Teva Pharmaceutical Industries Ltd.
Dosage Forms
FormRouteStrength
OintmentRectal
OintmentRectal; Topical
SolutionAuricular (otic); Ophthalmic
DressingTopical1 %
DressingTopical
Solution / dropsAuricular (otic); Ophthalmic
Solution / dropsTopical
OintmentAuricular (otic); Ophthalmic
Solution / dropsOphthalmic5 mg / mL
SprayNasal
OintmentOphthalmic5 mg / g
SuppositoryRectal
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-MSsplash10-001i-7141290000-1d118bea988327c31f82
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0296-0900113000-e162f76fc79487102eb5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0300229000-64df614cca4440a637d8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0900211000-e3eb78d6cbf8debc304d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1211197000-3c6acb2b495b576818e6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-02t9-4922644000-c7d788f02a2c4d037eb7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0229-1458954000-5e5c33edbb22409921a0
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-241.3378594
predicted
DarkChem Lite v0.1.0
[M-H]-241.3354594
predicted
DarkChem Lite v0.1.0
[M-H]-231.4723594
predicted
DarkChem Lite v0.1.0
[M-H]-235.23814
predicted
DeepCCS 1.0 (2019)
[M+H]+241.2678594
predicted
DarkChem Lite v0.1.0
[M+H]+240.3204594
predicted
DarkChem Lite v0.1.0
[M+H]+230.7331594
predicted
DarkChem Lite v0.1.0
[M+H]+236.99402
predicted
DeepCCS 1.0 (2019)
[M+Na]+241.9307594
predicted
DarkChem Lite v0.1.0
[M+Na]+241.8574594
predicted
DarkChem Lite v0.1.0
[M+Na]+230.1869594
predicted
DarkChem Lite v0.1.0
[M+Na]+243.20485
predicted
DeepCCS 1.0 (2019)

Targets

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Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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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 at June 13, 2005 13:24 / Updated at March 18, 2024 16:48