Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H46N6O13.ClH |
| Molecular Weight | 651.105 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 19 / 19 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.[H][C@@]3(O[C@@H]1[C@@H](O)[C@H](N)C[C@H](N)[C@@]1([H])O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2N)O[C@H](CO)[C@@H](O[C@@]4([H])O[C@@H](CN)[C@@H](O)[C@H](O)[C@H]4N)[C@H]3O
InChI
InChIKey=ZDPKKZFBEOYUDO-WQDIDPJDSA-N
InChI=1S/C23H46N6O13.ClH/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;1H/t5-,6+,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+;/m1./s1
Framycetin is a component of neomycin that is produced by Streptomyces fradiae. 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. 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. Framycetin is a component of SOFRACORT (Framycetin sulphate - Gramicidin-dexamethasone), indicated for the treatment of blepharitis and infected eczema of the eyelid; allergic, infective and rosacea conjunctivitis;
rosacea keratitis; scleritis and episcleritis; iridocyclitis, and other inflammatory conditions of the
anterior segment of the eye, as well as otitis externa (acute and chronic) and other inflammatory and sebhorrheic conditions of the external ear.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P0A7S3 Gene ID: 24912032|||947845 Gene Symbol: rpsL Target Organism: Escherichia coli (strain K12) |
|||
Target ID: 16S rRNA, bacterial |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | SOFRAMYCIN Approved UseIndications
In the eye: Conjunctivitis, blepharitis, styes, corneal abrasions and burns. Prophylactically
following removal of foreign bodies. Also indicated for corneal ulcers.
In the ear: Otitis externa. |
|||
| Curative | SOFRAMYCIN Approved UseIndications
In the eye: Conjunctivitis, blepharitis, styes, corneal abrasions and burns. Prophylactically
following removal of foreign bodies. Also indicated for corneal ulcers.
In the ear: Otitis externa. |
|||
| Curative | SOFRAMYCIN Approved UseIndications
In the eye: Conjunctivitis, blepharitis, styes, corneal abrasions and burns. Prophylactically
following removal of foreign bodies. Also indicated for corneal ulcers.
In the ear: Otitis externa. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The evaluation of neomycin and other antimicrobial agents of bacterial and fungal origin, and substances from higher plants. | 1949 Dec 14 |
|
| Integrated, long term, sustainable, cost effective biosolids management at a large Canadian wastewater treatment facility. | 2004 |
|
| Inhibition of the proteolytic activity of anthrax lethal factor by aminoglycosides. | 2004 Apr 21 |
|
| Efficacy and safety of topical ciprofloxacin/dexamethasone versus neomycin/polymyxin B/hydrocortisone for otitis externa. | 2004 Aug |
|
| The use of perioperative Sofradex eardrops in preventing tympanostomy tube blockage: a prospective double-blinded randomized-controlled trial. | 2004 Dec |
|
| Changing patterns of contact allergy in chronic inflammatory ear disease. | 2004 Feb |
|
| An approach to enhance specificity against RNA targets using heteroconjugates of aminoglycosides and chloramphenicol (or linezolid). | 2004 Feb 25 |
|
| Ototoxicity after use of neomycin eardrops is unrelated to A1555G point mutation in mitochondrial DNA. | 2004 Jul |
|
| Optimizing the quadruple-potential waveform for the pulsed amperometric detection of neomycin. | 2004 Jun 11 |
|
| Interactions of the antibiotics neomycin B and chlortetracycline with the hammerhead ribozyme as studied by Zn2+-dependent RNA cleavage. | 2004 Mar 1 |
|
| Randomized, double-blind trial comparing topical nitroglycerine with xylocaine and Proctosedyl in idiopathic chronic anal fissure. | 2004 May-Jun |
|
| Molecular evaluation of residual endodontic microorganisms after instrumentation, irrigation and medication with either calcium hydroxide or Septomixine. | 2004 Nov |
|
| Lipoprotein lipase in hemodialysis patients: indications that low molecular weight heparin depletes functional stores, despite low plasma levels of the enzyme. | 2004 Nov 3 |
|
| The efficacies of affected-limb care with penicillin diethylcarbamazine, the combination of both drugs or antibiotic ointment, in the prevention of acute adenolymphangitis during bancroftian filariasis. | 2004 Oct |
|
| Delayed neurotrophic treatment preserves nerve survival and electrophysiological responsiveness in neomycin-deafened guinea pigs. | 2004 Oct 1 |
|
| Chemoenzymatic synthesis and high-throughput screening of an aminoglycoside-polyamine library: identification of high-affinity displacers and DNA-binding ligands. | 2004 Oct 6 |
|
| A peptide nucleic acid-neamine conjugate that targets and cleaves HIV-1 TAR RNA inhibits viral replication. | 2004 Sep 23 |
|
| Disaccharide mimetics of the aminoglycoside antibiotic neamine. | 2004 Sep 6 |
|
| Neamine inhibits xenografic human tumor growth and angiogenesis in athymic mice. | 2005 Dec 15 |
|
| Targeted infection of HIV-1 Env expressing cells by HIV(CD4/CXCR4) vectors reveals a potential new rationale for HIV-1 mediated down-modulation of CD4. | 2005 Dec 21 |
|
| A blinded in-vitro study to compare the efficacy of five topical ear drops in clearing grommets blocked with thick middle ear effusion fluid. | 2005 Feb |
|
| Binding of manganese(II) to a tertiary stabilized hammerhead ribozyme as studied by electron paramagnetic resonance spectroscopy. | 2005 Jan |
|
| Prescription pattern for treatment of hemorrhoids under the universal coverage policy of Thailand. | 2005 Jul |
|
| Disruption and restoration of cell-cell junctions in mouse vestibular epithelia following aminoglycoside treatment. | 2005 Jul |
|
| The RNA-bound conformation of neamine as determined by transferred NOE experiments. | 2005 Jul |
|
| A simple structural-based approach to prevent aminoglycoside inactivation by bacterial defense proteins. Conformational restriction provides effective protection against neomycin-B nucleotidylation by ANT4. | 2005 Jun 15 |
|
| Introduction of a substituent at the 5"-position of N-Boc neomycin B under Mitsunobu reaction conditions. | 2005 Jun 7 |
|
| Aminoglycosides induce acute cell signaling and chronic cell death in renal cells that express the calcium-sensing receptor. | 2005 May |
|
| tRNAPhe cleavage by aminoglycosides is triggered off by formation of an abasic site. | 2005 May 27 |
|
| Quantitative analysis of shape-specific interactions of Rev response element with a positively charged Rev peptide by capillary electrophoresis. | 2005 Nov |
|
| Neamine dimers targeting the HIV-1 TAR RNA. | 2005 Nov 1 |
|
| Contact allergy to neomycin sulfate: results of a multifactorial analysis. | 2005 Oct |
|
| Branched aminoglycosides: biochemical studies and antibacterial activity of neomycin B derivatives. | 2005 Oct 15 |
|
| Analysis of neomycin sulfate and framycetin sulfate by high-performance liquid chromatography using evaporative light scattering detection. | 2005 Sep 16 |
|
| Identification and quantitation of polymyxin B, framycetin, and dexamethasone in an ointment by using thin-layer chromatography with densitometry. | 2005 Sep-Oct |
|
| Neamine derivatives having a nucleobase with a lysine or an arginine as a linker, their synthesis and evaluation as potential inhibitors for HIV TAR-Tat. | 2006 Apr 15 |
|
| Trisaccharide mimetics of the aminoglycoside antibiotic neomycin. | 2006 Apr 7 |
|
| Rapid analysis of native neomycin components on a portable capillary electrophoresis system with potential gradient detection. | 2006 Aug |
|
| Synthesis and antibacterial activity of novel neamine derivatives. | 2006 Dec 15 |
|
| Elucidation of ATP-stimulated stress protein expression of RBA-2 type-2 astrocytes: ATP potentiate HSP60 and Cu/Zn SOD expression and stimulates pI shift of peroxiredoxin II. | 2006 Feb 1 |
|
| Exploring the use of conformationally locked aminoglycosides as a new strategy to overcome bacterial resistance. | 2006 Jan 11 |
|
| Mitsunobu dehydration of N-Boc neomycin B. | 2006 Jan 7 |
|
| Mixed-type noncompetitive inhibition of anthrax lethal factor protease by aminoglycosides. | 2006 Jul |
|
| Neonatal deafness results in degraded topographic specificity of auditory nerve projections to the cochlear nucleus in cats. | 2006 Jul 1 |
|
| Biosolids from two-stage bioleaching could produce compost for unrestricted use. | 2006 Jun |
|
| The role of phospholipase D and phosphatidic acid in the mechanical activation of mTOR signaling in skeletal muscle. | 2006 Mar 21 |
|
| Prevalence of methicillin-resistant Staphylococcus aureus (MRSA) in community-acquired primary pyoderma. | 2006 Mar-Apr |
|
| Removal of p-xylene with Pseudomonas sp. NBM21 in biofilter. | 2006 Oct |
|
| Selectively guanidinylated derivatives of neamine. Syntheses and inhibition of anthrax lethal factor protease. | 2006 Oct 1 |
|
| Determination of neomycin sulfate and impurities using high-performance anion-exchange chromatography with integrated pulsed amperometric detection. | 2007 Jan 4 |
Sample Use Guides
In the eye: 2 drops every one or two hours initially, diminishing to 2 or 3 drops
three times daily.
In the ear: 2 or 3 drops may be instilled into the external auditory meatus thrice
daily; or a wick may be saturated with drops.
Route of Administration:
Otic (auricular)
Of 32 strains of Whitmore 's bacillus, tested by a serial dilution method in tubes, most were inhibited by 25 ug/ml of Framycetin [Soframycin Eoussel]; 4 strains were inhibited by 12.5 ug/ml and 1 strain by 50 ug/ml. The bactericidal concentration was usually 50 ug/ml, with a range from 25-100 ug/ml.
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31867650GG
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DTXSID70948248
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m7809
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25389-99-5
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212925
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ACTIVE MOIETY
SUBSTANCE RECORD
