Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C23H46N6O13.3H2O4S |
| Molecular Weight | 908.879 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 19 / 19 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.[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=KWBUARAINLGYMG-JGMIRXPNSA-N
InChI=1S/C23H46N6O13.3H2O4S/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;3*1-5(2,3)4/h5-23,30-36H,1-4,24-29H2;3*(H2,1,2,3,4)/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 |
|
| Aluminum is a weak agonist for the calcium-sensing receptor. | 1999 May |
|
| Synthesis and anti-HIV activity of guanidinoglycosides. | 2000 Dec 29 |
|
| Rescue of hearing, auditory hair cells, and neurons by CEP-1347/KT7515, an inhibitor of c-Jun N-terminal kinase activation. | 2000 Jan 1 |
|
| Temporal bone studies of the human peripheral vestibular system. Aminoglycoside ototoxicity. | 2000 May |
|
| Study of aminoglycoside-nucleic acid interactions by an HPLC method. | 2001 Apr 23 |
|
| Targeted site-specific cleavage of HIV-1 viral Rev responsive element by copper aminoglycosides. | 2001 Feb |
|
| [Optimization of aerosol therapy in otorhinolaryngology: stability and granulometry of dexamethasone-gomenol-framycetin solution]. | 2001 Feb |
|
| Split-thickness skin graft donor site dressing: preliminary results of a controlled, clinical comparative study of MEBO and Sofra-Tulle. | 2001 Jan |
|
| Acute hemorrhagic keratoconjunctivitis after LASIK. | 2001 Mar |
|
| Absorption studies on aminoglycoside binding to the packaging region of human immunodeficiency virus type-1. | 2002 Feb 25 |
|
| Inhibition of bacterial RNase P by aminoglycoside-arginine conjugates. | 2002 Jan 30 |
|
| Inhibition of Klenow DNA polymerase and poly(A)-specific ribonuclease by aminoglycosides. | 2002 Nov |
|
| Inhibition of protein synthesis by aminoglycoside-arginine conjugates. | 2002 Oct |
|
| Are topical antibiotics necessary in the management of otitis externa? | 2003 Aug |
|
| Mutations in gp41 and gp120 of HIV-1 isolates resistant to hexa-arginine neomycin B conjugate. | 2003 Dec 26 |
|
| Aminoglycoside antibiotics reduce glucose reabsorption in kidney through down-regulation of SGLT1. | 2003 Sep 5 |
|
| An approach to enhance specificity against RNA targets using heteroconjugates of aminoglycosides and chloramphenicol (or linezolid). | 2004 Feb 25 |
|
| Optimizing the quadruple-potential waveform for the pulsed amperometric detection of neomycin. | 2004 Jun 11 |
|
| Randomized, double-blind trial comparing topical nitroglycerine with xylocaine and Proctosedyl in idiopathic chronic anal fissure. | 2004 May-Jun |
|
| Delayed neurotrophic treatment preserves nerve survival and electrophysiological responsiveness in neomycin-deafened guinea pigs. | 2004 Oct 1 |
|
| Neamine inhibits xenografic human tumor growth and angiogenesis in athymic mice. | 2005 Dec 15 |
|
| Quantitative analysis of shape-specific interactions of Rev response element with a positively charged Rev peptide by capillary electrophoresis. | 2005 Nov |
|
| Synthesis and antibacterial activity of novel neamine derivatives. | 2006 Dec 15 |
|
| Mitsunobu dehydration of N-Boc neomycin B. | 2006 Jan 7 |
|
| Removal of p-xylene with Pseudomonas sp. NBM21 in biofilter. | 2006 Oct |
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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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C2363
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DBSALT000995
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4146-30-9
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C75943
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Y3720KZ4TQ
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235749
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DTXSID801016143
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100000091050
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223-969-3
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28002-70-2
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SUB02269MIG
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248-770-9
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24978553
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ACTIVE MOIETY
SUBSTANCE RECORD
