FRAMYCETIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H46N6O13
Molecular Weight	614.6437
Optical Activity	UNSPECIFIED
Defined Stereocenters	19 / 19
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[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=PGBHMTALBVVCIT-VCIWKGPPSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.drugbank.ca/drugs/DB00452 | http://products.sanofi.ca/en/sofracort.pdf | http://products.sanofi.ca/en/sofracort.pdf

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
30S ribosomal protein S12 19 Target ID: P0A7S3 Gene ID: 24912032\|\|\|947845 Gene Symbol: rpsL Target Organism: Escherichia coli (strain K12) Sources: https://www.drugbank.ca/drugs/DB00452 \| https://www.ncbi.nlm.nih.gov/pubmed/8605174 \| https://www.ncbi.nlm.nih.gov/pubmed/378226	Inhibitor 8297
16S rRNA, bacterial 5 Target ID: 16S rRNA, bacterial Sources: https://www.drugbank.ca/drugs/DB00452 \| https://www.ncbi.nlm.nih.gov/pubmed/8605174 \| https://www.ncbi.nlm.nih.gov/pubmed/17399988	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Conjunctivitis 17 Sources: http://www.medsafe.govt.nz/profs/Datasheet/s/Soframycineyeeardrop.pdf	Curative	Approved 8429	SOFRAMYCIN Approved Use Indications 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.
Otitis externa 20 Sources: http://www.medsafe.govt.nz/profs/Datasheet/s/Soframycineyeeardrop.pdf	Curative	Approved 8429	SOFRAMYCIN Approved Use Indications 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.
Blepharitis 37 Sources: http://www.medsafe.govt.nz/profs/Datasheet/s/Soframycineyeeardrop.pdf	Curative	Approved 8429	SOFRAMYCIN Approved Use Indications 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	15398785
Integrated, long term, sustainable, cost effective biosolids management at a large Canadian wastewater treatment facility.	2004	15259950
Inhibition of the proteolytic activity of anthrax lethal factor by aminoglycosides.	2004 Apr 21	15080670
Efficacy and safety of topical ciprofloxacin/dexamethasone versus neomycin/polymyxin B/hydrocortisone for otitis externa.	2004 Aug	15324520
The use of perioperative Sofradex eardrops in preventing tympanostomy tube blockage: a prospective double-blinded randomized-controlled trial.	2004 Dec	15533144
Changing patterns of contact allergy in chronic inflammatory ear disease.	2004 Feb	15128318
Ototoxicity after use of neomycin eardrops is unrelated to A1555G point mutation in mitochondrial DNA.	2004 Jul	15318963
Optimizing the quadruple-potential waveform for the pulsed amperometric detection of neomycin.	2004 Jun 11	15250400
Interactions of the antibiotics neomycin B and chlortetracycline with the hammerhead ribozyme as studied by Zn2+-dependent RNA cleavage.	2004 Mar 1	14980615
Randomized, double-blind trial comparing topical nitroglycerine with xylocaine and Proctosedyl in idiopathic chronic anal fissure.	2004 May-Jun	15250565
Molecular evaluation of residual endodontic microorganisms after instrumentation, irrigation and medication with either calcium hydroxide or Septomixine.	2004 Nov	15533217
Lipoprotein lipase in hemodialysis patients: indications that low molecular weight heparin depletes functional stores, despite low plasma levels of the enzyme.	2004 Nov 3	15527497
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	15521106
Delayed neurotrophic treatment preserves nerve survival and electrophysiological responsiveness in neomycin-deafened guinea pigs.	2004 Oct 1	15372491
Chemoenzymatic synthesis and high-throughput screening of an aminoglycoside-polyamine library: identification of high-affinity displacers and DNA-binding ligands.	2004 Oct 6	15453764
A peptide nucleic acid-neamine conjugate that targets and cleaves HIV-1 TAR RNA inhibits viral replication.	2004 Sep 23	15369382
Disaccharide mimetics of the aminoglycoside antibiotic neamine.	2004 Sep 6	15368574
[The effectiveness of some methods in eliminating bacteria from the root canal of a tooth with chronic apical periodontitis].	2005	16519096
Neamine inhibits xenografic human tumor growth and angiogenesis in athymic mice.	2005 Dec 15	16361562
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	16371160
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	15748186
Binding of manganese(II) to a tertiary stabilized hammerhead ribozyme as studied by electron paramagnetic resonance spectroscopy.	2005 Jan	15611296
Prescription pattern for treatment of hemorrhoids under the universal coverage policy of Thailand.	2005 Jul	16295562
Disruption and restoration of cell-cell junctions in mouse vestibular epithelia following aminoglycoside treatment.	2005 Jul	15953529
The RNA-bound conformation of neamine as determined by transferred NOE experiments.	2005 Jul	15937986
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	15941249
Introduction of a substituent at the 5"-position of N-Boc neomycin B under Mitsunobu reaction conditions.	2005 Jun 7	15917888
Aminoglycosides induce acute cell signaling and chronic cell death in renal cells that express the calcium-sensing receptor.	2005 May	15800129
tRNAPhe cleavage by aminoglycosides is triggered off by formation of an abasic site.	2005 May 27	15845388
Quantitative analysis of shape-specific interactions of Rev response element with a positively charged Rev peptide by capillary electrophoresis.	2005 Nov	16240294
Neamine dimers targeting the HIV-1 TAR RNA.	2005 Nov 1	16153833
Contact allergy to neomycin sulfate: results of a multifactorial analysis.	2005 Oct	15880442
Branched aminoglycosides: biochemical studies and antibacterial activity of neomycin B derivatives.	2005 Oct 15	15993084
Analysis of neomycin sulfate and framycetin sulfate by high-performance liquid chromatography using evaporative light scattering detection.	2005 Sep 16	16130719
Identification and quantitation of polymyxin B, framycetin, and dexamethasone in an ointment by using thin-layer chromatography with densitometry.	2005 Sep-Oct	16386008
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	16413787
Trisaccharide mimetics of the aminoglycoside antibiotic neomycin.	2006 Apr 7	16557321
Rapid analysis of native neomycin components on a portable capillary electrophoresis system with potential gradient detection.	2006 Aug	16896633
Synthesis and antibacterial activity of novel neamine derivatives.	2006 Dec 15	16997557
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	16178011
Exploring the use of conformationally locked aminoglycosides as a new strategy to overcome bacterial resistance.	2006 Jan 11	16390137
Mitsunobu dehydration of N-Boc neomycin B.	2006 Jan 7	16357991
Mixed-type noncompetitive inhibition of anthrax lethal factor protease by aminoglycosides.	2006 Jul	16817854
Neonatal deafness results in degraded topographic specificity of auditory nerve projections to the cochlear nucleus in cats.	2006 Jul 1	16680765
Biosolids from two-stage bioleaching could produce compost for unrestricted use.	2006 Jun	16865922
The role of phospholipase D and phosphatidic acid in the mechanical activation of mTOR signaling in skeletal muscle.	2006 Mar 21	16537399
Prevalence of methicillin-resistant Staphylococcus aureus (MRSA) in community-acquired primary pyoderma.	2006 Mar-Apr	16707818
Removal of p-xylene with Pseudomonas sp. NBM21 in biofilter.	2006 Oct	17116573
Selectively guanidinylated derivatives of neamine. Syntheses and inhibition of anthrax lethal factor protease.	2006 Oct 1	16870442
Determination of neomycin sulfate and impurities using high-performance anion-exchange chromatography with integrated pulsed amperometric detection.	2007 Jan 4	16860963

Patents

Sample Use Guides

In Vivo Use Guide

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)

In Vitro Use Guide

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.

Name

Type

Language

FRAMYCETIN

Official Name

English

FRAMYGEN

Brand Name

English

FRAMIDAL

Brand Name

English

ACTILIN

Brand Name

English

ANTIBIOTIC PRODUCED BY STREPTOMYCES DECARIS

Common Name

English

NEOMYCIN B

Common Name

English

NEOMYCIN B [MI]

Common Name

English

Framycetin [WHO-DD]

Common Name

English

D-STREPTAMINE, O-2,6-DIAMINO-2,6-DIDEOXY-.BETA.-L-IDOPYRANOSYL-(1->3)-O-.BETA.-D-RIBOFURANOSYL-(1->5)-O-(2,6-DIAMINO-2,6-DIDEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4))-2-DEOXY-

Common Name

English

ANTIBIOTIQUE EF 185

Code

English

framycetin [INN]

Common Name

English

FRADIOMYCIN B

Common Name

English

ENTERFRAM

Brand Name

English

DEKAMYCIN III

Common Name

English

FRANCETIN

Common Name

English

FRAMYCIN

Common Name

English

ANTIBIOTIC 10676

Common Name

English

D-STREPTAMINE, O-2,6-DIAMINO-2,6-DIDEOXY-.ALPHA.-D-GLUCOPYRANOSYL-(1->4)-O-(O-2,6-DIAMINO-2,6-DIDEOXY-.BETA.-L-IDOPYRANOSYL-(1->3)-.BETA.-D-RIBOFURANOSYL-(1->5))-2-DEOXY-

Common Name

English

NEOMYCIN B [USP-RS]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QR01AX08