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

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]4O[C@H](CN)[C@@H](O)[C@H](O)[C@H]4N)[C@@H]2O)[C@H](N)[C@@H](O)[C@@H]1O

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

Molecular Formula	C23H46N6O13
Molecular Weight	614.6437
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	19 / 19
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 20 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 8504
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 8504

Conditions

Condition	Modality	Highest Phase	Product
Conjunctivitis 17 Sources: http://www.medsafe.govt.nz/profs/Datasheet/s/Soframycineyeeardrop.pdf	Curative	Approved 8583	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 8583	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 8583	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
Determination of neomycin sulfate and impurities using high-performance anion-exchange chromatography with integrated pulsed amperometric detection.	2007-01-04	16860963
Synthesis and antibacterial activity of novel neamine derivatives.	2006-12-15	16997557
Selectively guanidinylated derivatives of neamine. Syntheses and inhibition of anthrax lethal factor protease.	2006-10-01	16870442
Removal of p-xylene with Pseudomonas sp. NBM21 in biofilter.	2006-10	17116573
Rapid analysis of native neomycin components on a portable capillary electrophoresis system with potential gradient detection.	2006-08	16896633
Neonatal deafness results in degraded topographic specificity of auditory nerve projections to the cochlear nucleus in cats.	2006-07-01	16680765
Mixed-type noncompetitive inhibition of anthrax lethal factor protease by aminoglycosides.	2006-07	16817854
Biosolids from two-stage bioleaching could produce compost for unrestricted use.	2006-06	16865922
Prevalence of methicillin-resistant Staphylococcus aureus (MRSA) in community-acquired primary pyoderma.	2006-05-19	16707818
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.	2006-04-15	16413787
Trisaccharide mimetics of the aminoglycoside antibiotic neomycin.	2006-04-07	16557321
The role of phospholipase D and phosphatidic acid in the mechanical activation of mTOR signaling in skeletal muscle.	2006-03-21	16537399
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.	2006-02-01	16178011
Exploring the use of conformationally locked aminoglycosides as a new strategy to overcome bacterial resistance.	2006-01-11	16390137
Mitsunobu dehydration of N-Boc neomycin B.	2006-01-07	16357991
Identification and quantitation of polymyxin B, framycetin, and dexamethasone in an ointment by using thin-layer chromatography with densitometry.	2006-01-03	16386008
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.	2005-12-21	16371160
Neamine inhibits xenografic human tumor growth and angiogenesis in athymic mice.	2005-12-15	16361562
Neamine dimers targeting the HIV-1 TAR RNA.	2005-11-01	16153833
Quantitative analysis of shape-specific interactions of Rev response element with a positively charged Rev peptide by capillary electrophoresis.	2005-11	16240294
Branched aminoglycosides: biochemical studies and antibacterial activity of neomycin B derivatives.	2005-10-15	15993084
Contact allergy to neomycin sulfate: results of a multifactorial analysis.	2005-10	15880442
Analysis of neomycin sulfate and framycetin sulfate by high-performance liquid chromatography using evaporative light scattering detection.	2005-09-16	16130719
Prescription pattern for treatment of hemorrhoids under the universal coverage policy of Thailand.	2005-07	16295562
Disruption and restoration of cell-cell junctions in mouse vestibular epithelia following aminoglycoside treatment.	2005-07	15953529
The RNA-bound conformation of neamine as determined by transferred NOE experiments.	2005-07	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.	2005-06-15	15941249
Introduction of a substituent at the 5"-position of N-Boc neomycin B under Mitsunobu reaction conditions.	2005-06-07	15917888
tRNAPhe cleavage by aminoglycosides is triggered off by formation of an abasic site.	2005-05-27	15845388
Aminoglycosides induce acute cell signaling and chronic cell death in renal cells that express the calcium-sensing receptor.	2005-05	15800129
A blinded in-vitro study to compare the efficacy of five topical ear drops in clearing grommets blocked with thick middle ear effusion fluid.	2005-02	15748186
Binding of manganese(II) to a tertiary stabilized hammerhead ribozyme as studied by electron paramagnetic resonance spectroscopy.	2005-01	15611296
[The effectiveness of some methods in eliminating bacteria from the root canal of a tooth with chronic apical periodontitis].	2005	16519096
The use of perioperative Sofradex eardrops in preventing tympanostomy tube blockage: a prospective double-blinded randomized-controlled trial.	2004-12	15533144
Lipoprotein lipase in hemodialysis patients: indications that low molecular weight heparin depletes functional stores, despite low plasma levels of the enzyme.	2004-11-03	15527497
Molecular evaluation of residual endodontic microorganisms after instrumentation, irrigation and medication with either calcium hydroxide or Septomixine.	2004-11	15533217
Chemoenzymatic synthesis and high-throughput screening of an aminoglycoside-polyamine library: identification of high-affinity displacers and DNA-binding ligands.	2004-10-06	15453764
Delayed neurotrophic treatment preserves nerve survival and electrophysiological responsiveness in neomycin-deafened guinea pigs.	2004-10-01	15372491
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.	2004-10	15521106
A peptide nucleic acid-neamine conjugate that targets and cleaves HIV-1 TAR RNA inhibits viral replication.	2004-09-23	15369382
Disaccharide mimetics of the aminoglycoside antibiotic neamine.	2004-09-06	15368574
Efficacy and safety of topical ciprofloxacin/dexamethasone versus neomycin/polymyxin B/hydrocortisone for otitis externa.	2004-08	15324520
Randomized, double-blind trial comparing topical nitroglycerine with xylocaine and Proctosedyl in idiopathic chronic anal fissure.	2004-07-15	15250565
Ototoxicity after use of neomycin eardrops is unrelated to A1555G point mutation in mitochondrial DNA.	2004-07	15318963
Optimizing the quadruple-potential waveform for the pulsed amperometric detection of neomycin.	2004-06-11	15250400
Inhibition of the proteolytic activity of anthrax lethal factor by aminoglycosides.	2004-04-21	15080670
Interactions of the antibiotics neomycin B and chlortetracycline with the hammerhead ribozyme as studied by Zn2+-dependent RNA cleavage.	2004-03-01	14980615
Changing patterns of contact allergy in chronic inflammatory ear disease.	2004-02	15128318
Integrated, long term, sustainable, cost effective biosolids management at a large Canadian wastewater treatment facility.	2004	15259950
The evaluation of neomycin and other antimicrobial agents of bacterial and fungal origin, and substances from higher plants.	1949-12-14	15398785

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.

Substance Class	Chemical Created by `admin` on `Tue Apr 01 20:44:09 GMT 2025` Edited by `admin` on `Tue Apr 01 20:44:09 GMT 2025`
Record UNII	4BOC774388
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NEOMYCIN B

Preferred Name

English

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 [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