U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of FRAMYCETIN

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

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

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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.
Curative
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.
Curative
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

PubMed

TitleDatePubMed
The evaluation of neomycin and other antimicrobial agents of bacterial and fungal origin, and substances from higher plants.
1949 Dec 14
Mutations in gp41 and gp120 of HIV-1 isolates resistant to hexa-arginine neomycin B conjugate.
2003 Dec 26
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
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
New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method.
2004 Jan
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
Lipoprotein lipase in hemodialysis patients: indications that low molecular weight heparin depletes functional stores, despite low plasma levels of the enzyme.
2004 Nov 3
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
[The effectiveness of some methods in eliminating bacteria from the root canal of a tooth with chronic apical periodontitis].
2005
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
Patents

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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 13:27:56 GMT 2023
Edited
by admin
on Sat Dec 16 13:27:56 GMT 2023
Record UNII
4BOC774388
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FRAMYCETIN
INN   WHO-DD  
INN  
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
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
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
NCI_THESAURUS C2363
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
WHO-ATC D09AA01
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
WHO-VATC QD09AA01
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
WHO-ATC S01AA07
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
WHO-VATC QJ01GB91
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
WHO-VATC QS01AA07
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
WHO-ATC R01AX08
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
Code System Code Type Description
RXCUI
4556
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C65770
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY
INN
253
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY
DRUG BANK
DB00452
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY
PUBCHEM
8378
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY
DRUG CENTRAL
1896
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY
MESH
D005601
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY
CHEBI
7508
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY
CHEBI
87835
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY
WIKIPEDIA
FRAMYCETIN
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-292-2
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY
SMS_ID
100000091583
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY
ChEMBL
CHEMBL2104426
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY
FDA UNII
4BOC774388
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY
CAS
119-04-0
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY
EVMPD
SUB07814MIG
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY
MERCK INDEX
m7809
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID2023359
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY
RS_ITEM_NUM
1458019
Created by admin on Sat Dec 16 13:27:57 GMT 2023 , Edited by admin on Sat Dec 16 13:27:57 GMT 2023
PRIMARY
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