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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
Structure of NEOMYCIN B HYDROCHLORIDE

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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Aluminum is a weak agonist for the calcium-sensing receptor.
1999 May
Synthesis and anti-HIV activity of guanidinoglycosides.
2000 Dec 29
A simple classification method for residual antibiotics using E. coli cells transformed by the calcium chloride method and drug resistance plasmid DNA.
2001
Study of aminoglycoside-nucleic acid interactions by an HPLC method.
2001 Apr 23
Split-thickness skin graft donor site dressing: preliminary results of a controlled, clinical comparative study of MEBO and Sofra-Tulle.
2001 Jan
Agenesis of the skull bones.
2001 Jul
Aminoglycoside binding displaces a divalent metal ion in a tRNA-neomycin B complex.
2001 Jun
Are topical antibiotics necessary in the management of otitis externa?
2002 Aug
Stereospecificity of aminoglycoside-ribosomal interactions.
2002 Aug 20
Electron paramagnetic resonance dynamic signatures of TAR RNA-small molecule complexes provide insight into RNA structure and recognition.
2002 Dec 17
Anti-HIV activity of a novel aminoglycoside-arginine conjugate.
2002 Jan
Inhibition of bacterial RNase P by aminoglycoside-arginine conjugates.
2002 Jan 30
[Synthesis of biomimetic analogs of neomycin B].
2002 Jul
Small molecule modulators of HIV Rev/Rev response element interaction identified by random screening.
2002 Jun
Reexamination of neomycin B degradation: efficient preparation of its CD and D rings as protected glycosyl donors.
2002 Oct 3
Mutations in gp41 and gp120 of HIV-1 isolates resistant to hexa-arginine neomycin B conjugate.
2003 Dec 26
Structure-activity relationship of neomycin, paromomycin, and neamine-arginine conjugates, targeting HIV-1 gp120-CXCR4 binding step.
2003 Nov
Insulin induces cobalt uptake in a subpopulation of rat cultured primary sensory neurons.
2003 Nov
A new class of branched aminoglycosides: pseudo-pentasaccharide derivatives of neomycin B.
2003 Oct 2
Aminoglycoside antibiotics reduce glucose reabsorption in kidney through down-regulation of SGLT1.
2003 Sep 5
Efficacy and safety of topical ciprofloxacin/dexamethasone versus neomycin/polymyxin B/hydrocortisone for otitis externa.
2004 Aug
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
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
Introduction of a substituent at the 5"-position of N-Boc neomycin B under Mitsunobu reaction conditions.
2005 Jun 7
Quantitative analysis of shape-specific interactions of Rev response element with a positively charged Rev peptide by capillary electrophoresis.
2005 Nov
Branched aminoglycosides: biochemical studies and antibacterial activity of neomycin B derivatives.
2005 Oct 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
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
Removal of p-xylene with Pseudomonas sp. NBM21 in biofilter.
2006 Oct
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 Fri Dec 15 17:45:14 GMT 2023
Edited
by admin
on Fri Dec 15 17:45:14 GMT 2023
Record UNII
31867650GG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NEOMYCIN B HYDROCHLORIDE
MI  
Common Name English
FRAMYCETIN MONHYDROCHLORIDE
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-, MONOHYDROCHLORIDE
Systematic Name English
NEOMYCIN B HYDROCHLORIDE [MI]
Common Name English
Code System Code Type Description
FDA UNII
31867650GG
Created by admin on Fri Dec 15 17:45:15 GMT 2023 , Edited by admin on Fri Dec 15 17:45:15 GMT 2023
PRIMARY
EPA CompTox
DTXSID70948248
Created by admin on Fri Dec 15 17:45:15 GMT 2023 , Edited by admin on Fri Dec 15 17:45:15 GMT 2023
PRIMARY
MERCK INDEX
m7809
Created by admin on Fri Dec 15 17:45:15 GMT 2023 , Edited by admin on Fri Dec 15 17:45:15 GMT 2023
PRIMARY Merck Index
CAS
25389-99-5
Created by admin on Fri Dec 15 17:45:15 GMT 2023 , Edited by admin on Fri Dec 15 17:45:15 GMT 2023
PRIMARY
PUBCHEM
212925
Created by admin on Fri Dec 15 17:45:15 GMT 2023 , Edited by admin on Fri Dec 15 17:45:15 GMT 2023
PRIMARY
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