NEOMYCIN B HYDROCHLORIDE

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 Search

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

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
Aluminum is a weak agonist for the calcium-sensing receptor.	1999 May	10231437
Rescue of hearing, auditory hair cells, and neurons by CEP-1347/KT7515, an inhibitor of c-Jun N-terminal kinase activation.	2000 Jan 1	10627579
Temporal bone studies of the human peripheral vestibular system. Aminoglycoside ototoxicity.	2000 May	10821231
A simple classification method for residual antibiotics using E. coli cells transformed by the calcium chloride method and drug resistance plasmid DNA.	2001	11327109
Neomycin B-arginine conjugate, a novel HIV-1 Tat antagonist: synthesis and anti-HIV activities.	2001 Dec 25	11747436
Targeted site-specific cleavage of HIV-1 viral Rev responsive element by copper aminoglycosides.	2001 Feb	11293410
[Optimization of aerosol therapy in otorhinolaryngology: stability and granulometry of dexamethasone-gomenol-framycetin solution].	2001 Feb	11240436
Split-thickness skin graft donor site dressing: preliminary results of a controlled, clinical comparative study of MEBO and Sofra-Tulle.	2001 Jan	11192048
Agenesis of the skull bones.	2001 Jul	11527187
Acute hemorrhagic keratoconjunctivitis after LASIK.	2001 Mar	11322141
Are topical antibiotics necessary in the management of otitis externa?	2002 Aug	12169127
Stereospecificity of aminoglycoside-ribosomal interactions.	2002 Aug 20	12173937
Inhibition of bacterial RNase P by aminoglycoside-arginine conjugates.	2002 Jan 30	11821058
Are topical antibiotics necessary in the management of otitis externa?	2003 Aug	12871258
Comparison of compliance between topical aural medications.	2003 Aug	12871247
Effectiveness of ototopical antibiotics for chronic suppurative otitis media in Aboriginal children: a community-based, multicentre, double-blind randomised controlled trial.	2003 Aug 18	12914507
Insulin induces cobalt uptake in a subpopulation of rat cultured primary sensory neurons.	2003 Nov	14622148
Aminoglycoside antibiotics reduce glucose reabsorption in kidney through down-regulation of SGLT1.	2003 Sep 5	12927799
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
An approach to enhance specificity against RNA targets using heteroconjugates of aminoglycosides and chloramphenicol (or linezolid).	2004 Feb 25	14971927
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
Randomized, double-blind trial comparing topical nitroglycerine with xylocaine and Proctosedyl in idiopathic chronic anal fissure.	2004 May-Jun	15250565
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
Chemoenzymatic synthesis and high-throughput screening of an aminoglycoside-polyamine library: identification of high-affinity displacers and DNA-binding ligands.	2004 Oct 6	15453764
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
Prescription pattern for treatment of hemorrhoids under the universal coverage policy of Thailand.	2005 Jul	16295562
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
tRNAPhe cleavage by aminoglycosides is triggered off by formation of an abasic site.	2005 May 27	15845388
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
Synthesis and antibacterial activity of novel neamine derivatives.	2006 Dec 15	16997557
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
The role of phospholipase D and phosphatidic acid in the mechanical activation of mTOR signaling in skeletal muscle.	2006 Mar 21	16537399
Removal of p-xylene with Pseudomonas sp. NBM21 in biofilter.	2006 Oct	17116573
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.

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

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Name

Type

Language

NEOMYCIN B HYDROCHLORIDE

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