FRAMYCETIN SULFATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H46N6O13.3H2O4S
Molecular Weight	908.879
Optical Activity	UNSPECIFIED
Defined Stereocenters	19 / 19
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.[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=KWBUARAINLGYMG-JGMIRXPNSA-N

InChI=1S/C23H46N6O13.3H2O4S/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;3*1-5(2,3)4/h5-23,30-36H,1-4,24-29H2;3*(H2,1,2,3,4)/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	H2O4S
Molecular Weight	98.078
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
[Acute renal failure in neomycin-treated pancreatitis patients].	1975 Dec	1227178
[Acute kidney failure in patients with pancreatitis treated with neomycin].	1975 Jun 1	1134796
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
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
Inhibition of the HIV-1 rev-RRE complex formation by unfused aromatic cations.	2001 May	11377168
Outcome of 22 cases of perforated tympanic membrane caused by otomycosis.	2001 Nov	11779301
Stereospecificity of aminoglycoside-ribosomal interactions.	2002 Aug 20	12173937
Electron paramagnetic resonance dynamic signatures of TAR RNA-small molecule complexes provide insight into RNA structure and recognition.	2002 Dec 17	12475232
Displacement of Mn2+ from RNA by K+, Mg2+, neomycin B, and an arginine-rich peptide: indirect detection of nucleic acid/ligand interactions using phosphorus relaxation enhancement.	2002 Dec 18	12475335
Absorption studies on aminoglycoside binding to the packaging region of human immunodeficiency virus type-1.	2002 Feb 25	11844684
Tularemia of the middle ear.	2002 Mar	12005098
Inhibition of Klenow DNA polymerase and poly(A)-specific ribonuclease by aminoglycosides.	2002 Nov	12458793
Delayed hypersensitivity reaction to topical aminoglycosides in patients undergoing middle ear surgery.	2002 Oct	12383298
Are topical antibiotics necessary in the management of otitis externa?	2003 Aug	12871258
Mutations in gp41 and gp120 of HIV-1 isolates resistant to hexa-arginine neomycin B conjugate.	2003 Dec 26	14651977
The Tat antagonist neomycin B hexa-arginine conjugate inhibits gp-120-induced death of human neuroblastoma cells.	2003 Mar	12614324
A new class of branched aminoglycosides: pseudo-pentasaccharide derivatives of neomycin B.	2003 Oct 2	14507176
Aminoglycoside antibiotics reduce glucose reabsorption in kidney through down-regulation of SGLT1.	2003 Sep 5	12927799
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
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
New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method.	2004 Jan	14645324
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
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
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
The RNA-bound conformation of neamine as determined by transferred NOE experiments.	2005 Jul	15937986
Introduction of a substituent at the 5"-position of N-Boc neomycin B under Mitsunobu reaction conditions.	2005 Jun 7	15917888
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
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
Removal of p-xylene with Pseudomonas sp. NBM21 in biofilter.	2006 Oct	17116573

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 16:37:39 GMT 2023` Edited by `admin` on `Fri Dec 15 16:37:39 GMT 2023`
Record UNII	Y3720KZ4TQ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

FRAMYCETIN SULFATE

Common Name

English

NEOMYCIN B, SULFATE (SALT)

Common Name

English

MYACINE

Brand Name

English

NEOMYCIN B SULPHATE

Common Name

English

NEOSULF

Brand Name

English

BIOSOL

Brand Name

English

NEOMYCIN B, SULPHATE (SALT)

Common Name

English

NEOMYCIN B SULFATE

Common Name

English

FRAQUINOL

Brand Name

English

NEOMIX

Brand Name

English

Framycetin sulfate [WHO-DD]

Common Name

English

FRAMYCETIN SULFATE [EP MONOGRAPH]

Common Name

English

NEOBRETTIN

Brand Name

English

NIVEMYCIN

Brand Name

English

SOFRAMYCIN

Brand Name

English

TUTTOMYCIN

Common Name

English

FRAMYCETIN SULFATE [MART.]

Common Name

English

BYKOMYCIN

Brand Name

English

ENDOMIXIN

Brand Name

English

FRAMYCETIN SULPHATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2363