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.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=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	C23H46N6O13
Molecular Weight	614.6437
Charge	0
Count

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

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

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
The evaluation of neomycin and other antimicrobial agents of bacterial and fungal origin, and substances from higher plants.	1949 Dec 14	15398785
Synthesis and anti-HIV activity of guanidinoglycosides.	2000 Dec 29	11149851
Temporal bone studies of the human peripheral vestibular system. Aminoglycoside ototoxicity.	2000 May	10821231
Neomycin B-arginine conjugate, a novel HIV-1 Tat antagonist: synthesis and anti-HIV activities.	2001 Dec 25	11747436
A hole in the drum. An overview of tympanic membrane perforations.	2002 Aug	12189659
Anti-HIV activity of a novel aminoglycoside-arginine conjugate.	2002 Jan	11684311
Tularemia of the middle ear.	2002 Mar	12005098
Mutations in gp41 and gp120 of HIV-1 isolates resistant to hexa-arginine neomycin B conjugate.	2003 Dec 26	14651977
Effect of neomycin B on rotavirus plus- and minus-strand RNA synthesis.	2003 Jun	12756615
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
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
Delayed neurotrophic treatment preserves nerve survival and electrophysiological responsiveness in neomycin-deafened guinea pigs.	2004 Oct 1	15372491
Chemoenzymatic synthesis and high-throughput screening of an aminoglycoside-polyamine library: identification of high-affinity displacers and DNA-binding ligands.	2004 Oct 6	15453764
Disaccharide mimetics of the aminoglycoside antibiotic neamine.	2004 Sep 6	15368574
Disruption and restoration of cell-cell junctions in mouse vestibular epithelia following aminoglycoside treatment.	2005 Jul	15953529
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
Introduction of a substituent at the 5"-position of N-Boc neomycin B under Mitsunobu reaction conditions.	2005 Jun 7	15917888
Aminoglycosides induce acute cell signaling and chronic cell death in renal cells that express the calcium-sensing receptor.	2005 May	15800129
tRNAPhe cleavage by aminoglycosides is triggered off by formation of an abasic site.	2005 May 27	15845388
Neamine dimers targeting the HIV-1 TAR RNA.	2005 Nov 1	16153833
Contact allergy to neomycin sulfate: results of a multifactorial analysis.	2005 Oct	15880442
Analysis of neomycin sulfate and framycetin sulfate by high-performance liquid chromatography using evaporative light scattering detection.	2005 Sep 16	16130719
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
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
Neonatal deafness results in degraded topographic specificity of auditory nerve projections to the cochlear nucleus in cats.	2006 Jul 1	16680765
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 `Mon Mar 31 18:32:56 GMT 2025` Edited by `admin` on `Mon Mar 31 18:32:56 GMT 2025`
Record UNII	Y3720KZ4TQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BIOSOL

Preferred Name

English

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

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