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Identification
NameFramycetin
Accession NumberDB00452  (APRD00618)
Typesmall molecule
Groupsapproved
Description

A component of neomycin that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed)

Structure
Thumb
Synonyms
SynonymLanguageCode
Fradiomycin BNot AvailableNot Available
FramicetinaSpanishINN
FramycetinGermanINN
Framyc├ętineFrenchINN
FramycetinumLatinINN
Neomycin BNot AvailableNot Available
Salts
Name/CAS Structure Properties
Framycetin sulfate
Thumb Not applicable DBSALT000995
Brand names
NameCompany
IsofraBouchara
IzofraBouchara
Leukase NDermapharm
PolaRoyal
Sofra-Tullesanofi-aventis
Soframycinsanofi-aventis
SoframycineMelisana
Brand mixtures
Brand NameIngredients
FrakidexFramycetin and Dexamethasone
FramidexFramycetin and Dexamethasone
Categories
CAS number119-04-0
WeightAverage: 614.6437
Monoisotopic: 614.312285588
Chemical FormulaC23H46N6O13
InChI KeyInChIKey=PGBHMTALBVVCIT-VCIWKGPPSA-N
InChI
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
IUPAC Name
(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4S,5R)-4-{[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol
SMILES
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]3O[C@H](CN)[C@@H](O)[C@H](O)[C@H]3N)[C@@H]2O)[C@H](N)[C@@H](O)[C@@H]1O
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbohydrates and Carbohydrate Conjugates
SubclassAmino Sugars
Direct parentAminocyclitol Glycosides
Alternative parentsMixed Pentose/Hexose Trisaccharides; O-glycosyl Compounds; Aminocyclitols and Derivatives; Cyclohexanols; Oxanes; Oxolanes; Tetrahydrofurans; 1,2-Diols; 1,2-Aminoalcohols; Polyamines; Primary Alcohols; Acetals; Monoalkylamines
Substituentstrisaccharide; o-glycosyl compound; glycosyl compound; aminocyclitol derivative; cyclitol derivative; cyclohexanol; oxane; oxolane; cyclic alcohol; tetrahydrofuran; secondary alcohol; 1,2-aminoalcohol; 1,2-diol; ether; primary alcohol; acetal; polyamine; alcohol; amine; organonitrogen compound; primary aliphatic amine; primary amine
Classification descriptionThis compound belongs to the aminocyclitol glycosides. These are organic compounds containing an amicocyclitol moiety glycosidially linked to a carbohydrate moiety.
Pharmacology
IndicationFor the treatment of bacterial blepharitis, bacterial bonjunctivitis, corneal injuries, corneal ulcers and meibomianitis. For the prophylaxis of ocular infections following foreign body removal
PharmacodynamicsFramycetin 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.
Mechanism of actionFramycetin 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption Not Available Not Available
Blood Brain Barrier Not Available Not Available
Caco-2 permeable Not Available Not Available
P-glycoprotein substrate Not Available Not Available
P-glycoprotein inhibitor I Not Available Not Available
P-glycoprotein inhibitor II Not Available Not Available
Renal organic cation transporter Not Available Not Available
CYP450 2C9 substrate Not Available Not Available
CYP450 2D6 substrate Not Available Not Available
CYP450 3A4 substrate Not Available Not Available
CYP450 1A2 substrate Not Available Not Available
CYP450 2C9 substrate Not Available Not Available
CYP450 2D6 substrate Not Available Not Available
CYP450 2C19 substrate Not Available Not Available
CYP450 3A4 substrate Not Available Not Available
CYP450 inhibitory promiscuity Not Available Not Available
Ames test Not Available Not Available
Carcinogenicity Not Available Not Available
Biodegradation Not Available Not Available
Rat acute toxicity Not Available Not applicable
hERG inhibition (predictor I) Not Available Not Available
hERG inhibition (predictor II) Not Available Not Available
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
DressingTopical
OintmentOphthalmic
Solution / dropsOphthalmic
Prices
Unit descriptionCostUnit
Neomycin Sulfate 500 mg tablet1.39USDtablet
Neomycin 500 mg tablet1.25USDtablet
Neomycin sulfate powder0.84USDg
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
logP-7.8Not Available
Predicted Properties
PropertyValueSource
water solubility6.47e+01 g/lALOGPS
logP-2.8ALOGPS
logP-8.4ChemAxon
logS-0.98ALOGPS
pKa (strongest acidic)12.29ChemAxon
pKa (strongest basic)9.97ChemAxon
physiological charge6ChemAxon
hydrogen acceptor count19ChemAxon
hydrogen donor count13ChemAxon
polar surface area353.11ChemAxon
rotatable bond count9ChemAxon
refractivity135.9ChemAxon
polarizability60.87ChemAxon
number of rings4ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Vanangamudi Subramaniam Sulur, Madhavan Srinivasan, Neelakandan Narayanan Chulliel, Haridas Sankar, Kuppusamy Senthilkumar, “Medicinal Cream Made Using Framycetin Sulphate and Chitosan and a Process to Make the Same.” U.S. Patent US20120101056, issued April 26, 2012.

US20120101056
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound8378
PubChem Substance46508892
ChemSpider8075
BindingDB19
ChEBI7508
ChEMBLCHEMBL184618
Therapeutic Targets DatabaseDNC001005
PharmGKBPA164743181
Drug Product Database2224887
WikipediaFramycetin
ATC CodesD09AA01R01AX08S01AA07
AHFS Codes
  • 84:04.04
  • 52:04.04
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. 16S rRNA

Kind: nucleotide

Organism: Enteric bacteria and other eubacteria

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Chao PW, Chow CS: Monitoring aminoglycoside-induced conformational changes in 16S rRNA through acrylamide quenching. Bioorg Med Chem. 2007 Jun 1;15(11):3825-31. Epub 2007 Mar 13. Pubmed

2. 30S ribosomal protein S12

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
30S ribosomal protein S12 P0A7S3 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Famulok M, Huttenhofer A: In vitro selection analysis of neomycin binding RNAs with a mutagenized pool of variants of the 16S rRNA decoding region. Biochemistry. 1996 Apr 9;35(14):4265-70. Pubmed

3. C-X-C chemokine receptor type 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
C-X-C chemokine receptor type 4 P61073 Details

References:

  1. Litovchick A, Lapidot A, Eisenstein M, Kalinkovich A, Borkow G: Neomycin B-arginine conjugate, a novel HIV-1 Tat antagonist: synthesis and anti-HIV activities. Biochemistry. 2001 Dec 25;40(51):15612-23. Pubmed
  2. Borkow G, Vijayabaskar V, Lara HH, Kalinkovich A, Lapidot A: Structure-activity relationship of neomycin, paromomycin, and neamine-arginine conjugates, targeting HIV-1 gp120-CXCR4 binding step. Antiviral Res. 2003 Nov;60(3):181-92. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on January 13, 2014 21:44