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Identification
NameKanamycin
Accession NumberDB01172  (APRD00026)
TypeSmall Molecule
GroupsApproved, Vet Approved
Description

Kanamycin (also known as kanamycin A) is an aminoglycoside bacteriocidal antibiotic, available in oral, intravenous, and intramuscular forms, and used to treat a wide variety of infections. Kanamycin is isolated from the bacterium Streptomyces kanamyceticus and its most commonly used form is kanamycin sulfate.

Structure
Thumb
Synonyms
4,6-diamino-2-hydroxy-1,3-cyclohexane 3,6'diamino-3,6'-dideoxydi-α-D-glucoside
4,6-diamino-2-hydroxy-1,3-cyclohexylene 3,6'-diamino-3,6'-dideoxydi-D-glucopyranoside
Kanamycin A
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EfficinLupin
KanamytrexAlcon
KancinAlembic
Kancin-LAtlantic
KantrexMerck
WinamycinWinston
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Kanamycin sulfate
Thumb
  • InChI Key: OOYGSFOGFJDDHP-KMCOLRRFSA-N
  • Monoisotopic Mass: 582.205437256
  • Average Mass: 582.577
DBSALT000401
Categories
UNIIRUC37XUP2P
CAS number8063-07-8
WeightAverage: 484.4986
Monoisotopic: 484.238058014
Chemical FormulaC18H36N4O11
InChI KeyInChIKey=SBUJHOSQTJFQJX-LCMAVPODNA-N
InChI
InChI=1/C18H36N4O11/c19-2-6-10(25)12(27)13(28)18(30-6)33-16-5(21)1-4(20)15(14(16)29)32-17-11(26)8(22)9(24)7(3-23)31-17/h4-18,23-29H,1-3,19-22H2/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-/s2
IUPAC Name
(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-3-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}oxane-3,4,5-triol
SMILES
NC[[email protected]]1O[[email protected]](O[C@@H]2[C@@H](N)C[C@@H](N)[[email protected]](O[[email protected]]3O[[email protected]](CO)[C@@H](O)[[email protected]](N)[[email protected]]3O)[[email protected]]2O)[[email protected]](O)[C@@H](O)[C@@H]1O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as amino sugars. These are sugars having one alcoholic hydroxy group replaced by an amino group; systematically known as x-amino-x-deoxymonosaccharides. These compounds do not include Glycosylamines.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassAminosaccharides
Direct ParentAmino sugars
Alternative Parents
Substituents
  • 4,6-disubstituted 2-deoxystreptamine
  • Aminoglycoside core
  • 2-deoxystreptamine aminoglycoside
  • Glucosamine
  • Amino sugar
  • O-glycosyl compound
  • Glycosyl compound
  • Cyclohexylamine
  • Cyclohexanol
  • Oxane
  • Monosaccharide
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationFor treatment of infections where one or more of the following are the known or suspected pathogens: E. coli, Proteus species (both indole-positive and indole-negative), E. aerogenes, K. pneumoniae, S. marcescens, and Acinetobacter species.
PharmacodynamicsKanamycin is an aminoglycoside antibiotic. Aminoglycosides work by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA, leaving the bacterium unable to synthesize proteins vital to its growth. Aminoglycosides are useful primarily in infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. In addition, some mycobacteria, including the bacteria that cause tuberculosis, are susceptible to aminoglycosides. Infections caused by Gram-positive bacteria can also be treated with aminoglycosides, but other types of antibiotics are more potent and less damaging to the host. In the past the aminoglycosides have been used in conjunction with penicillin-related antibiotics in streptococcal infections for their synergistic effects, particularly in endocarditis. Aminoglycosides are mostly ineffective against anaerobic bacteria, fungi and viruses.
Mechanism of actionAminoglycosides like kanamycin "irreversibly" bind to specific 30S-subunit proteins and 16S rRNA. Specifically Kanamycin binds to 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.
Related Articles
AbsorptionKanamycin is rapidly absorbed after intramuscular injection and peak serum levels are generally reached within approximately one hour. Poor oral and topical absorption except with severe skin damage.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half life2.5 hours
ClearanceNot Available
ToxicityMild and reversible nephrotoxicity may be observed in 5 - 25% of patients. Amikacin accumulates in proximal renal tubular cells. Tubular cell regeneration occurs despite continued drug exposure. Toxicity usually occurs several days following initiation of therapy. May cause irreversible ototoxicity. Otoxocity appears to be correlated to cumulative lifetime exposure. Drug accumulation in the endolymph and perilymph of the inner ear causes irreversible damage to hair cells of the cochlea or summit of ampullar cristae in the vestibular complex. High frequency hearing is lost first with progression leading to loss of low frequency hearing. Further toxicity may lead to retrograde degeneration of the 8th cranial (vestibulocochlear) nerve. Vestibular toxicity may cause vertigo, nausea, vomiting, dizziness and loss of balance. Oral LD50 is 17500 mg/kg in mice, over 4 g/kg in rats, and over 3 g/kg in rabbits.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
PathwayCategorySMPDB ID
Kanamycin Action PathwayDrug actionSMP00255
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9351
Blood Brain Barrier-0.9815
Caco-2 permeable-0.7545
P-glycoprotein substrateSubstrate0.5281
P-glycoprotein inhibitor INon-inhibitor0.7592
P-glycoprotein inhibitor IINon-inhibitor0.904
Renal organic cation transporterNon-inhibitor0.8353
CYP450 2C9 substrateNon-substrate0.8325
CYP450 2D6 substrateNon-substrate0.8323
CYP450 3A4 substrateNon-substrate0.6719
CYP450 1A2 substrateNon-inhibitor0.9143
CYP450 2C9 inhibitorNon-inhibitor0.9259
CYP450 2D6 inhibitorNon-inhibitor0.9317
CYP450 2C19 inhibitorNon-inhibitor0.915
CYP450 3A4 inhibitorNon-inhibitor0.97
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9261
Ames testNon AMES toxic0.7406
CarcinogenicityNon-carcinogens0.9488
BiodegradationNot ready biodegradable0.849
Rat acute toxicity1.5431 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9772
hERG inhibition (predictor II)Non-inhibitor0.8151
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Kanamycin sulfate powder25.2USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP-6.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility92.3 mg/mLALOGPS
logP-3.1ALOGPS
logP-7.1ChemAxon
logS-0.72ALOGPS
pKa (Strongest Acidic)12.11ChemAxon
pKa (Strongest Basic)9.75ChemAxon
Physiological Charge4ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area282.61 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity106.13 m3·mol-1ChemAxon
Polarizability47.57 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Hamao Umezawa, Shinichi Kondo, “Method for production of kanamycin C and its derivatives.” U.S. Patent US4120955, issued December, 1975.

US4120955
General ReferencesNot Available
External Links
ATC CodesA07AA08J01GB04S01AA24
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (71.9 KB)
Interactions
Drug Interactions
Drug
Alendronic acidKanamycin may increase the activities of Alendronate.
AmdinocillinThe serum concentration of Kanamycin can be decreased when it is combined with Amdinocillin.
AmoxicillinThe serum concentration of Kanamycin can be decreased when it is combined with Amoxicillin.
Amphotericin BAmphotericin B may increase the nephrotoxic activities of Kanamycin.
AmpicillinThe serum concentration of Kanamycin can be decreased when it is combined with Ampicillin.
Atracurium besylateKanamycin may increase the activities of Atracurium besylate.
AvibactamAvibactam may increase the nephrotoxic activities of Kanamycin.
AzidocillinThe serum concentration of Kanamycin can be decreased when it is combined with Azidocillin.
AzlocillinThe serum concentration of Kanamycin can be decreased when it is combined with Azlocillin.
BacampicillinThe serum concentration of Kanamycin can be decreased when it is combined with Bacampicillin.
BacitracinKanamycin may increase the nephrotoxic activities of Bacitracin.
BenzylpenicillinThe serum concentration of Kanamycin can be decreased when it is combined with Benzylpenicillin.
Botulinum Toxin Type AKanamycin may increase the neuromuscular blocking activities of Botulinum Toxin Type A.
Botulinum Toxin Type BKanamycin may increase the neuromuscular blocking activities of Botulinum Toxin Type B.
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Kanamycin.
CapreomycinCapreomycin may increase the neuromuscular blocking activities of Kanamycin.
CarbenicillinThe serum concentration of Kanamycin can be decreased when it is combined with Carbenicillin.
CarboplatinKanamycin may increase the ototoxic activities of Carboplatin.
CefaclorCefaclor may increase the nephrotoxic activities of Kanamycin.
CefdinirCefdinir may increase the nephrotoxic activities of Kanamycin.
CefepimeCefepime may increase the nephrotoxic activities of Kanamycin.
CefiximeCefixime may increase the nephrotoxic activities of Kanamycin.
CefmenoximeCefmenoxime may increase the nephrotoxic activities of Kanamycin.
CefotaximeCefotaxime may increase the nephrotoxic activities of Kanamycin.
CefotetanCefotetan may increase the nephrotoxic activities of Kanamycin.
CefoxitinCefoxitin may increase the nephrotoxic activities of Kanamycin.
CefpodoximeCefpodoxime may increase the nephrotoxic activities of Kanamycin.
CefprozilCefprozil may increase the nephrotoxic activities of Kanamycin.
CeftazidimeCeftazidime may increase the nephrotoxic activities of Kanamycin.
CeftibutenCeftibuten may increase the nephrotoxic activities of Kanamycin.
CeftriaxoneCeftriaxone may increase the nephrotoxic activities of Kanamycin.
CefuroximeCefuroxime may increase the nephrotoxic activities of Kanamycin.
CelecoxibCelecoxib may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
Cisatracurium besylateKanamycin may increase the activities of Cisatracurium besylate.
CisplatinCisplatin may increase the nephrotoxic activities of Kanamycin.
ClavulanateThe serum concentration of Kanamycin can be decreased when it is combined with Clavulanate.
ClodronateKanamycin may increase the activities of Clodronate.
CloxacillinThe serum concentration of Kanamycin can be decreased when it is combined with Cloxacillin.
ColistimethateKanamycin may increase the nephrotoxic activities of Colistimethate.
ColistinKanamycin may increase the nephrotoxic activities of Colistin.
CyclacillinThe serum concentration of Kanamycin can be decreased when it is combined with Cyclacillin.
CyclosporineKanamycin may increase the nephrotoxic activities of Cyclosporine.
DiclofenacDiclofenac may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
DicloxacillinThe serum concentration of Kanamycin can be decreased when it is combined with Dicloxacillin.
DiflunisalDiflunisal may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
DigoxinThe serum concentration of Digoxin can be decreased when it is combined with Kanamycin.
Etacrynic acidThe risk or severity of adverse effects can be increased when Ethacrynic acid is combined with Kanamycin.
EtodolacEtodolac may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
FenoprofenFenoprofen may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
FloctafenineFloctafenine may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
FlucloxacillinThe serum concentration of Kanamycin can be decreased when it is combined with Flucloxacillin.
FlurbiprofenFlurbiprofen may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
FoscarnetFoscarnet may increase the nephrotoxic activities of Kanamycin.
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Kanamycin.
HetacillinThe serum concentration of Kanamycin can be decreased when it is combined with Hetacillin.
IbandronateKanamycin may increase the activities of Ibandronate.
IbuprofenIbuprofen may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
IndomethacinIndomethacin may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
InfliximabInfliximab may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
KetoprofenKetoprofen may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
KetorolacKetorolac may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
MannitolMannitol may increase the nephrotoxic activities of Kanamycin.
MecamylamineKanamycin may increase the neuromuscular blocking activities of Mecamylamine.
Mefenamic acidMefenamic acid may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
MeloxicamMeloxicam may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
MeticillinThe serum concentration of Kanamycin can be decreased when it is combined with Meticillin.
MezlocillinThe serum concentration of Kanamycin can be decreased when it is combined with Mezlocillin.
NabumetoneNabumetone may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
NafcillinThe serum concentration of Kanamycin can be decreased when it is combined with Nafcillin.
NaproxenNaproxen may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
OxacillinThe serum concentration of Kanamycin can be decreased when it is combined with Oxacillin.
OxaprozinOxaprozin may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
PamidronateKanamycin may increase the activities of Pamidronate.
PancuroniumKanamycin may increase the activities of Pancuronium.
PhenoxymethylpenicillinThe serum concentration of Kanamycin can be decreased when it is combined with Phenoxymethylpenicillin.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Kanamycin.
PiperacillinThe serum concentration of Kanamycin can be decreased when it is combined with Piperacillin.
PiroxicamPiroxicam may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
PivampicillinThe serum concentration of Kanamycin can be decreased when it is combined with Pivampicillin.
PivmecillinamThe serum concentration of Kanamycin can be decreased when it is combined with Pivmecillinam.
RisedronateKanamycin may increase the activities of Risedronate.
RocuroniumKanamycin may increase the activities of Rocuronium.
SuccinylcholineKanamycin may increase the activities of Succinylcholine.
SulindacSulindac may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
TenofovirThe serum concentration of Kanamycin can be increased when it is combined with Tenofovir.
Tiaprofenic acidTiaprofenic acid may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
TicarcillinThe serum concentration of Kanamycin can be decreased when it is combined with Ticarcillin.
TiludronateKanamycin may increase the activities of Tiludronate.
TolmetinTolmetin may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Kanamycin.
VancomycinVancomycin may increase the nephrotoxic activities of Kanamycin.
VecuroniumKanamycin may increase the activities of Vecuronium.
Zoledronic acidKanamycin may increase the activities of Zoledronate.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Trna binding
Specific Function:
With S4 and S5 plays an important role in translational accuracy.Interacts with and stabilizes bases of the 16S rRNA that are involved in tRNA selection in the A site and with the mRNA backbone. Located at the interface of the 30S and 50S subunits, it traverses the body of the 30S subunit contacting proteins on the other side and probably holding the rRNA structure together. The combined cluste...
Gene Name:
rpsL
Uniprot ID:
P0A7S3
Molecular Weight:
13736.995 Da
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:17139284 ]
  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:17016423 ]
  3. Stavropoulos TA, Strathdee CA: Synergy between tetA and rpsL provides high-stringency positive and negative selection in bacterial artificial chromosome vectors. Genomics. 2001 Feb 15;72(1):99-104. [PubMed:11247671 ]
  4. Gondo Y, Shioyama Y, Nakao K, Katsuki M: A novel positive detection system of in vivo mutations in rpsL (strA) transgenic mice. Mutat Res. 1996 May 17;360(1):1-14. [PubMed:8657204 ]
  5. Amanuma K, Takeda H, Amanuma H, Aoki Y: Transgenic zebrafish for detecting mutations caused by compounds in aquatic environments. Nat Biotechnol. 2000 Jan;18(1):62-5. [PubMed:10625393 ]
2. 16S rRNA
Kind
Nucleotide
Organism
Enteric bacteria and other eubacteria
Pharmacological action
yes
Actions
inhibitor
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:17139284 ]
  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:17016423 ]
  3. Roy U, Nair D: Biodiversity of organotin resistant Pseudomonas from west coast of India. Ecotoxicology. 2007 Mar;16(2):253-61. Epub 2006 Nov 28. [PubMed:17131180 ]
  4. Pikuta EV, Hoover RB, Bej AK, Marsic D, Whitman WB, Krader PE, Tang J: Trichococcus patagoniensis sp. nov., a facultative anaerobe that grows at -5 degrees C, isolated from penguin guano in Chilean Patagonia. Int J Syst Evol Microbiol. 2006 Sep;56(Pt 9):2055-62. [PubMed:16957099 ]
  5. Chung JH, Park YS, Kim J, Shin GW, Nam MH, Oh MK, Kim CW, Jung GY, Hyun Park J: Parallel analysis of antimicrobial activities in microbial community by SSCP based on CE. Electrophoresis. 2007 Jul;28(14):2416-23. [PubMed:17577886 ]

Enzymes

Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
unknown
General Function:
Involved in N-acetyltransferase activity
Specific Function:
Catalyzes the coenzyme A-dependent acetylation of the 2' hydroxyl or amino group of a broad spectrum of aminoglycosides. It confers resistance to aminoglycosides
Gene Name:
aac
Uniprot ID:
P0A5N0
Molecular Weight:
20038.0 Da
References
  1. Vetting MW, Hegde SS, Javid-Majd F, Blanchard JS, Roderick SL: Aminoglycoside 2'-N-acetyltransferase from Mycobacterium tuberculosis in complex with coenzyme A and aminoglycoside substrates. Nat Struct Biol. 2002 Sep;9(9):653-8. [PubMed:12161746 ]
Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
unknown
General Function:
Nucleotidyltransferase activity
Specific Function:
Inactivates the antibiotic kanamycin by catalyzing the transfer of a nucleotidyl group from nucleoside triphosphates such as ATP to the 4'-hydroxyl group of the aminoglycoside.
Gene Name:
knt
Uniprot ID:
P05057
Molecular Weight:
28797.38 Da
References
  1. Gates CA, Northrop DB: Substrate specificities and structure-activity relationships for the nucleotidylation of antibiotics catalyzed by aminoglycoside nucleotidyltransferase 2''-I. Biochemistry. 1988 May 17;27(10):3820-5. [PubMed:2841975 ]
Kind
Protein
Organism
Escherichia coli
Pharmacological action
unknown
General Function:
Kanamycin kinase activity
Specific Function:
Resistance to kanamycin and structurally-related aminoglycosides, including amikacin.
Gene Name:
aphA1
Uniprot ID:
P00551
Molecular Weight:
30960.85 Da
References
  1. Wieninger SA, Serpersu EH, Ullmann GM: ATP binding enables broad antibiotic selectivity of aminoglycoside phosphotransferase(3')-IIIa: an elastic network analysis. J Mol Biol. 2011 Jun 10;409(3):450-65. doi: 10.1016/j.jmb.2011.03.061. Epub 2011 Apr 6. [PubMed:21477597 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on April 10, 2014 18:31