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Kanamycin sulfate(CAS No. 25389-94-0)

Kanamycin sulfate C18H36N4O11•H2O4S (cas 25389-94-0) Molecular Structure

25389-94-0 Structure

Identification and Related Records

【Name】
Kanamycin sulfate
【CAS Registry number】
25389-94-0
【Synonyms】
Kanamycin Mono Sulfate
Kanamycin Mono Sulphate
Prestwick_596
Otokalixin
Kanacedin
Kantrex
Kanabristol
Cantrex
Kanatrol
Kanaqua
Kantrex (TN)
Kanescin
Ophtalmokalixan
Cristalomicina
Kannasyn
Klebcil
133-92-6
Kanasig
Kanamytrex
Kantrim
2-(aminomethyl)-6-[4,6-diamino-3-[4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxy-cyclohexyl]oxy-oxane-3,4,5-triol
sulfuric acid
【EINECS(EC#)】
246-933-9
【Molecular Formula】
C18H36N4O11•H2O4S (Products with the same molecular formula)
【Molecular Weight】
582.66
【Inchi】
InChI=1S/C18H36N4O11.H2O4S/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;1-5(2,3)4/h4-18,23-29H,1-3,19-22H2;(H2,1,2,3,4)
【Canonical SMILES】
C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)O)O)OC3C(C(C(C(O3)CO)O)N)O)N.OS(=O)(=O)O
【MOL File】
25389-94-0.mol

Chemical and Physical Properties

【Appearance】
Off-white powder
【Melting Point】
250 oC
【Boiling Point】
943.2 °C at 760 mmHg
【Refractive Index】
117.5 ° (C=1, H2O)
【Flash Point】
524.2 °C
【Color/Form】
CRYSTALS FROM METHANOL + ETHANOL
【Stability】
Stable under normal temperatures and pressures.
【Storage temp】
2-8°C
【Spectral properties】
SPECIFIC OPTICAL ROTATION (0.1 N H2SO4): +146 DEG @ 24 DEG C/D
【Computed Properties】
Molecular Weight:582.57712 [g/mol]
Molecular Formula:C18H38N4O15S
H-Bond Donor:13
H-Bond Acceptor:19
Rotatable Bond Count:6
Exact Mass:582.205437
MonoIsotopic Mass:582.205437
Topological Polar Surface Area:366
Heavy Atom Count:38
Formal Charge:0
Complexity:720
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:15
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:2

Safety and Handling

【Hazard Codes】
T
【Risk Statements】
R61
【Safety Statements 】
22-24/25-45
【Safety】
A poison by intravenous route. Moderately toxic by intraperitoneal, subcutaneous, and intramuscular routes. Human systemic effects: hearing acuity changes. When heated to decomposition it emits very toxic NOx and SOx. See also KANAMYCIN SULFATE (1:1) SALT.
【Formulations/Preparations】
KANAMYCIN SULFATE, USP (KANTREX), IS AVAILABLE AS OFFICIAL INJECTION IN VIALS CONTAINING 500 MG IN 2-ML OR 1.0 G IN 3-ML VOL, IN PEDIATRIC VIALS (75 MG/2 ML), & FOR ORAL USE IN OFFICIAL CAPSULES CONTAINING 500 MG.
USP REQUIRES THAT KANAMYCIN SULFATE CONTAINS NOT LESS THAN 75% KANAMYCIN A & NOT MORE THAN 5% KANAMYCIN B SULFATE ON ANHYD BASIS. /SULFATE/
USP /Sulfate/
【Exposure Standards and Regulations】
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

ANTIBIOTIC COMPLEX PRODUCED BY STREPTOMYCES KANAMYCETICUS OKAMI & UMEZAWA FROM JAPANESE SOIL
【Usage】

Antibiotic.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances that reduce the growth or reproduction of BACTERIA.
- Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.
【Therapeutic Uses】
Antibiotics, Aminoglycoside; Antibiotics, Antitubercular
/KANAMYCIN IS ANTIBIOTIC WHICH/...HAS BROAD RANGE OF ACTIVITY AGAINST GRAM-POSITIVE & GRAM-NEGATIVE MICROORGANISMS. SENSITIVE BACTERIA INCL E COLI, ENTEROBACTER (AEROBACTER) AEROGENES, K PNEUMONIAE, PROTEUS SPECIES, CITROBACTER...SALMONELLA, SHIGELLA, VIBRIO, NEISSERIA, BRUCELLA, M TUBERCULOSIS, ATYPICAL MYCOBACTERIA...
AMONG INFECTIONS DUE TO GRAM-POSITIVE BACTERIA, ONLY THOSE CAUSED BY STAPH AUREUS BENEFIT SIGNIFICANTLY... WITH...LESS TOXIC.../DRUGS/ THERE IS...LITTLE NEED FOR...KANAMYCIN IN MGMNT OF THIS KIND OF DISEASE. HOWEVER, IT MAY BE NECESSARY TO TREAT METHICILLIN-RESISTANT STRAINS WITH CONJOINT OF CEPHALOSPORIN & KANAMYCIN.
MOST STRAINS OF STAPHYLOCOCCI ARE INHIBITED BY 1 UG/ML OR LESS; SOME ARE SUPPRESSED ONLY BY CONCN OF 2-5 UG/ML. TUBERCLE BACILLI ARE SUPPRESSED BY 2.5-10 UG/ML. PNEUMOCOCCI, ALCALIGENES, & STREP PYOGENES ARE GENERALLY INSENSITIVE.
KANAMYCIN HAS BEEN EMPLOYED TO TREAT HUMAN TUBERCULOSIS IN COMBINATION WITH OTHER EFFECTIVE DRUGS. BECAUSE THE THERAPY OF THIS DISEASE IS PROTRACTED & INVOLVES ADMIN OF LARGE TOTAL DOSES OF DRUG, WITH RISK OF OTOTOXICITY & NEPHROTOXICITY, /IT/ SHOULD BE USED ONLY TO TREAT PATIENTS WHO HARBOR MICROORGANISMS THAT ARE RESISTANT TO THE MORE COMMONLY USED AGENTS.
KANAMYCIN HAS BEEN ADMIN ORALLY TO SUPPRESS INTESTINAL FLORA PRIOR TO SURGERY & AS ADJUNCT THERAPY IN CASES OF HEPATIC COMA. ... EFFECT ON INTESTINAL BACTERIA MAY NOT BE SUSTAINED EVEN WHEN SUCH LARGE DOSES...ARE ADMIN.
Kanamycin is indicated in the treatment of biliary tract infections caused by susceptible organisms. /Included in US product labeling/
Kanamycin is indicated in the treatment of bone and joint infections caused by susceptible organisms. /Included in US product labeling/
Kanamycin is indicated in the treatment of central nervous system infections caused by susceptible organisms. /Included in US product labeling/
Kanamycin is indicated in the treatment of intra-abdominal infections caused by susceptible organisms. /Included in US product labeling/
Kanamycin is indicated in the treatment of bacterial, gram-negative pneumonia caused by susceptible organisms. /Included in US product labeling/
Kanamycin is indicated in the treatment of bacterial septicemia caused by susceptible organisms. /Included in US product labeling/
Kanamycin is indicated in the treatment of skin and soft tissue infections caused by susceptible organisms. /Included in US product labeling/
Kanamycin is indicated in the treatment of recurrent complicated urinary tract infections caused by susceptible organisms. /Included in US product labeling/
Kanamycin use has declined over the years due to the emergence of a large number of resistant organisms. However, because of its disuse, resistance has decreased in some areas.
Aminoglycoside are indicated in the treatment of serious systemic infections for which less toxic antibacterials are ineffective or contraindicated. The spectrum of aminoglycosides covers aerobic gram-negative bacilli, and some gram-positive organisms. They are not active against anaerobic organisms. /Aminoglycosides/
The antibacterial activity of aminoglycosides against different strains of organisms varies among institutions and regions. However, aminoglycosides are generally active against most Enterobacteriaceae, including Escherichia coli, Proteus mirabilis, indole-positive Proteus, Citrobacter, Enterobacter, Klebsiella, Providencia, and Serratia species. Acinetobacter and Pseudomonas species are also usually susceptible. ... Aminoglycosides are used concurrently with antipseudomonal penicillins or certain cephalosporins in the treatment of serious Pseudomonas aeruginosa infections. /Aminoglycosides/
Aminoglycosides are also active against Staphylococcus aureus, but are rarely used as sole therapy since other, less toxic, antibiotics are available. /Aminoglycosides/
Aminoglycosides are indicated for the treatment of serious infections caused by, or strongly suspected to be caused by, susceptible gram-negative bacilli. ... Aminoglycosides are used to treat central nervous system (CNS) infections mainly in neonates due to better penetration across the blood-brain barrier in this age group; ... . Aminoglycosides are also used in combination with other antibacterials for a possible synergistic effect. /Aminoglycosides/
VET: Antibacterial
【Biomedical Effects and Toxicity】
KANAMYCIN IS EXCRETED PRIMARILY BY KIDNEY, MOSTLY BY GLOMERULAR FILTRATION, BUT SOME IS SECRETED BY TUBULES. ONLY 0.3-1.5% OF INGESTED DOSE IS EXCRETED IN URINE BECAUSE OF POOR ENTERIC ABSORPTION. FROM 40-80% OF PARENTERAL DOSE IS RECOVERABLE IN URINE IN 24-HR PERIOD AFTER INJECTION.
KANAMYCIN IS POORLY ABSORBED FROM GI TRACT, & MOST OF INGESTED DOSE IS ELIMINATED IN FECES; VERY LOW PLASMA CONCN ARE DETECTABLE AFTER ORAL MEDICATION IN SOME INDIVIDUALS.
PLASMA CONCN OF DRUG AFTER IM INJECTION ARE ADEQUATELY DESCRIBED BY ONE-COMPARTMENT MODEL CHARACTERIZED BY ELIMINATION HALF-LIFE OF 2 2/5 HR & VOL OF DISTRIBUTION APPROX 40% OF TOTAL BODY WATER. ABSORPTION FROM IM DEPOT IS COMPLETE IN ABOUT 1 1/2 HR.
IM INJECTION OF 1 G...YIELDS PEAK PLASMA CONCN OF 20-35 UG/ML @ ABOUT 1 HR; THIS FALLS TO 1.2 UG/ML OR LESS @ 12 HR. HALF-LIFE OF DRUG IN PREMATURE INFANTS LESS THAN 2 DAYS OLD IS 18 HR; IN BABIES 5-22 DAYS OF AGE, 6 HR.
VERY LOW CONCN...ARE PRESENT IN FECES AFTER PARENTERAL INJECTION...
PARENTERAL ADMIN...RESULTS IN APPEARANCE OF APPRECIABLE CONCN...IN PLEURAL, ASCITIC, SYNOVIAL, & PERITONEAL FLUIDS. IN ADULT, VERY LITTLE ANTIBIOTIC IS DETECTED IN CEREBROSPINAL FLUID. IM INJECTION...IN NORMAL CHILDREN PRODUCES SPINAL FLUID CONCN, AFTER 3 HR, THAT AVG 1/5-TO 1/10 OF THOSE SIMULTANEOUSLY PRESENT IN PLASMA...
...KANAMYCIN CONCN IN CEREBROSPINAL FLUID OF NEWBORN INFANTS WITH BACTERIAL MENINGITIS GIVEN 7.5 MG/KG IM SUGGEST THAT COMPLETE CONFIDENCE IN USE OF THIS AGENT IN SUCH PT MAY NOT BE JUSTIFIED... ANTIBIOTIC DIFFUSES POORLY INTO BILE & AMNIOTIC & PROSTATIC FLUIDS...
Approximately 1% of an oral dose of kanamycin is absorbed from the normal GI tract.
In adults with normal renal function, 80-90% of a single IM dose of kanamycin is excreted unchanged by glomerular filtration within 24 hours. Complete recovery of the dose in urine requires approximately 10-20 days in patients with normal renal function. Following oral administration, unabsorbed kanamycin is excreted unchanged in the feces and that portion of the dose which is absorbed is excreted unchanged in the urine.

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