KANAMYCIN
- CAS NO.:59-01-8
- Empirical Formula: C18H36N4O11
- Molecular Weight: 484.5
- MDL number: MFCD00070289
- EINECS: 200-411-7
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-05 19:05:58
What is KANAMYCIN?
Absorption
Kanamycin 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.
Toxicity
Mild 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.
The Uses of KANAMYCIN
Kanamycin A is an antibiotic complex produced by Streptomyces kanamyceticus Okami & Umezawa from Japanese soil. Comprised of three components, kanamycin A, the major component, and kanamycins B and C, two minor congeners. Antibacterial.
The Uses of KANAMYCIN
Antibacterial Kantrex (Apothecon).
Background
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.
Indications
For 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.
Indications
Kanamycin, O-3-amino-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[6-deoxy-
6-amino-α-D-glucopyranosyl-(1→4)]–2-deoxy-D-streptamine (32.4.6), is isolated from a
culture fluid of the actinomycete Streptomyces kanamyceticus, which produces three
antibiotics—kanamycins A, B, and C.
Kanamycin A is similar to streptomycin and neomycines, and it possesses a broad spectrum of antimicrobial action. It is active with respect to most Gram-positive and Gramnegative microorganisms (staphylococci, colon bacillus, klebisella, Fridlender’s bacillus,
proteus, shigella, salmonella).
It is used to treat sepsis, meningitis, osteomyelitis, peritonitis, pneumonia, pyelonephritis, pyelocystitis, infected wounds, and post-operational, purulent complications that are
caused by microorganisms sensitive to this drug. Kanamycin is used to treat tuberculosis
of the lungs and other organs upon resistance to other antituberculosis drugs. Synonyms of
this drug are karmycin, kamaxin, resistomycin, and many others.
Definition
ChEBI: Kanamycin A is a member of kanamycins. It has a role as a bacterial metabolite. It is a conjugate base of a kanamycin A(4+).
brand name
Klebcil (King).
Antimicrobial activity
It is active against staphylococci, including methicillin-resistant strains. Other aerobic and anaerobic Gram-positive cocci and most Gram-positive rods are resistant, but M. tuberculosis is susceptible. It is widely active against most aerobic Gram-negative rods, except Burkholderia cepacia and Sten. maltophilia. Treponema pallidum, Leptospira and Mycoplasma spp. are all resistant.
Acquired resistance
Resistance is usually plasmid borne and due to enzymatic inactivation of the drug by enzymes that also inactivate gentamicin or tobramycin . Resistance due to reduced permeability is also encountered.
Pharmacokinetics
Kanamycin 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.
Pharmacokinetics
Cmax 500 mg intramuscular: c.15–20 mg/L after 1 h
Plasma half-life: 2.5 h
Volume of distribution: 0.3 L/kg
Plasma protein binding: Low
Absorption and distribution
Very little is absorbed from the intestinal tract. The peak plasma
concentration in the neonate is dose related: concentrations of
8–30 mg/L (mean 18 mg/L) have been found 1 h after a 10 mg/kg
dose. The drug is confined to the extracellular fluid. The concentration
in serous fluids is said to equal that in the plasma,
but it does not enter the CSF in therapeutically useful concentrations
even in the presence of meningeal inflammation.
Excretion
It is excreted almost entirely by the kidneys, almost exclusively
in the glomerular filtrate. Up to 80% of the dose appears
unchanged in the urine over the first 24 h, producing concentrations
around 100–500 mg/L. It is retained in proportion to
reduction in renal function. Less than 1% of the dose appears
in the bile. In patients receiving 500 mg intramuscularly preoperatively,
concentrations of 2–23 mg/L have been found in
bile and 8–14 mg/kg in gallbladder wall.
Clinical Use
Formerly used for severe infection with susceptible organisms, it has largely been superseded by other aminoglycosides.
Side Effects
Intramuscular injections are moderately painful, and minor
side effects similar to those encountered with streptomycin
have been described. Eosinophilia in the absence of other manifestations of allergy occurs in up to 10% of patients.
Other manifestations of hypersensitivity are rare.
As with other aminoglycosides, the most important toxic
effects are on the eighth nerve and much less frequently on
the kidney. Renal damage is seen principally in patients with
pre-existing renal disease or treated concurrently or sequentially
with other potentially nephrotoxic agents. The drug
accumulates in the renal cortex, producing cloudy swelling,
which may progress to acute necrosis of proximal tubular
cells with oliguric renal failure. Less dramatic deterioration
of renal function, particularly exaggeration of the potential
nephrotoxicity of other drugs or of existing renal disease, is
of principal importance because it increases the likelihood of
ototoxicity.
Vestibular damage is uncommon but may be severe and
prolonged. Hearing damage is usually bilateral, and typically
affects frequencies above the conversational range. Acute toxicity
is most likely in patients in whom the plasma concentration
exceeds 30 mg/L, but chronic toxicity may be seen in patients
treated with the drug over long periods. Auditory toxicity may
be potentiated by concurrent treatment with potent diuretics
like ethacrynic acid. If tinnitus – which usually heralds the onset
of auditory injury – develops, the drug should be withdrawn.
Neuromuscular blockade is seen particularly in patients
receiving other muscle relaxants or suffering from myasthenia
gravis and may be reversed by neostigmine.
Metabolism
Not Available
Properties of KANAMYCIN
Melting point: | >175°C (dec.) |
Boiling point: | 581.13°C (rough estimate) |
alpha | D24 +146° (0.1N H2SO4) |
Density | 1.4042 (rough estimate) |
refractive index | 1.6700 (estimate) |
storage temp. | 2-8°C |
solubility | Methanol (Slightly, Sonicated), Water (Slightly) |
form | liquid |
pka | pKa 6.40/7.55/8.40/9.40(H2O) (Uncertain) |
color | White to Off-White |
EPA Substance Registry System | D-Streptamine, O-3-amino-3-deoxy-.alpha.-D-glucopyranosyl-(1.fwdarw.6)-O-[6-amino-6-deoxy-.alpha.-D-glucopyranosyl-(1.fwdarw.4)]-2-deoxy- (59-01-8) |
Safety information for KANAMYCIN
Computed Descriptors for KANAMYCIN
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