Amikacin

Structural formula
General
Non-proprietary name	Amikacin
other names	(2 S ) -4-amino- N - [(2 S , 3 S , 4 R , 5 S ) -5-amino-2 - [(2 S , 3 R , 4 S , 5 S , 6 R ) - 4-amino-3,5-dihydroxy-6- (hydroxymethyl) oxan-2-yl] oxy-4 - [(2 R , 3 R , 4 S , 5 R , 6 R ) -6- (aminomethyl) -3 , 4,5-trihydroxy-oxan-2-yl] oxy-3-hydroxy-cyclohexyl] -2-hydroxy-butanamide ( IUPAC )
Molecular formula	C 22 H 43 N 5 O 13
Brief description	White dust
External identifiers / databases
CAS number 37517-28-5 EC number 253-538-5 ECHA InfoCard 100,048,653 PubChem 37768 DrugBank DB00479 Wikidata Q408529
Drug information
ATC code	D06 AX12 , J01 GB06 , S01 AA21
Drug class	Aminoglycoside antibiotic
properties
Molar mass	585.6 g · mol -1
solubility	soluble in water (50 g · l −1 ), slightly soluble in methanol , not soluble in ethanol
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
Toxicological data	280 mg kg −1 ( LD 50 ,  mouse ,  iv )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Amikacin is an antibiotic from the group of aminoglycosides that has a bactericidal effect against gram-negative aerobic germs .

application

Amikacin is used to treat severe infections caused by sensitive gram-negative pathogens, especially of the genera Pseudomonas , Escherichia coli , Proteus , Providencia , Klebsiella , Enterobacter , Serratia , Mycobacterium , Nocardia and Acinetobacter . As monotherapy, it is mostly used for upper urinary tract infections and soft tissue infections. For the initial treatment of sepsis or infections in immunosuppressed patients (e.g. after chemotherapy), amikacin is used in combination with other agents, mostly with β-lactam antibiotics (synergistic effect especially with piperacillin ).

Amikacin is still used as a replacement aminoglycoside for the more common streptomycin for the treatment of multi-resistant tuberculosis pathogens (mycobacterium tuberculosis). It is a second-choice drug for this purpose, used only in combination with other anti-tuberculotics in the event of therapy failure with the classic therapy schemes. Amikacin is listed by the World Health Organization as one of the complementary "second line" drugs in the list of essential drugs .

Pharmacodynamics (mechanism of action)

As an aminoglycoside, amikacin inhibits bacterial protein synthesis by blocking the function of the ribosomes . Among other things, it prevents the translocation of peptidyl- tRNA and thus the initiation of protein synthesis.

Pharmacokinetics and Interactions

In peroral done absorption of amikacin - as with all aminoglycosides - no absorption from the gut, which is why the drug parenterally be as an intramuscular injection or administered by intravenous infusion needs. Amikacin only crosses the blood-brain barrier in the presence of inflammatory disorders. Amikacin is not metabolized in the liver but is excreted unchanged through the kidneys.

If other potentially ototoxic drugs are administered at the same time, such as platinum-containing cytostatics and loop diuretics , the ototoxic effect can be increased. The duration of action of non-depolarizing muscle relaxants may be prolonged.

Side effects

Very often there is a disturbance of the kidney function with reduced glomerular filtration ( nephrotoxicity ). Injection site pain, proteinuria, and plasma electrolyte imbalances are common, especially hypokalaemia , hypocalcemia, and hypomagnesaemia . Occasionally there is dose and duration-dependent hearing impairment, tinnitus and dizziness due to damage to the vestibulocochlear nerve ( ototoxicity ) and peripheral nerve damage (which can be irreversible), as well as an increase in life enzymes and skin rashes. Changes in the blood count ( thrombocytopenia , leukopenia , eosinophilia ) and skin rashes rarely occur . Very rarely to polyneuropathies and acute kidney failure.

Contraindications

A contraindication is given during pregnancy, as possible deafness of the child cannot be ruled out. There is also a contraindication for use in premature and newborn babies. With kidney, liver and hearing damage as well as balance disorders, as with myasthenia gravis and Parkinson's disease, caution is advised. In end-stage renal failure and previous damage to the inner ear or organ of equilibrium, amikacin may only be administered if there is a vital indication. Although damage to the liver has no effect on the plasma level, a hepatorenal syndrome can develop .

Trade names

Amikacin ; Biklin ; Amikin

literature

• WHO: Guidelines for the programmatic management of drug-resistant tuberculosis. (PDF; 1.3 MB) 2006. ISBN 978-92-4-154695-9 , pp. 127–128.
• Marianne Abele-Horn: Antimicrobial Therapy. Decision support for the treatment and prophylaxis of infectious diseases. With the collaboration of Werner Heinz, Hartwig Klinker, Johann Schurz and August Stich, 2nd, revised and expanded edition. Peter Wiehl, Marburg 2009, ISBN 978-3-927219-14-4 , p. 338.

Web links

• Institute for Clinical Chemistry and Pathobiochemistry at Klinikum rechts der Isar: Short version of aminoglycosides, including Amikacin ( Memento from March 2, 2014 in the Internet Archive )

Individual evidence

1. ↑ ^{a b c} AMIKACIN CRS data sheet (PDF) at EDQM , accessed on December 21, 2009.
2. ↑ ^{a b} Amikacin dihydrate data sheet from Sigma-Aldrich , accessed on October 20, 2016 ( PDF ).
3. ↑ WHO Model List of Essential Medicines (PDF; 442 kB) , accessed on February 7, 2014.
4. ↑ See Marianne Abele-Horn: Antimicrobial Therapy. Decision support for the treatment and prophylaxis of infectious diseases. 2009, p. 338.
5. ↑ Marianne Abele-Horn (2009), p. 338.
6. ↑ Marianne Abele-Horn (2009), p. 338.

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !