User:Mr. Ibrahem/Amikacin

Mr. Ibrahem/Amikacin
Clinical data
Trade names	Amikin, Amiglyde-V, Arikayce, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682661
License data	US DailyMed: Amikacin;
Pregnancy; category	AU: D; ;
Routes of; administration	intramuscular, intravenous
Drug class	Aminoglycoside
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	>90%
Protein binding	0–11%
Metabolism	Mostly unmetabolized
Elimination half-life	2–3 hours
Excretion	kidney
Identifiers
	IUPAC name (2S)-4-Amino-N-[(2S,3S,4R,5S)-5-amino-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2R,3R,4S,5R,6R)-6-(aminomethyl)-3,4,5-trihydroxy-oxan-2-yl]oxy-3-hydroxy-cyclohexyl]-2-hydroxybutanamide;
Chemical and physical data
Formula	C22H43N5O13
Molar mass	585.608 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(N[C@H]3[C@H](O[C@H]1O[C@@H]([C@@H](O)[C@H](N)[C@H]1O)CO)[C@@H](O)[C@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](N)C3)[C@@H](O)CCN;
	InChI InChI=1S/C22H43N5O13/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+/m0/s1 ; Key:LKCWBDHBTVXHDL-RMDFUYIESA-N ;
	(verify)

Amikacin is an antibiotic used for a number of bacterial infections.^[4] This includes joint infections, intra-abdominal infections, meningitis, pneumonia, sepsis, and urinary tract infections.^[4] It is also used for the treatment of multidrug-resistant tuberculosis.^[6] It is used by injection into a vein using an IV or into a muscle.^[4]

Amikacin, like other aminoglycoside antibiotics, can cause hearing loss, balance problems, and kidney problems.^[4] Other side effects include paralysis, resulting in the inability to breathe.^[4] If used during pregnancy it may cause permanent deafness in the baby.^[4]^[1] Amikacin works by blocking the function of the bacteria's 30S ribosomal subunit, making it unable to produce proteins.^[4]

Amikacin was patented in 1971, and came into commercial use in 1976.^[7]^[8] It is on the World Health Organization's List of Essential Medicines.^[9] The wholesale cost in the developing world is 13.80 to US$130.50 for a month.^[10] In the United States a typical course of treatment costs 25 to US$50.^[11] It is derived from kanamycin.^[4]

References

^ ^a ^b ^c "Amikacin Use During Pregnancy". Drugs.com. 2 December 2019. Archived from the original on 25 July 2020. Retrieved 13 March 2020.
^ "Amikacin 250 mg/ml Injection - Summary of Product Characteristics (SmPC)". (emc). 16 September 2015. Archived from the original on 13 March 2020. Retrieved 13 March 2020.
^ Plumb, Donald C. (2011). "Amikacin Sulfate". Plumb's Veterinary Drug Handbook (7th ed.). Stockholm, Wisconsin; Ames, Iowa: Wiley. pp. 39–43. ISBN 978-0-470-95964-0.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "Amikacin Sulfate". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
^ Cite error: The named reference who was invoked but never defined (see the help page).
^ World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 137. hdl:10665/44053. ISBN 9789241547659.
^ Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 507. ISBN 9783527607495. Archived from the original on 20 December 2016.
^ Oxford Handbook of Infectious Diseases and Microbiology. OUP Oxford. 2009. p. 56. ISBN 9780191039621. Archived from the original on 24 November 2015.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^ "Amikacin Sulfate". International Drug Price Indicator Guide. Archived from the original on 22 July 2018. Retrieved 8 December 2016.
^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 35. ISBN 9781284057560.

[Drugs.com_pregnancy-1] "Amikacin Use During Pregnancy". Drugs.com. 2 December 2019. Archived from the original on 25 July 2020. Retrieved 13 March 2020.

[2] "Amikacin 250 mg/ml Injection - Summary of Product Characteristics (SmPC)". (emc). 16 September 2015. Archived from the original on 13 March 2020. Retrieved 13 March 2020.

[plumb-3] Plumb, Donald C. (2011). "Amikacin Sulfate". Plumb's Veterinary Drug Handbook (7th ed.). Stockholm, Wisconsin; Ames, Iowa: Wiley. pp. 39–43. ISBN 978-0-470-95964-0.

[AHFS2016-4] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "Amikacin Sulfate". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.

[who-5] Cite error: The named reference who was invoked but never defined (see the help page).

[WHO2008-6] World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 137. hdl:10665/44053. ISBN 9789241547659.

[7] Fischer, Janos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 507. ISBN 9783527607495. Archived from the original on 20 December 2016.

[8] Oxford Handbook of Infectious Diseases and Microbiology. OUP Oxford. 2009. p. 56. ISBN 9780191039621. Archived from the original on 24 November 2015.

[WHO21st-9] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[ERC2014-10] "Amikacin Sulfate". International Drug Price Indicator Guide. Archived from the original on 22 July 2018. Retrieved 8 December 2016.

[Ric2015-11] Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 35. ISBN 9781284057560.

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