Amikacin | CAS#37517-28-5 | antibiotic

MedKoo Cat#: 558063 | Name: Amikacin free base

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Amikacin is an aminoglycoside antibiotic derived from kanamycin A. Like other aminoglycosides, amikacin binds to bacterial ribosomes and disrupts translation.1 However, the specific binding sites differ between different aminoglycoside antibiotics, as do the mechanisms of resistance. Amikacin is effective against Gram-negative and Gram-positive bacteria.

Chemical Structure

Amikacin free base

CAS#37517-28-5 (free base)

Theoretical Analysis

MedKoo Cat#: 558063

Name: Amikacin free base

CAS#: 37517-28-5 (free base)

Chemical Formula: C22H43N5O13

Exact Mass: 585.2857

Molecular Weight: 585.61

Elemental Analysis: C, 45.12; H, 7.40; N, 11.96; O, 35.52

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
2g	USD 425.00	2 Weeks
5g	USD 750.00	2 Weeks
10g	USD 1,250.00	2 Weeks

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Related CAS #

37517-28-5 (free base) 39831-55-5 (sulfate) 1257517-67-1 (hydrate)

Synonym

Antibiotic BB-K 8; BAY 41-6551; BB-K 8; Lukadin; Potentox;

IUPAC/Chemical Name

(S)-4-amino-N-((1R,2S,3S,4R,5S)-5-amino-2-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4-(((2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-3-hydroxycyclohexyl)-2-hydroxybutanamide

InChi Key

LKCWBDHBTVXHDL-RMDFUYIESA-N

InChi Code

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

SMILES Code

NC[C@@H](O1)[C@@H](O)[C@H](O)[C@@H](O)[C@@]1([H])O[C@@H]2[C@@H](N)C[C@@H](NC([C@@H](O)CCN)=O)[C@H](O[C@@]3([H])O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H]2O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

An aminoglycoside antibiotic.

In vitro activity:

For Escherichia coli, including extended-spectrum beta-lactamase (ESBL)-producing isolates (45.7% of population), amikacin demonstrated excellent activity (93.0%–94.7% susceptible) similar to tigecycline, piperacillin/tazobactam, and the carbapenems. Against Klebsiella pneumoniae, only tigecycline retained susceptibility >90%; amikacin inhibited 83.7% and 71.1% of the total and ESBL-producing (24.2%) populations at its breakpoint, respectively. Reference: Infect Drug Resist. 2018; 11: 783–790. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5975598/

In vivo activity:

Macrophages engulfing amikacin-killed cells demonstrated a reduced release of pro-inflammatory cytokines (IL-1β, TNF-α, and IL-6) and a concomitant increased production of anti-inflammatory cytokines (TGF-β) (Figure 6). Similarly, amikacin-killed chondrocytes also induced more TGF-β than did heat-killed chondrocytes (p = 0.03). In contrast, less IL-1β was produced by macrophages incubated with amikacin-killed cells than by macrophages incubated with heat-killed cells (p = 0.006). Similar responses were noted for TNF-α (p < 0.0001) and IL-6 (p < 0.0001) production between amikacin- vs. heat-killed cells. These findings indicate that cell death induced by amikacin is inherently anti-inflammatory compared to the pathways associated with necrosis. These findings in vitro help explain why SF from amikacin-treated horses manifested a relatively benign response to ongoing cellular death and tissue injury locally within the joint. Reference: Front Vet Sci. 2021; 8: 676774. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8175670/

	Solvent	mg/mL	mM
Solubility
	PBS (pH 7.2)	5.0	8.54

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 585.61 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Kuti JL, Wang Q, Chen H, Li H, Wang H, Nicolau DP. Defining the potency of amikacin against Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, and Acinetobacter baumannii derived from Chinese hospitals using CLSI and inhalation-based breakpoints. Infect Drug Resist. 2018 May 25;11:783-790. doi: 10.2147/IDR.S161636. PMID: 29872328; PMCID: PMC5975598. 2. Sutherland CA, Verastegui JE, Nicolau DP. In vitro potency of amikacin and comparators against E. coli, K. pneumoniae and P. aeruginosa respiratory and blood isolates. Ann Clin Microbiol Antimicrob. 2016 Jun 17;15(1):39. doi: 10.1186/s12941-016-0155-z. PMID: 27316973; PMCID: PMC4912699. 3. Pezzanite L, Chow L, Hendrickson D, Gustafson DL, Russell Moore A, Stoneback J, Griffenhagen GM, Piquini G, Phillips J, Lunghofer P, Dow S, Goodrich LR. Evaluation of Intra-Articular Amikacin Administration in an Equine Non-inflammatory Joint Model to Identify Effective Bactericidal Concentrations While Minimizing Cytotoxicity. Front Vet Sci. 2021 May 21;8:676774. doi: 10.3389/fvets.2021.676774. PMID: 34095281; PMCID: PMC8175670. 4. Bugnon D, Potel G, Xiong YQ, Caillon J, Kergueris MF, Le Conte P, Baron D, Drugeon H. In vivo antibacterial effects of simulated human serum profiles of once-daily versus thrice-daily dosing of amikacin in a Serratia marcescens endocarditis experimental model. Antimicrob Agents Chemother. 1996 May;40(5):1164-9. doi: 10.1128/AAC.40.5.1164. PMID: 8723459; PMCID: PMC163284.

In vitro protocol:

In vivo protocol:

1. Pezzanite L, Chow L, Hendrickson D, Gustafson DL, Russell Moore A, Stoneback J, Griffenhagen GM, Piquini G, Phillips J, Lunghofer P, Dow S, Goodrich LR. Evaluation of Intra-Articular Amikacin Administration in an Equine Non-inflammatory Joint Model to Identify Effective Bactericidal Concentrations While Minimizing Cytotoxicity. Front Vet Sci. 2021 May 21;8:676774. doi: 10.3389/fvets.2021.676774. PMID: 34095281; PMCID: PMC8175670. 2. Bugnon D, Potel G, Xiong YQ, Caillon J, Kergueris MF, Le Conte P, Baron D, Drugeon H. In vivo antibacterial effects of simulated human serum profiles of once-daily versus thrice-daily dosing of amikacin in a Serratia marcescens endocarditis experimental model. Antimicrob Agents Chemother. 1996 May;40(5):1164-9. doi: 10.1128/AAC.40.5.1164. PMID: 8723459; PMCID: PMC163284.

1: Rose SJ, Neville ME, Gupta R, Bermudez LE. Delivery of aerosolized liposomal amikacin as a novel approach for the treatment of nontuberculous mycobacteria in an experimental model of pulmonary infection. PLoS One. 2014 Sep 29;9(9):e108703. doi: 10.1371/journal.pone.0108703. eCollection 2014. PubMed PMID: 25264757; PubMed Central PMCID: PMC4180930. 2: Zantingh AJ, Schwark WS, Fubini SL, Watts AE. Accumulation of amikacin in synovial fluid after regional limb perfusion of amikacin sulfate alone and in combination with ticarcillin/clavulanate in horses. Vet Surg. 2014 Mar;43(3):282-8. doi: 10.1111/j.1532-950X.2014.12119.x. Epub 2014 Jan 27. PubMed PMID: 24467593. 3: Montgomery AB, Vallance S, Abuan T, Tservistas M, Davies A. A randomized double-blind placebo-controlled dose-escalation phase 1 study of aerosolized amikacin and fosfomycin delivered via the PARI investigational eFlow® inline nebulizer system in mechanically ventilated patients. J Aerosol Med Pulm Drug Deliv. 2014 Dec;27(6):441-8. doi: 10.1089/jamp.2013.1100. PubMed PMID: 24383962; PubMed Central PMCID: PMC4273204. 4: Dudek M, Romanowska J, Wituła T, Trylska J. Interactions of amikacin with the RNA model of the ribosomal A-site: computational, spectroscopic and calorimetric studies. Biochimie. 2014 Jul;102:188-202. doi: 10.1016/j.biochi.2014.03.009. Epub 2014 Apr 24. PubMed PMID: 24769038. 5: An SH, Kim JY, Gwak HS. Outcomes of a new dosage regimen of amikacin based on pharmacokinetic parameters of Korean neonates. Am J Health Syst Pharm. 2014 Jan 15;71(2):122-7. doi: 10.2146/ajhp130308. PubMed PMID: 24375604. 6: Pajot O, Burdet C, Couffignal C, Massias L, Armand-Lefevre L, Foucrier A, Da Silva D, Lasocki S, Laouénan C, Mentec H, Mentré F, Wolff M. Impact of imipenem and amikacin pharmacokinetic/pharmacodynamic parameters on microbiological outcome of Gram-negative bacilli ventilator-associated pneumonia. J Antimicrob Chemother. 2015 May;70(5):1487-94. doi: 10.1093/jac/dku569. Epub 2015 Jan 27. PubMed PMID: 25630642. 7: Burdet C, Pajot O, Couffignal C, Armand-Lefèvre L, Foucrier A, Laouénan C, Wolff M, Massias L, Mentré F. Population pharmacokinetics of single-dose amikacin in critically ill patients with suspected ventilator-associated pneumonia. Eur J Clin Pharmacol. 2015 Jan;71(1):75-83. doi: 10.1007/s00228-014-1766-y. Epub 2014 Oct 21. PubMed PMID: 25327505. 8: Bijleveld Y, de Haan T, Toersche J, Jorjani S, van der Lee J, Groenendaal F, Dijk P, van Heijst A, Gavilanes AW, de Jonge R, Dijkman KP, van Straaten H, Rijken M, Zonnenberg I, Cools F, Nuytemans D, Mathôt R. A simple quantitative method analysing amikacin, gentamicin, and vancomycin levels in human newborn plasma using ion-pair liquid chromatography/tandem mass spectrometry and its applicability to a clinical study. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Mar 1;951-952:110-8. doi: 10.1016/j.jchromb.2014.01.035. Epub 2014 Jan 30. PubMed PMID: 24548921. 9: De Rosa FG, Roberts JA. Amikacin dosing in the ICU: we now know more, but still not enough…. Intensive Care Med. 2014 Jul;40(7):1033-5. doi: 10.1007/s00134-014-3308-6. Epub 2014 May 10. PubMed PMID: 24817029. 10: Barrantes-González M, Grau S, Conde-Estévez D, Salas E, Marín-Casino M. [Influence of ethnicity on the pharmacokinetics of amikacin]. Rev Esp Quimioter. 2013 Dec;26(4):346-52. Spanish. PubMed PMID: 24399348. 11: Smits A, De Cock RF, Allegaert K, Vanhaesebrouck S, Danhof M, Knibbe CA. Prospective Evaluation of a Model-Based Dosing Regimen for Amikacin in Preterm and Term Neonates in Clinical Practice. Antimicrob Agents Chemother. 2015 Oct;59(10):6344-51. doi: 10.1128/AAC.01157-15. Epub 2015 Jul 27. PubMed PMID: 26248375; PubMed Central PMCID: PMC4576045. 12: Belotti S, Rossi A, Colombo P, Bettini R, Rekkas D, Politis S, Colombo G, Balducci AG, Buttini F. Spray dried amikacin powder for inhalation in cystic fibrosis patients: a quality by design approach for product construction. Int J Pharm. 2014 Aug 25;471(1-2):507-15. doi: 10.1016/j.ijpharm.2014.05.055. Epub 2014 Jun 2. PubMed PMID: 24886692. 13: Sole A, Nieto JE, Aristizabal FA, Snyder JR. Effect of emptying the vasculature before performing regional limb perfusion with amikacin in horses. Equine Vet J. 2016 Nov;48(6):737-740. doi: 10.1111/evj.12501. Epub 2015 Oct 6. PubMed PMID: 26278891. 14: So W, Crandon JL, Hamada Y, Nicolau DP. Antibacterial activity of achievable epithelial lining fluid exposures of Amikacin Inhale with or without meropenem. J Antimicrob Chemother. 2016 Feb;71(2):428-37. doi: 10.1093/jac/dkv370. Epub 2015 Nov 10. PubMed PMID: 26559690. 15: Fair RJ, McCoy LS, Hensler ME, Aguilar B, Nizet V, Tor Y. Singly modified amikacin and tobramycin derivatives show increased rRNA A-site binding and higher potency against resistant bacteria. ChemMedChem. 2014 Sep;9(9):2164-71. doi: 10.1002/cmdc.201402175. Epub 2014 Jul 23. PubMed PMID: 25055981; PubMed Central PMCID: PMC4298452. 16: Cho SY, Choi SM, Park SH, Lee DG, Choi JH, Yoo JH. Amikacin therapy for urinary tract infections caused by extended-spectrum β-lactamase-producing Escherichia coli. Korean J Intern Med. 2016 Jan;31(1):156-61. doi: 10.3904/kjim.2016.31.1.156. Epub 2015 Dec 28. PubMed PMID: 26767869; PubMed Central PMCID: PMC4712420. 17: Colbath AC, Wittenburg LA, Gold JR, McIlwraith CW, Moorman VJ. The Effects of Mepivacaine Hydrochloride on Antimicrobial Activity and Mechanical Nociceptive Threshold During Amikacin Sulfate Regional Limb Perfusion in the Horse. Vet Surg. 2016 Aug;45(6):798-803. doi: 10.1111/vsu.12515. Epub 2016 Jul 15. PubMed PMID: 27416788. 18: Varshosaz J, Ghaffari S, Mirshojaei SF, Jafarian A, Atyabi F, Kobarfard F, Azarmi S. Biodistribution of amikacin solid lipid nanoparticles after pulmonary delivery. Biomed Res Int. 2013;2013:136859. doi: 10.1155/2013/136859. Epub 2013 Aug 1. PubMed PMID: 23984315; PubMed Central PMCID: PMC3747341. 19: Nieto JE, Trela J, Stanley SD, Yamout S, Snyder JR. Pharmacokinetics of a combination of amikacin sulfate and penicillin G sodium for intravenous regional limb perfusion in adult horses. Can J Vet Res. 2016 Jul;80(3):230-5. PubMed PMID: 27408337; PubMed Central PMCID: PMC4924558. 20: Kacířová I, Grundmann M. [Therapeutic monitoring of amikacin and gentamicin in routine clinical practice]. Vnitr Lek. 2015 Jan;61(1):33-41. Czech. PubMed PMID: 25693614.