Amikacin Sulfate | CAS#39831-55-5 | Antibiotic

MedKoo Cat#: 100955 | Name: Amikacin sulfate

Description:

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

Amikacin is an antibiotic used for a number of bacterial infections. This includes joint infections, intraabdominal infections, meningitis, pneumonia, sepsis, and urinary tract infections. It is also used for the treatment of multidrug-resistant tuberculosis. It is used either by injection into a vein or muscle. Amikacin is in the aminoglycoside family of medications. It works by blocking the function of the bacteria's 30S ribosomal subunit, making it unable to make protein.

Chemical Structure

Amikacin sulfate

CAS#39831-55-5 (sulfate)

Theoretical Analysis

MedKoo Cat#: 100955

Name: Amikacin sulfate

CAS#: 39831-55-5 (sulfate)

Chemical Formula: C22H47N5O21S2

Exact Mass: 0.0000

Molecular Weight: 781.75

Elemental Analysis: C, 33.80; H, 6.06; N, 8.96; O, 42.98; S, 8.20

Price and Availability

Size	Price	Availability
100mg	USD 90.00	Ready to Ship
1g	USD 150.00	Ready to ship
2g	USD 250.00	Ready to ship
5g	USD 450.00	Ready to ship
10g	USD 750.00	2 Weeks

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Related CAS #

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

Synonym

Amikacin sulfate; Amitrex; Antibiotic BB-K8 sulfate; BB-K8; Biklin; Biodacyn; Chemacin; Fabianol; Kaminax; Kancin-Gap; Likacin; Lukadin; BB K8; BBK8

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 bis(sulfate)

InChi Key

FXKSEJFHKVNEFI-GCZBSULCSA-N

InChi Code

InChI=1S/C22H43N5O13.2H2O4S/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;2*1-5(2,3)4/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36);2*(H2,1,2,3,4)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+;;/m0../s1

SMILES Code

NCC[C@@H](C(N[C@@H]1C[C@@H]([C@H]([C@@H]([C@H]1O[C@H]2O[C@@H]([C@H]([C@@H]([C@H]2O)N)O)CO)O)O[C@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)CN)N)=O)O.OS(=O)(O)=O.OS(=O)(O)=O

Appearance

White to off-white crystalline 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

Amikacin was patented in 1971 and came into commercial use in 1976. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is 13.80 to 130.50 USD for a month. In the United States a typical course of treatment costs 25 to 50 USD. It is made from kanamycin.

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#S8P09C28

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Amikacin disulfate is bactericidal, acting directly on the 30S and 50S bacerial ribosomal subunits to inhibit protein synthesis.

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
	DMSO	55.0	70.35

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 781.75 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: Smits A, Kulo A, van den Anker J, Allegaert K. The amikacin research program: a stepwise approach to validate dosing regimens in neonates. Expert Opin Drug Metab Toxicol. 2017 Feb;13(2):157-166. doi: 10.1080/17425255.2017.1234606. Epub 2016 Sep 21. Review. PubMed PMID: 27623706. 2: Waters V, Ratjen F. Inhaled liposomal amikacin. Expert Rev Respir Med. 2014 Aug;8(4):401-9. doi: 10.1586/17476348.2014.918507. Epub 2014 May 31. Review. PubMed PMID: 24882271. 3: Antoniu S, Azoicai D. Novel amikacin inhaled formulation for the treatment of lower respiratory tract infections. Drugs Today (Barc). 2013 Nov;49(11):683-92. doi: 10.1358/dot.2013.49.11.2033101. Review. PubMed PMID: 24308015. 4: Ehsan Z, Clancy JP. Management of Pseudomonas aeruginosa infection in cystic fibrosis patients using inhaled antibiotics with a focus on nebulized liposomal amikacin. Future Microbiol. 2015;10(12):1901-12. doi: 10.2217/fmb.15.117. Epub 2015 Nov 17. Review. PubMed PMID: 26573178; PubMed Central PMCID: PMC4944396. 5: Ehsan Z, Wetzel JD, Clancy JP. Nebulized liposomal amikacin for the treatment of Pseudomonas aeruginosa infection in cystic fibrosis patients. Expert Opin Investig Drugs. 2014 May;23(5):743-9. doi: 10.1517/13543784.2014.895322. Epub 2014 Mar 5. Review. PubMed PMID: 24597573. 6: Feng Y, Liu S, Wang Q, Wang L, Tang S, Wang J, Lu W. Rapid diagnosis of drug resistance to fluoroquinolones, amikacin, capreomycin, kanamycin and ethambutol using genotype MTBDRsl assay: a meta-analysis. PLoS One. 2013;8(2):e55292. doi: 10.1371/journal.pone.0055292. Epub 2013 Feb 1. Review. PubMed PMID: 23383320; PubMed Central PMCID: PMC3562191. 7: Zhanel GG, Lawson CD, Zelenitsky S, Findlay B, Schweizer F, Adam H, Walkty A, Rubinstein E, Gin AS, Hoban DJ, Lynch JP, Karlowsky JA. Comparison of the next-generation aminoglycoside plazomicin to gentamicin, tobramycin and amikacin. Expert Rev Anti Infect Ther. 2012 Apr;10(4):459-73. doi: 10.1586/eri.12.25. Review. PubMed PMID: 22512755. 8: Marsot A, Guilhaumou R, Riff C, Blin O. Amikacin in Critically Ill Patients: A Review of Population Pharmacokinetic Studies. Clin Pharmacokinet. 2017 Feb;56(2):127-138. doi: 10.1007/s40262-016-0428-x. Review. PubMed PMID: 27324191. 9: Georghiou SB, Magana M, Garfein RS, Catanzaro DG, Catanzaro A, Rodwell TC. Evaluation of genetic mutations associated with Mycobacterium tuberculosis resistance to amikacin, kanamycin and capreomycin: a systematic review. PLoS One. 2012;7(3):e33275. doi: 10.1371/journal.pone.0033275. Epub 2012 Mar 29. Review. PubMed PMID: 22479378; PubMed Central PMCID: PMC3315572. 10: Amikacin. Tuberculosis (Edinb). 2008 Mar;88(2):87-8. doi: 10.1016/S1472-9792(08)70003-9. Review. PubMed PMID: 18486037. 11: Jenkins A, Thomson AH, Brown NM, Semple Y, Sluman C, MacGowan A, Lovering AM, Wiffen PJ; (BSAC Working Party on Therapeutic Drug Monitoring).. Amikacin use and therapeutic drug monitoring in adults: do dose regimens and drug exposures affect either outcome or adverse events? A systematic review. J Antimicrob Chemother. 2016 Oct;71(10):2754-9. doi: 10.1093/jac/dkw250. Epub 2016 Jul 11. Review. PubMed PMID: 27494904. 12: Cunha BA. New uses for older antibiotics: nitrofurantoin, amikacin, colistin, polymyxin B, doxycycline, and minocycline revisited. Med Clin North Am. 2006 Nov;90(6):1089-107. Review. PubMed PMID: 17116438. 13: Young DC, Zobell JT, Stockmann C, Waters CD, Ampofo K, Sherwin CM, Spigarelli MG. Optimization of anti-pseudomonal antibiotics for cystic fibrosis pulmonary exacerbations: V. Aminoglycosides. Pediatr Pulmonol. 2013 Nov;48(11):1047-61. doi: 10.1002/ppul.22813. Epub 2013 Sep 2. Review. PubMed PMID: 24000183. 14: Falagas ME, Karageorgopoulos DE, Georgantzi GG, Sun C, Wang R, Rafailidis PI. Susceptibility of Gram-negative bacteria to isepamicin: a systematic review. Expert Rev Anti Infect Ther. 2012 Feb;10(2):207-18. doi: 10.1586/eri.11.170. Review. PubMed PMID: 22339194. 15: Garcia-Prats AJ, Schaaf HS, Hesseling AC. The safety and tolerability of the second-line injectable antituberculosis drugs in children. Expert Opin Drug Saf. 2016 Nov;15(11):1491-1500. Epub 2016 Aug 22. Review. PubMed PMID: 27548570. 16: Kuznetsova SM. [Amikacin--a semisynthetic aminoglycoside of the III generation]. Antibiot Khimioter. 2002;47(5):30-41. Review. Russian. PubMed PMID: 12365326. 17: van Ingen J, Kuijper EJ. Drug susceptibility testing of nontuberculous mycobacteria. Future Microbiol. 2014;9(9):1095-110. doi: 10.2217/fmb.14.60. Review. PubMed PMID: 25340838. 18: Rodieux F, Wilbaux M, van den Anker JN, Pfister M. Effect of Kidney Function on Drug Kinetics and Dosing in Neonates, Infants, and Children. Clin Pharmacokinet. 2015 Dec;54(12):1183-204. doi: 10.1007/s40262-015-0298-7. Review. PubMed PMID: 26138291; PubMed Central PMCID: PMC4661214. 19: Kent A, Turner MA, Sharland M, Heath PT. Aminoglycoside toxicity in neonates: something to worry about? Expert Rev Anti Infect Ther. 2014 Mar;12(3):319-31. doi: 10.1586/14787210.2014.878648. Epub 2014 Jan 21. Review. PubMed PMID: 24455994. 20: Wargo KA, Edwards JD. Aminoglycoside-induced nephrotoxicity. J Pharm Pract. 2014 Dec;27(6):573-7. doi: 10.1177/0897190014546836. Epub 2014 Sep 7. Review. PubMed PMID: 25199523.