Gentamicin sulfate | CAS#1405-41-0 | Aminoglycoside antibiotic

MedKoo Cat#: 329895 | Name: Gentamicin sulfate

Description:

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

Gentamicin is an antibiotic used to treat several types of bacterial infections. This may include bone infections, endocarditis, pelvic inflammatory disease, meningitis, pneumonia, urinary tract infections, and sepsis among others. It is not effective for gonorrhea or chlamydia infections. Gentamicin is a complex of three different closely related aminoglycoside sulfates, Gentamicins C1, C2, and C1(subA), obtained from Micromonospora purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit protein synthesis.

Chemical Structure

Gentamicin sulfate

CAS#1405-41-0 (sulfate)

Theoretical Analysis

MedKoo Cat#: 329895

Name: Gentamicin sulfate

CAS#: 1405-41-0 (sulfate)

Chemical Formula: C21H43N5O7.H2SO4

Exact Mass: 0.0000

Molecular Weight: 575.66

Elemental Analysis:

Price and Availability

Size	Price	Availability
500mg	USD 150.00	Ready to ship
1g	USD 250.00	Ready to ship
2g	USD 400.00	Ready to ship
5g	USD 750.00	Ready to ship

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Related CAS #

1405-41-0 (sulfate) 1403-66-3 (free base)

Synonym

Gentamicin sulfate; NSC-82261; Refobacin; Sch 9724; U-Gencin; Gentacidin; Gentafair; Gentak;Apogen; Bristagen; Garacin; Garamycin;

IUPAC/Chemical Name

mixtures of three isomers (Gentamicins C1, C2, and C1(subA).

InChi Key

RDEIXVOBVLKYNT-UHFFFAOYSA-N

InChi Code

SMILES Code

[R][C@H](O1)CC[C@@H](N)[C@H]1O[C@@H]([C@H](N)C[C@@H]2N)[C@@H](O)[C@H]2O[C@@H]3[C@H](O)[C@H](NC)[C@@](O)(CO3)C.C[C@@H]([R])NC.C[C@H]([R])N.NC[R].O=S(O)(O)=O

Appearance

Solid powder

Purity

80% (total nitrogen: 8.0 to 10.0 %)

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

It can be given intravenously, by injection into a muscle, or topically. Topical formulations may be used in burns or for infections of the outside of the eye. In the developed world it is often only used for two days until bacterial cultures determine what antibiotics the infection is sensitive to. The dose required should be monitored by blood testing.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Gentamicin sulfate inhibits DNase I with an IC50 of 0.57 mM.

In vitro activity:

Gentamicin has potential in the reduction of gastric cancer cell growth. Gentamicin-treated cells exhibited large size, suggesting that gentamicin induced a change of cell morphology. Gentamicin treatment caused a reduction of cell labeling, confirming a significant inhibition of cell growth. Images showed a strong reduction of labeling in the gentamicin-treated cells. In accordance, the growth arrest and DNA-damage 45A gene was strongly upregulated. Reference: Int J Mol Sci. 2019 Sep 6;20(18):4375. https://pubmed.ncbi.nlm.nih.gov/31489901/

In vivo activity:

Quantitative real-time PCR revealed significantly increased expression of fibrogenic genes a-SMA, FN, and Col1, as well as of several proinflammatory markers (TNF-α, IL-6, and IL-1β), in gentamicin-treated mouse kidneys. These results demonstrate that gentamicin induces significant renal inflammation and interstitial fibrosis in mice. Reference: J Am Soc Nephrol. 2020 Sep;31(9):2097-2115. https://pubmed.ncbi.nlm.nih.gov/32641397/

	Solvent	mg/mL	mM
Solubility
	DMSO	30.0	52.11

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 575.66 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. Sun Y, He Z, Li J, Gong S, Yuan S, Li T, Ning N, Xing L, Zhang L, Chen F, Li Z, Wang J, Luo D, Wang H. Gentamicin Induced Microbiome Adaptations Associate With Increased BCAA Levels and Enhance Severity of Influenza Infection. Front Immunol. 2021 Feb 23;11:608895. doi: 10.3389/fimmu.2020.608895. PMID: 33708192; PMCID: PMC7940682. 2. Albi E, Cataldi S, Ceccarini MR, Conte C, Ferri I, Fettucciari K, Patria FF, Beccari T, Codini M. Gentamicin Targets Acid Sphingomyelinase in Cancer: The Case of the Human Gastric Cancer NCI-N87 Cells. Int J Mol Sci. 2019 Sep 6;20(18):4375. doi: 10.3390/ijms20184375. PMID: 31489901; PMCID: PMC6770866. 3. Huang H, Jin WW, Huang M, Ji H, Capen DE, Xia Y, Yuan J, Păunescu TG, Lu HAJ. Gentamicin-Induced Acute Kidney Injury in an Animal Model Involves Programmed Necrosis of the Collecting Duct. J Am Soc Nephrol. 2020 Sep;31(9):2097-2115. doi: 10.1681/ASN.2019020204. Epub 2020 Jul 8. PMID: 32641397; PMCID: PMC7461673. 4. O'Reilly M, Young L, Kirkwood NK, Richardson GP, Kros CJ, Moore AL. Gentamicin Affects the Bioenergetics of Isolated Mitochondria and Collapses the Mitochondrial Membrane Potential in Cochlear Sensory Hair Cells. Front Cell Neurosci. 2019 Sep 13;13:416. doi: 10.3389/fncel.2019.00416. PMID: 31572129; PMCID: PMC6753894.

In vitro protocol:

In vivo protocol:

1. Huang H, Jin WW, Huang M, Ji H, Capen DE, Xia Y, Yuan J, Păunescu TG, Lu HAJ. Gentamicin-Induced Acute Kidney Injury in an Animal Model Involves Programmed Necrosis of the Collecting Duct. J Am Soc Nephrol. 2020 Sep;31(9):2097-2115. doi: 10.1681/ASN.2019020204. Epub 2020 Jul 8. PMID: 32641397; PMCID: PMC7461673. 2. O'Reilly M, Young L, Kirkwood NK, Richardson GP, Kros CJ, Moore AL. Gentamicin Affects the Bioenergetics of Isolated Mitochondria and Collapses the Mitochondrial Membrane Potential in Cochlear Sensory Hair Cells. Front Cell Neurosci. 2019 Sep 13;13:416. doi: 10.3389/fncel.2019.00416. PMID: 31572129; PMCID: PMC6753894.

1: Hayward RS, Harding J, Molloy R, Land L, Longcroft-Neal K, Moore D, Ross JDC. Adverse effects of a single dose of gentamicin in adults: a systematic review. Br J Clin Pharmacol. 2017 Sep 21. doi: 10.1111/bcp.13439. [Epub ahead of print] Review. PubMed PMID: 28940715. 2: Dean L. Gentamicin Therapy and MT-RNR1 Genotype. 2015 Apr 29. In: Pratt V, McLeod H, Dean L, Malheiro A, Rubinstein W, editors. Medical Genetics Summaries [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2012-. Available from http://www.ncbi.nlm.nih.gov/books/NBK285956/ PubMed PMID: 28520359. 3: Randjelovic P, Veljkovic S, Stojiljkovic N, Sokolovic D, Ilic I. Gentamicin nephrotoxicity in animals: Current knowledge and future perspectives. EXCLI J. 2017 Mar 24;16:388-399. doi: 10.17179/excli2017-165. eCollection 2017. Review. PubMed PMID: 28507482; PubMed Central PMCID: PMC5427480. 4: Tsai CC, Yang PS, Liu CL, Wu CJ, Hsu YC, Cheng SP. Comparison of topical mupirocin and gentamicin in the prevention of peritoneal dialysis-related infections: A systematic review and meta-analysis. Am J Surg. 2018 Jan;215(1):179-185. doi: 10.1016/j.amjsurg.2017.03.005. Epub 2017 Mar 15. Review. PubMed PMID: 28341139. 5: Llanos-Paez CC, Hennig S, Staatz CE. Population pharmacokinetic modelling, Monte Carlo simulation and semi-mechanistic pharmacodynamic modelling as tools to personalize gentamicin therapy. J Antimicrob Chemother. 2017 Mar 1;72(3):639-667. doi: 10.1093/jac/dkw461. Review. PubMed PMID: 28062683. 6: Rao SC, Srinivasjois R, Moon K. One dose per day compared to multiple doses per day of gentamicin for treatment of suspected or proven sepsis in neonates. Cochrane Database Syst Rev. 2016 Dec 6;12:CD005091. doi: 10.1002/14651858.CD005091.pub4. Review. PubMed PMID: 27921299. 7: Jaiswal N, Singh M, Kondel R, Kaur N, Thumburu KK, Kumar A, Kaur H, Chadha N, Gupta N, Agarwal A, Malhotra S, Shafiq N. Feasibility and efficacy of gentamicin for treating neonatal sepsis in community-based settings: a systematic review. World J Pediatr. 2016 Nov;12(4):408-414. Epub 2016 Feb 1. Review. PubMed PMID: 26830306. 8: Konstantelias AA, Polyzos KA, Falagas ME. Gentamicin-Collagen Sponges for the Prevention of Surgical Site Infections: A Meta-Analysis of Randomized Controlled Trials. Surg Infect (Larchmt). 2016 Oct;17(5):601-9. doi: 10.1089/sur.2016.025. Epub 2016 Jul 21. Review. PubMed PMID: 27441956. 9: Rapetto F, Bruno VD, Guida G, Marsico R, Chivasso P, Zebele C. Gentamicin-Impregnated Collagen Sponge: Effectiveness in Preventing Sternal Wound Infection in High-Risk Cardiac Surgery. Drug Target Insights. 2016 May 29;10(Suppl 1):9-13. doi: 10.4137/DTI.S39077. eCollection 2016. Review. PubMed PMID: 27279734; PubMed Central PMCID: PMC4886695. 10: Byrnes M, Dorman R. Use of Gentamicin as Empiric Coverage for Ventilator-Associated Pneumonia: The "Con" Perspective. Surg Infect (Larchmt). 2016 Jun;17(3):334-6. doi: 10.1089/sur.2015.278. Review. PubMed PMID: 27206240. 11: Witkowski J, Wnukiewicz W, Reichert P. Polymers as Carriers of Gentamicin in Traumatology and Orthopedic Surgery - Current State Of Knowledge. Polim Med. 2016 Jan-Jun;46(1):101-104. doi: 10.17219/pim/65053. Review. PubMed PMID: 28397425. 12: Jian X, Deng Z, Sun Y. [Aminoglycoside gentamicin research: fundamental progress and new application prospects]. Sheng Wu Gong Cheng Xue Bao. 2015 Jun;31(6):829-44. Review. Chinese. PubMed PMID: 26672360. 13: Lv YF, Wang J, Dong F, Yang DH. Meta-analysis of local gentamicin for prophylaxis of surgical site infections in colorectal surgery. Int J Colorectal Dis. 2016 Feb;31(2):393-402. doi: 10.1007/s00384-015-2454-9. Epub 2015 Nov 27. Review. PubMed PMID: 26614505. 14: Nguyen AL, Pronk AA, Furnée EJ, Pronk A, Davids PH, Smakman N. Local administration of gentamicin collagen sponge in surgical excision of sacrococcygeal pilonidal sinus disease: a systematic review and meta-analysis of the literature. Tech Coloproctol. 2016 Feb;20(2):91-100. doi: 10.1007/s10151-015-1381-7. Epub 2015 Nov 6. Review. PubMed PMID: 26546004. 15: Metsemakers WJ, Reul M, Nijs S. The use of gentamicin-coated nails in complex open tibia fracture and revision cases: A retrospective analysis of a single centre case series and review of the literature. Injury. 2015 Dec;46(12):2433-7. doi: 10.1016/j.injury.2015.09.028. Epub 2015 Oct 8. Review. PubMed PMID: 26477343. 16: Musiime GM, Seale AC, Moxon SG, Lawn JE. Risk of gentamicin toxicity in neonates treated for possible severe bacterial infection in low- and middle-income countries: Systematic Review. Trop Med Int Health. 2015 Dec;20(12):1593-606. doi: 10.1111/tmi.12608. Epub 2015 Oct 23. Review. PubMed PMID: 26426298. 17: Musters GD, Burger JW, Buskens CJ, Bemelman WA, Tanis PJ. Local Application of Gentamicin in the Prophylaxis of Perineal Wound Infection After Abdominoperineal Resection: A Systematic Review. World J Surg. 2015 Nov;39(11):2786-94. doi: 10.1007/s00268-015-3159-5. Review. PubMed PMID: 26170157; PubMed Central PMCID: PMC4591195. 18: Kowalewski M, Pawliszak W, Zaborowska K, Navarese EP, Szwed KA, Kowalkowska ME, Kowalewski J, Borkowska A, Anisimowicz L. Gentamicin-collagen sponge reduces the risk of sternal wound infections after heart surgery: Meta-analysis. J Thorac Cardiovasc Surg. 2015 Jun;149(6):1631-40.e1-6. doi: 10.1016/j.jtcvs.2015.01.034. Epub 2015 Jan 23. Review. PubMed PMID: 25703409. 19: Hathorn E, Dhasmana D, Duley L, Ross JD. The effectiveness of gentamicin in the treatment of Neisseria gonorrhoeae: a systematic review. Syst Rev. 2014 Sep 19;3:104. doi: 10.1186/2046-4053-3-104. Review. PubMed PMID: 25239090; PubMed Central PMCID: PMC4188483. 20: Mishra PK, Ashoub A, Salhiyyah K, Aktuerk D, Ohri S, Raja SG, Luckraz H. Role of topical application of gentamicin containing collagen implants in cardiac surgery. J Cardiothorac Surg. 2014 Jul 8;9:122. doi: 10.1186/1749-8090-9-122. Review. PubMed PMID: 25005533; PubMed Central PMCID: PMC4227288.