Gentamicin | CAS#1403-66-3 | antibiotic

MedKoo Cat#: 461198 | Name: Gentamicin

Description:

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

Gentamicin is a widely used antibiotic in the intensive care unit (ICU).

Chemical Structure

Gentamicin

CAS#1403-66-3 (free base)

Theoretical Analysis

MedKoo Cat#: 461198

Name: Gentamicin

CAS#: 1403-66-3 (free base)

Chemical Formula: C21H43N5O7

Exact Mass: 477.3162

Molecular Weight: 477.60

Elemental Analysis: C, 52.81; H, 9.08; N, 14.66; O, 23.45

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

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

Synonym

Gentamicin; Centicin; Lyramycin; Oksitselanim; Refobacin; Septigen; Uromycine;

IUPAC/Chemical Name

(2R,3R,4S,5R)-2-(((1S,2R,3S,4S,6S)-4,6-diamino-3-(((2S,3S,6S)-3-amino-6-((S)-1-(methylamino)ethyl)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-5-methyl-4-(methylamino)tetrahydro-2H-pyran-3,5-diol

InChi Key

CEAZRRDELHUEMR-ZMRLYRBASA-N

InChi Code

InChI=1S/C21H43N5O7/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20/h9-20,25-29H,5-8,22-24H2,1-4H3/t9-,10-,11-,12-,13-,14+,15+,16-,17-,18-,19-,20+,21-/m0/s1

SMILES Code

N[C@H]1CC[C@@H]([C@H](C)NC)O[C@H]1O[C@@H]([C@H](C[C@@H]2N)N)[C@@H](O)[C@H]2O[C@@H]3[C@H](O)[C@H](NC)[C@@](O)(CO3)C

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

>3 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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 477.60 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

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The impact of frailty on pharmacokinetics in older people: using gentamicin population pharmacokinetic modeling to investigate changes in renal drug clearance by glomerular filtration. Eur J Clin Pharmacol. 2014 May;70(5):549-55. doi: 10.1007/s00228-014-1652-7. Epub 2014 Feb 14. PubMed PMID: 24522409. 5: Telechea H, Gesuele J, Grosso P, Galarraga F, Guzzo F, Speranza N, Antúnez F, Nanni L, Giachetto G. [Gentamicin pharmacokinetics in term newborn: ¿Is it necessary to systematically monitor plasmatic levels?]. Rev Chilena Infectol. 2016 Feb;33(1):7-11. doi: 10.4067/S0716-10182016000100001. Spanish. PubMed PMID: 26965871. 6: Imbuluzqueta E, Gamazo C, Lana H, Campanero MÁ, Salas D, Gil AG, Elizondo E, Ventosa N, Veciana J, Blanco-Prieto MJ. Hydrophobic gentamicin-loaded nanoparticles are effective against Brucella melitensis infection in mice. Antimicrob Agents Chemother. 2013 Jul;57(7):3326-33. doi: 10.1128/AAC.00378-13. Epub 2013 May 6. PubMed PMID: 23650167; PubMed Central PMCID: PMC3697350. 7: Veinstein A, Venisse N, Badin J, Pinsard M, Robert R, Dupuis A. Gentamicin in hemodialyzed critical care patients: early dialysis after administration of a high dose should be considered. Antimicrob Agents Chemother. 2013 Feb;57(2):977-82. doi: 10.1128/AAC.01762-12. Epub 2012 Dec 10. PubMed PMID: 23229487; PubMed Central PMCID: PMC3553715. 8: Webb JC, Gbejuade H, Lovering A, Spencer R. Characterisation of in vivo release of gentamicin from polymethyl methacrylate cement using a novel method. Int Orthop. 2013 Oct;37(10):2031-6. doi: 10.1007/s00264-013-1914-5. Epub 2013 May 19. PubMed PMID: 23685878; PubMed Central PMCID: PMC3779555. 9: Rankin AJ, Lanuza R, KuKanich B, Crumley WC, Pucket JD, Allbaugh RA, Meekins JM. Measurement of plasma gentamicin concentrations postchemical ciliary body ablation in dogs with chronic glaucoma. Vet Ophthalmol. 2016 Jan;19(1):57-62. doi: 10.1111/vop.12258. Epub 2015 Feb 17. PubMed PMID: 25688853. 10: Salouti M, Heidari Z, Ahangari A, Zare S. Enhanced delivery of gentamicin to infection foci due to Staphylococcus aureus using gold nanorods. Drug Deliv. 2016;23(1):49-54. doi: 10.3109/10717544.2014.903533. Epub 2014 Apr 24. PubMed PMID: 24758188. 11: 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. 12: Ravis WR, Llanos-Cuentas A, Sosa N, Kreishman-Deitrick M, Kopydlowski KM, Nielsen C, Smith KS, Smith PL, Ransom JH, Lin YJ, Grogl M. Pharmacokinetics and absorption of paromomycin and gentamicin from topical creams used to treat cutaneous leishmaniasis. Antimicrob Agents Chemother. 2013 Oct;57(10):4809-15. doi: 10.1128/AAC.00628-13. Epub 2013 Jul 22. PubMed PMID: 23877689; PubMed Central PMCID: PMC3811440. 13: Dhuria RS, Bhatti R, Bhatti MS, Singh P, Whitcomb PJ, Thukral AK. Experimental design optimization for electrochemical removal of gentamicin: toxicity evaluation and degradation pathway. Water Sci Technol. 2013;67(9):2017-24. doi: 10.2166/wst.2013.076. PubMed PMID: 23656945. 14: Varghese JM, Roberts JA, Wallis SC, Boots RJ, Healy H, Fassett RG, Lipman J, Ranganathan D. Pharmacokinetics of intraperitoneal gentamicin in peritoneal dialysis patients with peritonitis (GIPD study). Clin J Am Soc Nephrol. 2012 Aug;7(8):1249-56. doi: 10.2215/CJN.12211211. Epub 2012 Jun 14. PubMed PMID: 22700884; PubMed Central PMCID: PMC3408127. 15: Dersch-Mills D, Akierman A, Alshaikh B, Yusuf K. Validation of a dosage individualization table for extended-interval gentamicin in neonates. Ann Pharmacother. 2012 Jul-Aug;46(7-8):935-42. doi: 10.1345/aph.1R029. Epub 2012 Jun 26. PubMed PMID: 22739714. 16: Alshaikh B, Dersch-Mills D, Taylor R, Akierman AR, Yusuf K. Extended interval dosing of gentamicin in premature neonates ≤ 28-week gestation. Acta Paediatr. 2012 Nov;101(11):1134-9. doi: 10.1111/j.1651-2227.2012.02820.x. Epub 2012 Sep 7. PubMed PMID: 22897142. 17: Rotov KA, Tikhonov SN, Alekseev VV, Snatenkov EA. Pharmacokinetics of liposomal gentamicin. Bull Exp Biol Med. 2012 Aug;153(4):475-7. English, Russian. PubMed PMID: 22977848. 18: Fullas F, Padomek MT, Thieman CJ, Van Gorp AE. Comparative evaluation of six extended-interval gentamicin dosing regimens in premature and full-term neonates. Am J Health Syst Pharm. 2011 Jan 1;68(1):52-6. doi: 10.2146/ajhp100114. PubMed PMID: 21164066. 19: Momoh MA, Esimone CO. Phospholipon 90H (P90H)-based PEGylated microscopic lipospheres delivery system for gentamicin: an antibiotic evaluation. Asian Pac J Trop Biomed. 2012 Nov;2(11):889-94. doi: 10.1016/S2221-1691(12)60248-2. PubMed PMID: 23569866; PubMed Central PMCID: PMC3609242. 20: Barth RE, Vogely HC, Hoepelman AI, Peters EJ. 'To bead or not to bead?' Treatment of osteomyelitis and prosthetic joint-associated infections with gentamicin bead chains. Int J Antimicrob Agents. 2011 Nov;38(5):371-5. doi: 10.1016/j.ijantimicag.2011.03.008. Epub 2011 May 6. Review. PubMed PMID: 21549570.