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Gentamicin

CAT: 0804-HY-A0276A-05Size: 100 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-A0276A-05Size:100 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Gentamicin, an orally active aminoglycoside antibiotic, inhibits the growth of both gram-positive and gram-negative bacteria and to inhibit several strains of mycoplasma in tissue culture. Gentamicin inhibits DNase I with an IC50 of 0.57 mM[1][2][3][4].
CAS Number
1403-66-3
UNSPSC
12352005
Hazard Statement
H317, H334
Target
Antibiotic; Bacterial
Type
Reference compound
Related Pathways
Anti-infection
Applications
COVID-19-anti-virus
Field of Research
Infection; Cancer
Assay Protocol
https://www.medchemexpress.com/gentamicin.html
Solubility
H2O : 175 mg/mL (ultrasonic)
Smiles
O[C@]1(C)C(NC)[C@@H](O)[C@@H](O[C@H]2C(N)C[C@H](N)[C@@H](O[C@@H]3[C@H](N)CC[C@@H]([R])O3)[C@@H]2O)OC1.NC[*].C[C@H]([*])N.C[C@H]([*])NC.[R=].[or].[or]
Molecular Formula
C (19-21) H (39-43) N5O7
Precautions
H317, H334
References & Citations
[1]Xu W, et al. A rapid and sensitive method for kinetic study and activity assay of DNase I in vitro based on a GO-quenched hairpin probe. Anal Bioanal Chem. 2016 May;408 (14) :3801-9.|[2]Rudin A, et al. Antibacterial activity of gentamicin sulfate in tissue culture. Appl Microbiol. 1970 Dec;20 (6) :989-90.|[3]Kumar CG, et al. Microbial biosynthesis and applications of gentamicin: a critical appraisal. Crit Rev Biotechnol. 2008;28 (3) :173-212.|[4]Espersen F, et al. Effect of treatment with methicillin and gentamicin in a new experimental mouse model of foreignbody infection. Antimicrob Agents Chemother. 1994 Sep;38 (9) :2047-53.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light, stored under nitrogen)
Scientific Category
Reference compound1
Clinical Information
Launched
Isoform
Aminoglycoside
Citation 01
AMB Express. 2024 Dec 24;14 (1) :141.|Bio Protoc. 2025 Feb 20;15 (4) :e5221.|Biochem Pharmacol. 2025 Sep 17;242:117343.|Biomed Pharmacother. 2023 Dec 31:169:115856.|bioRxiv. 2024 May 10.|BMC Microbiol. 2025 Apr 29;25 (1) :257.|Cancer Res. 2025 Oct 9.|Cell. 2024 Feb 15;187 (4) :882-896.e17|Chin J Traumatol. 2024 Jul 3:S1008-1275 (24) 00075-0.|Curr Microbiol. 2023 May 31;80 (7) :230.|Curr Microbiol. 2025 Aug 16;82 (10) :456.|Curr Res Food Sci. 2025 May 16:10:101084.|Cytotherapy. 2025 Sep 13.|Emerg Microbes Infect. 2024 Dec;13 (1) :2321981.|Exp Eye Res. 2025 Oct 16:262:110698.|Food Chem. 2023 Mar 1:403:134399.|Food Funct. 2025 Feb 3;16 (3) :1041-1059.|Future Microbiol. 2025 Oct 13:1-10.|Infect Genet Evol. 2025 Sep:133:105780.|Int Immunopharmacol. 2025 May 21:159:114888.|Int J Biol Macromol. 2025 May;305 (Pt 2) :141278.|Int J Infect Dis. 2026 Jan:162:108165.|Int J Med Microbiol. 2023 Mar 28;313 (2) :151578.|MedComm (2020) . 2025 Jan 8;6 (1) :e70046.|Microbiol Spectr. 2025 Aug 29:e0059025.|Microbiol Spectr. 2025 May 19:e0307424.|Microbiol Spectr. 2025 Oct 16:e0160325.|Microorganisms. 2024 Mar 13;12 (3) :575.|Microorganisms. 2025 Apr 18;13 (4) :938.|Nat Microbiol. 2023 Mar;8 (3) :410-423.|Naunyn Schmiedebergs Arch Pharmacol. 2025 Apr;398 (4) :3681-3695.|Patent. US20240319170A1|Pathogens. 2024 Nov 15;13 (11) :1003.|Physiol Res. 2025 Mar 24;74 (1) :79-92. |Transl Lung Cancer Res. 2025 Jun 30;14 (6) :2159-2179.|Vet Microbiol. 2024 May:292:110046.|Vet Res Commun. 2024 Dec;48 (6) :3859-3872.|Virulence. 2024 Dec;15 (1) :2415952.|World J Gastroenterol. 2025 Jul 28;31 (28) :107361.|ACS Appl Mater Interfaces. 2019 Oct 16;11 (41) :38190-38204. |ACS Infect Dis. 2024 Apr 12;10 (4) :1327-1338.|Am J Physiol Cell Physiol. 2019 Aug 1;317 (2) :C277-C286.|Appl Microbiol Biotechnol. 2022 Apr;106 (7) :2689-2702.|Aquaculture. 2021, 736248.|Autophagy. 2025 Jul 27:1-23.|Cancer Cell. 2025 Jul 29:S1535-6108 (25) 00318-6.|Cell Death Dis. 2023 Jan 11;14 (1) :15.|Cell Host Microbe. 2024 Jul 23:S1931-3128 (24) 00254-3.|Cell Transplant. 2021 Jan-Dec:30:963689721997151.|Evid Based Complement Alternat Med. 2015:2015:639412.|Immun Inflamm Dis. 2024 Jul;12 (7) :e1149.|Int J Biol Sci. 2024 Oct 7;20 (14) :5415-5435.|J Ethnopharmacol. 2020 Sep 15;259:112882. |Mol Immunol. 2017 Dec:92:151-160.|Mol Med Rep. 2016 Dec;14 (6) :5304-5310.|Mutat Res Genet Toxicol Environ Mutagen. 2023 May-Jun:888:503636.|Nat Aging. 2025 May;5 (5) :848-867.|Nat Commun. 2022 Mar 2;13 (1) :1116.|Research Square Print. October 6th, 2022.|Toxicology. 2023 Jan 1:483:153386.

Chemical Information

Gentamicin

Gentamicin is a bactericidal aminoglycoside that was discovered and isolated from Micromonospora purpurea in 1963. It is one of the most frequently prescribed aminoglycosides due to its spectrum of activity, low cost, and availability. Gentamicin is effective against both gram-positive and gram-negative organisms but is particularly useful for the treatment of severe gram-negative infections including those caused by Pseudomonas aeruginosa. There is the added benefit of synergy when gentamicin is co-administered with other antibacterials such as beta-lactams. This synergistic activity is not only important for the treatment of complex infections, but can also contribute to dose optimization and reduced adverse effects. Although gentamicin is well-established and may be used in a variety of clinical applications, it is also associated with severe adverse effects including nephrotoxicity and ototoxicity which may limit its use.

CAS Number1403-66-3
PubChem CID3467
IUPAC Name2-[4,6-diamino-3-[3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol
Molecular FormulaC21H43N5O7
Molecular Weight477.6
XLogP-4.1
Topological Polar Surface Area200
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count12
Rotatable Bond Count7
Heavy Atom Count33
Formal Charge0
Complexity636
SMILES
CC(C1CCC(C(O1)OC2C(CC(C(C2O)OC3C(C(C(CO3)(C)O)NC)O)N)N)N)NC
InChI
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
InChIKey
CEAZRRDELHUEMR-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Gentamicin
CAS: 1403-66-3
CID: 3467
Formula: C21H43N5O7
MW: 477.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight477.6
XLogP3-4.1
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count12
Rotatable Bond Count7
Exact Mass477.31624873
Monoisotopic Mass477.31624873
Topological Polar Surface Area200 Ų
Heavy Atom Count33
Formal Charge0
Complexity636
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count13
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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