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Gentamicin

CAT: 0931-T25447-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0931-T25447-01Size:5 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
1403-66-3
Target
Antibiotic, Antibacterial
Related Pathways
Microbiology/Virology
Bioactivity
Gentamicin (Centicin) is a broad-spectrum aminoglycoside antibiotic with antibacterial activity, inhibiting the growth of Gram-positive and Gram-negative bacteria, and can be used to study ocular infections.
Smiles
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Molecular Formula
C21H43N5O7
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

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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