Gentamicin sulfateProduct ingredient for Gentamicin

Name

Gentamicin sulfate

Drug Entry

Gentamicin

Gentamicin is a bactericidal aminoglycoside that was discovered and isolated from Micromonospora purpurea in 1963.⁷ It is one of the most frequently prescribed aminoglycosides due to its spectrum of activity, low cost, and availability.^5,8 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.^6,10,11 There is the added benefit of synergy when gentamicin is co-administered with other antibacterials such as beta-lactams.¹¹ This synergistic activity is not only important for the treatment of complex infections, but can also contribute to dose optimization and reduced adverse effects.^10,11

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.¹²

See full entry for Gentamicin

Accession Number

DBSALT000690

Structure

Similar Structures

Synonyms

Gentamicin (as sulfate) / Gentamicin (as sulphate) / Gentamicin (gentamycin sulfate) / Gentamicin C complex sulfate / Gentamicin sulfate (salt) / Gentamicin sulphate

External IDs

NSC-82261 / SCH 9724 / SCH-9724

UNII

8X7386QRLV

CAS Number

1405-41-0

Weight

Average: 1488.8
Monoisotopic: 1487.869175759

Chemical Formula

C₆₀H₁₂₅N₁₅O₂₅S

InChI Key

RDEIXVOBVLKYNT-VQBXQJRRSA-N

InChI

InChI=1S/C21H43N5O7.C20H41N5O7.C19H39N5O7.H2O4S/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;1-8(21)12-5-4-9(22)18(30-12)31-15-10(23)6-11(24)16(13(15)26)32-19-14(27)17(25-3)20(2,28)7-29-19;1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17;1-5(2,3)4/h9-20,25-29H,5-8,22-24H2,1-4H3;8-19,25-28H,4-7,21-24H2,1-3H3;8-18,24-27H,3-7,20-23H2,1-2H3;(H2,1,2,3,4)/t9?,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+;8?,9-,10+,11-,12+,13+,14-,15-,16+,17-,18-,19-,20+;8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19-;/m110./s1

IUPAC Name

(2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; (2R,3R,4R,5R)-2-{[(1S,2S,3R,4S,6R)-4,6-diamino-3-{[(2R,3R,6S)-3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol; sulfuric acid

SMILES

OS(O)(=O)=O.[H][C@@]1(CN)CC[C@@H](N)[C@@H](O[C@]2([H])[C@@H](N)C[C@@H](N)[C@H](O[C@@]3([H])OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1.[H][C@]1(CC[C@@H](N)[C@@H](O[C@]2([H])[C@@H](N)C[C@@H](N)[C@H](O[C@@]3([H])OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1)C(C)N.[H][C@]1(CC[C@@H](N)[C@@H](O[C@]2([H])[C@@H](N)C[C@@H](N)[C@H](O[C@@]3([H])OC[C@](C)(O)[C@H](NC)[C@H]3O)[C@H]2O)O1)C(C)NC

External Links

PubChem Compound: 3467
ChemSpider: 8031050
ChEMBL: CHEMBL3039594
Wikipedia: Gentamicin

Predicted Properties

Property	Value	Source
Water Solubility	12.6 mg/mL	ALOGPS
logP	-1.6	ALOGPS
logP	-3.1	Chemaxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	12.55	Chemaxon
pKa (Strongest Basic)	10.12	Chemaxon
Physiological Charge	5	Chemaxon
Hydrogen Acceptor Count	12	Chemaxon
Hydrogen Donor Count	8	Chemaxon
Polar Surface Area	199.73 Å²	Chemaxon
Rotatable Bond Count	19	Chemaxon
Refractivity	118.02 m³·mol^-1	Chemaxon
Polarizability	51.52 Å³	Chemaxon
Number of Rings	9	Chemaxon
Bioavailability	0	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Gentamicin sulfateProduct ingredient for Gentamicin

Structure for Gentamicin sulfate (DBSALT000690)