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
- Accession Number
- DBSALT000690
- Structure
- 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