2-{[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

• ChemBase ID: 677
• Molecular Formular: C21H43N5O7
• Molecular Mass: 477.59542
• Monoisotopic Mass: 477.31624874
• SMILES: O(C1C(O)C(OC2OC(CCC2N)C(NC)C)C(N)CC1N)C1OCC(O)(C(NC)C1O)C
• Canonical SMILES: CNC(C1CCC(C(O1)OC1C(N)CC(C(C1O)OC1OCC(C(C1O)NC)(C)O)N)N)C
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[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
• IUPAC Traditional name: refobacin; gentamicin
• Brand Name: Alcomicin; Apogen; Bristagen; G-Mycin; G-Myticin; Garamycin; Garamycin Otic Solution; Genoptic Liquifilm; Genoptic S.O.P.; Gentacidin; Gentafair; Gentak; Gentamar; Gentamcin Sulfate; Jenamicin; Ocu-Mycin; Spectro-Genta; U-gencin
• Synonyms: Gentamicin; O-2-Amino-2,3,4,6,7-pentadeoxy-6-(methylamino)-α-D-ribo-heptopyranosyl-(14)-O-[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(16)]-2-deoxy-D-streptamine Pentaacetate Salt; Gentamicin C1 Pentaacetate Salt

Database IDs

• CAS Number: 25876-10-2; 1403-66-3
• PubChem SID: 160964140; 46506523
• PubChem CID: 3467

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.549178
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -17.685123
• LogD (pH = 7.4): -11.792577
• Log P: -3.1371555
• Molar Refractivity: 118.0207 cm^3
• Polarizability: 49.566326 Å^3
• Polar Surface Area: 199.73 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -1.64
• LOG S: -1.58
• Solubility (Water): 1.26e+01 g/l

PROPERTIES

Physical Property

• Solubility: 100 mg/mL; Water
• Apperance: Off-White to Pale Green Solid
• Melting Point: 125-130°C
• Hydrophobicity(logP): -3.1

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

DrugBank - DB00798

• Drug Groups: approved
• Description: A complex of three different closely related aminoglycoside sulfates, Gentamicins C1, C2, and C1(subA), obtained from Micromonospora purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit protein synthesis (genetic translation). [PubChem]
• Indication: For treatment of serious infections caused by susceptible strains of the following microorganisms: P. aeruginosa, Proteus species (indole-positive and indole-negative), E. coli, Klebsiella-Enterobactor-Serratia species, Citrobacter species and Staphylococcus species (coagulase-positive and coagulase-negative).
• Pharmacology: Gentamicin is a broad spectrum aminoglycoside antibiotic. Aminoglycosides work by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA, leaving the bacterium unable to synthesize proteins vital to its growth. Aminoglycosides are useful primarily in infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. In addition, some mycobacteria, including the bacteria that cause tuberculosis, are susceptible to aminoglycosides. Infections caused by Gram-positive bacteria can also be treated with aminoglycosides, but other types of antibiotics are more potent and less damaging to the host. In the past the aminoglycosides have been used in conjunction with penicillin-related antibiotics in streptococcal infections for their synergistic effects, particularly in endocarditis. Aminoglycosides are mostly ineffective against anaerobic bacteria, fungi and viruses.
• Toxicity: Mild and reversible nephrotoxicity may be observed in 5 - 25% of patients. Gentamicin accumulates in proximal renal tubular cells and causes cell damage. Tubular cell regeneration occurs despite continued drug exposure. Toxicity usually occurs several days following initiation of therapy. May cause irreversible ototoxicity. Otoxocity appears to be correlated to cumulative lifetime exposure. Drug accumulation in the endolymph and perilymph of the inner ear causes irreversible damage to hair cells of the cochlea or summit of ampullar cristae in the vestibular complex. High frequency hearing is lost first with progression leading to loss of low frequency hearing. Further toxicity may lead to retrograde degeneration of the 8th cranial (vestibulocochlear) nerve. Vestibular toxicity may cause vertigo, nausea, vomiting, dizziness and loss of balance.; Mouse, intravenous LD50: 52 mg/kg; rat, intravenous LD50: 96 mg/kg.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Injections lead to peak serum concentrations in 30-60 minutes. Topical gentamicin is readily absorbed from large burned, denuded, or granulating areas but not through intact skin. Absorption of gentamicin is faster and greater with the cream compared to the ointment. Gentamicin is absorbed in small quantities following topical application to the eye. Gentamicin is also absorbed in small amounts following topical application to the ear (especially if the eardrum is perforated or if tissue damage is present). Gentamicin is very poorly absorbed orally.
• Half Life: 3-3½ hours in infants one week to six months of age; this increases to 5½ hours in full-term and large premature infants less than one week old.
• Protein Binding: Low (between 0 and 30%)
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - G360585

Antibacterial.

REFERENCES

• Holt, H.A., et al.: J. Antimicrob. Chemother., 34, 747 (1994)
• Wilschanski, M., et al.: Am. J. Respir. Crit. Care Med., 161, 860 (1994)