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1403-66-3 molecular structure
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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 and InChIs

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

Cite this record

CBID:677 http://www.chembase.cn/molecule-677.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
1403-66-3
25876-10-2
PubChem SID
46506523
160964140
PubChem CID
3467

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
G360585 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 12.549178  H Acceptors 12 
H Donor LogD (pH = 5.5) -17.685123 
LogD (pH = 7.4) -11.792577  Log P -3.1371555 
Molar Refractivity 118.0207 cm3 Polarizability 49.566326 Å3
Polar Surface Area 199.73 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P -1.64  LOG S -1.58 
Solubility (Water) 1.26e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
100 mg/mL expand Show data source
Water expand Show data source
Apperance
Off-White to Pale Green Solid expand Show data source
Melting Point
125-130°C expand Show data source
Hydrophobicity(logP)
-3.1 expand Show data source
Storage Condition
-20°C Freezer, Under Inert Atmosphere expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00798 external link
Item Information
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

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Holt, H.A., et al.: J. Antimicrob. Chemother., 34, 747 (1994)
  • • Wilschanski, M., et al.: Am. J. Respir. Crit. Care Med., 161, 860 (1994)
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PATENTS

PATENTS

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