Tìm theo
Gentamicin
Các tên gọi khác (1) :
  • Gentamicin
Thuốc Gốc
Small Molecule
CAS: 1403-66-3
ATC: D06AX07, J01GB03, S01AA11, S02AA14, S03AA06
ĐG : Accutome Inc. , http://www.accutome.com
CTHH: C21H43N5O7
PTK: 477.5954
A complex of three different closely related aminoglycoside sulfates, Gentamicins C1, C2, and C1a, 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]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C21H43N5O7
Phân tử khối
477.5954
Monoisotopic mass
477.316248755
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
InChI Key
InChIKey=CEAZRRDELHUEMR-UHFFFAOYSA-N
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
Traditional 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
SMILES
CNC(C)C1CCC(N)C(OC2C(N)CC(N)C(OC3OCC(C)(O)C(NC)C3O)C2O)O1
Độ tan chảy
105 °C
Độ hòa tan
100 mg/mL
logP
-3.1
logS
-1.6
pKa (strongest acidic)
12.55
pKa (Strongest Basic)
10.18
PSA
199.73 Å2
Refractivity
118.02 m3·mol-1
Polarizability
51.92 Å3
Rotatable Bond Count
7
H Bond Acceptor Count
12
H Bond Donor Count
8
Physiological Charge
5
Number of Rings
3
Bioavailability
0
MDDR-Like Rule
true
Dược Lực Học : 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.
Cơ Chế Tác Dụng : A complex of three different closely related aminoglycoside sulfates, Gentamicins C1, C2, and C1a, 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] Aminoglycosides like gentamicin "irreversibly" bind to specific 30S-subunit proteins and 16S rRNA. Specifically gentamicin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes.
Dược Động Học :
▧ 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.
▧ Protein binding :
Low (between 0 and 30%)
▧ 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.
Độc Tính : 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.
Chỉ Định : 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).
Tương Tác Thuốc :
  • Atracurium The agent increases the effect of muscle relaxant
  • Bumetanide Increased ototoxicity
  • Cefamandole Increased risk of nephrotoxicity
  • Cefapirin Increased risk of nephrotoxicity
  • Cefazolin Increased risk of nephrotoxicity
  • Cefonicid Increased risk of nephrotoxicity
  • Cefoperazone Increased risk of nephrotoxicity
  • Ceforanide Increased risk of nephrotoxicity
  • Cefotaxime Increased risk of nephrotoxicity
  • Cefotetan Increased risk of nephrotoxicity
  • Cefoxitin Increased risk of nephrotoxicity
  • Cefradine Increased risk of nephrotoxicity
  • Ceftazidime Increased risk of nephrotoxicity
  • Ceftizoxime Increased risk of nephrotoxicity
  • Ceftriaxone Increased risk of nephrotoxicity
  • Cefuroxime Increased risk of nephrotoxicity
  • Cephalothin Group Increased risk of nephrotoxicity
  • Cisplatin Increased risk of nephrotoxicity
  • Colistimethate Aminoglycosides may enhance the nephrotoxic effect of Colistimethate. Aminoglycosides may enhance the neuromuscular-blocking effect of Colistimethate. Due to the potential for additive or synergistic toxicities (including both nephrotoxicity and neuromuscular blockade) between colistimethate and the aminoglycoside antibiotics, this combination should be avoided whenever possible. If these agents must be used together, patients' renal and neuromuscular function should be monitored closely.
  • Doxacurium chloride The agent increases the effect of muscle relaxant
  • Ethacrynic acid Increased ototoxicity
  • Furosemide Increased ototoxicity
  • Metocurine The agent increases the effect of muscle relaxant
  • Mivacurium The agent increases the effect of muscle relaxant
  • Pancuronium The agent increases the effect of muscle relaxant
  • Pipecuronium The agent increases the effect of muscle relaxant
  • Rocuronium The agent increases the effect of muscle relaxant
  • Succinylcholine The agent increases the effect of muscle relaxant
  • Tacrolimus Additive renal impairment may occur during concomitant therapy with aminoglycosides such as Gentamicin. Use caution during concomitant therapy.
  • Thalidomide Thalidomide increases the renal toxicity of the aminoglycoside
  • Ticarcillin Ticarcillin may reduce the serum concentration of Gentamicin. Ticarcillin may inactivate Gentamicin in vitro and the two agents should not be administered simultaneously through the same IV line.
  • Torasemide Increased ototoxicity
  • Tubocurarine The agent increases the effect of muscle relaxant
  • Vecuronium The agent increases the effect of muscle relaxant
Liều Lượng & Cách Dùng : Cream - Topical
Liquid - Ophthalmic
Ointment - Ophthalmic
Ointment - Topical
Solution - Auricular (otic)
Solution - Intravenous
Solution - Ophthalmic
Solution / drops - Auricular (otic)
Solution / drops - Ophthalmic
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Alcomicin
  • Công ty :
    Sản phẩm biệt dược : Bristagen
  • Công ty :
    Sản phẩm biệt dược : G-Mycin
  • Công ty : Schering-Plough
    Sản phẩm biệt dược : Garamycin
  • Công ty : Allergan
    Sản phẩm biệt dược : Genoptic
  • Công ty :
    Sản phẩm biệt dược : Gentacidin
  • Công ty :
    Sản phẩm biệt dược : Gentafair
  • Công ty : Akorn
    Sản phẩm biệt dược : Gentak
  • Công ty :
    Sản phẩm biệt dược : Gentamar
  • Công ty :
    Sản phẩm biệt dược : Jenamicin
  • Công ty :
    Sản phẩm biệt dược : Ocu-Mycin
  • Công ty :
    Sản phẩm biệt dược : Spectro-Genta
  • Công ty : U-Liang
    Sản phẩm biệt dược : U-gencin
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00798
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=3467
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506523
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C00505
ChemSpider
http://www.chemspider.com/Chemical-Structure.3348.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/17478-283-10
PharmGKB
http://www.pharmgkb.org/drug/PA449753
Wikipedia
http://en.wikipedia.org/wiki/Gentamicin
RxList
http://www.rxlist.com/cgi/generic2/pedgenta.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/gar1187.shtml
Drugs.com
http://www.drugs.com/cdi/gentamicin-drops.html
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