Tìm theo
Amikacin
Các tên gọi khác (10 ) :
  • 1-N-(L(-)-gamma-amino-alpha-Hydroxybutyryl)kanamycin a
  • Amicacin
  • Amiglyde-v
  • Amikacin
  • Amikacina
  • Amikacine
  • Amikacinum
  • Amikavet
  • Briclin
  • O-3-amino-3-Deoxy-alpha-D-glucopyranosyl-(1->4)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl-(1->6))-N(3)-(4-amino-L-2-hydroxybutyryl)-2-deoxy-L-streptamine
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 37517-28-5
ATC: D06AX12, J01GB06, S01AA21
ĐG : Bedford Labs , http://www.bedfordlabs.com
CTHH: C22H43N5O13
PTK: 585.6025
Amikacin is a semi-synthetic aminoglycoside antibiotic derived from kanamycin A. Similar to other aminoglycosides, amikacin disrupts bacterial protein synthesis by binding to the 30S ribosome of susceptible organisms. Binding interferes with mRNA binding and tRNA acceptor sites leading to the production of non-functional or toxic peptides. Other mechanisms not fully understood may confer the bactericidal effects of amikacin. Amikacin is also nephrotoxic and ototoxic.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C22H43N5O13
Phân tử khối
585.6025
Monoisotopic mass
585.285736487
InChI
InChI=1S/C22H43N5O13/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+/m0/s1
InChI Key
InChIKey=LKCWBDHBTVXHDL-RMDFUYIESA-N
IUPAC Name
(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2R,3R,4S,5S,6R)-6-(aminomethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-hydroxycyclohexyl]-2-hydroxybutanamide
Traditional IUPAC Name
amikacin
SMILES
NCC[C@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](N)[C@H]1O
Độ tan chảy
203-204 °C
Độ hòa tan
1.85E+005 mg/L (at 25 °C)
logP
-7.4
logS
-0.5
pKa (strongest acidic)
12.1
pKa (Strongest Basic)
9.79
PSA
331.94 Å2
Refractivity
129.84 m3·mol-1
Polarizability
58.2 Å3
Rotatable Bond Count
10
H Bond Acceptor Count
17
H Bond Donor Count
13
Physiological Charge
4
Number of Rings
3
Bioavailability
0
MDDR-Like Rule
true
Dược Lực Học : Amikacin is an 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 : Amikacin is a semi-synthetic aminoglycoside antibiotic derived from kanamycin A. Similar to other aminoglycosides, amikacin disrupts bacterial protein synthesis by binding to the 30S ribosome of susceptible organisms. Binding interferes with mRNA binding and tRNA acceptor sites leading to the production of non-functional or toxic peptides. Other mechanisms not fully understood may confer the bactericidal effects of amikacin. Amikacin is also nephrotoxic and ototoxic. Aminoglycosides like Amikacin "irreversibly" bind to specific 30S-subunit proteins and 16S rRNA. Amikacin inhibits protein synthesis by binding to the 30S ribosomal subunit to prevent the formation of an initiation complex with messenger RNA. Specifically Amikacin 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 :
Rapidly absorbed after intramuscular administration. Rapid absorption occurs from the peritoneum and pleura. Poor oral and topical absorption. Poorly absorbed from bladder irrigations and intrathecal administration.
▧ Volume of Distribution :
* 24 L [normal adult subjects]
▧ Protein binding :
0-11%
▧ Route of Elimination :
Amikacin is excreted primarily by glomerular filtration.
▧ Half Life :
2-3 hours
▧ Clearance :
* 100 mL/min
Độc Tính : Mild and reversible nephrotoxicity may be observed in 5 - 25% of patients. Amikacin accumulates in proximal renal tubular cells. 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.
Chỉ Định : For short-term treatment of serious infections due to susceptible strains of Gram-negative bacteria, including Pseudomonas species, Escherichia coli, species of indole-positive and indole-negative Proteus, Providencia species, Klebsiella-Enterobacter-Serratia species, and Acinetobacter (Mima-Herellea) species. Amikacin may also be used to treat Mycobacterium avium and Mycobacterium tuberculosis infections.
Tương Tác Thuốc :
  • Atracurium The agent increases the effect of muscle relaxant
  • Bumetanide Increased ototoxicity
  • Cefalotin Increased risk of nephrotoxicity
  • 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
  • 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 Amikacin. Use caution during concomitant therapy.
  • Thalidomide Thalidomide increases the renal toxicity of the aminoglycoside
  • Ticarcillin Ticarcillin may reduce the serum concentration of Amikacin. Ticarcillin may inactivate Amikacin 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 : Liquid - Intravenous
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty : Abbott
    Sản phẩm biệt dược : Amexel
  • Sản phẩm biệt dược : Amikin
  • Sản phẩm biệt dược : Amukin
  • Sản phẩm biệt dược : Biklin
  • Công ty : Brown & Burk
    Sản phẩm biệt dược : Erkacin
  • Sản phẩm biệt dược : Farcyclin
  • Công ty : Bros
    Sản phẩm biệt dược : Flexelite
  • Công ty : Bosch
    Sản phẩm biệt dược : Kamin
  • Sản phẩm biệt dược : Novamin
  • Công ty : Proel
    Sản phẩm biệt dược : Selaxa
  • Công ty : Medochemie
    Sản phẩm biệt dược : Selemycin
  • Công ty : Shiteh Organic
    Sản phẩm biệt dược : Sikacin
  • Công ty : T P Drug
    Sản phẩm biệt dược : Tipkin
  • Công ty : M & H
    Sản phẩm biệt dược : Tybikin
  • Công ty : Unimed Pharm
    Sản phẩm biệt dược : Ukaject
  • Công ty : Union
    Sản phẩm biệt dược : Unikin
  • Công ty : Rafarm
    Sản phẩm biệt dược : Uzix
  • Công ty : Epsilon
    Sản phẩm biệt dược : Xylanal
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00479
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=37768
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506386
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C06820
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D02543
ChemSpider
http://www.chemspider.com/Chemical-Structure.34635.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0703-9032-03
PharmGKB
http://www.pharmgkb.org/drug/PA164744372
Wikipedia
http://en.wikipedia.org/wiki/Amikacin
RxList
http://www.rxlist.com/cgi/generic3/amikacin.htm
Drugs.com
http://www.drugs.com/cdi/amikacin.html
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