Tìm theo
Aztreonam
Các tên gọi khác (7 ) :
  • (Z,)-2-((((2-Amino-4-thiazolyl)(((2S,3S,)-2-methyl-4-oxo-1-sulfo-3-azetidinyl)carbamoyl)methylene)amino)oxy)-2-methylpropionic acid
  • 2-({[(1Z)-1-(2-amino-1,3-thiazol-4-yl) -2- {[(2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl]amino} -2- oxoethylidene]amino}oxy)-2-methylpropanoic acid
  • Azactam
  • Aztreonam
  • Aztréonam
  • Aztreonamum
  • Primbactam
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 78110-38-0
ATC: J01DF01
ĐG : APP Pharmaceuticals , http://www.apppharma.com
CTHH: C13H17N5O8S2
PTK: 435.433
A monocyclic beta-lactam antibiotic originally isolated from Chromobacterium violaceum. It is resistant to beta-lactamases and is used in gram-negative infections, especially of the meninges, bladder, and kidneys. It may cause a superinfection with gram-positive organisms. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C13H17N5O8S2
Phân tử khối
435.433
Monoisotopic mass
435.051853925
InChI
InChI=1S/C13H17N5O8S2/c1-5-7(10(20)18(5)28(23,24)25)16-9(19)8(6-4-27-12(14)15-6)17-26-13(2,3)11(21)22/h4-5,7H,1-3H3,(H2,14,15)(H,16,19)(H,21,22)(H,23,24,25)/b17-8-/t5-,7-/m0/s1
InChI Key
InChIKey=WZPBZJONDBGPKJ-VEHQQRBSSA-N
IUPAC Name
(2S,3S)-3-[(2Z)-2-(2-azaniumyl-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-methyl-4-oxoazetidine-1-sulfonate
Traditional IUPAC Name
(2S,3S)-3-[(2Z)-2-(2-aminio-1,3-thiazol-4-yl)-2-[(1-carboxy-1-methylethoxy)imino]acetamido]-2-methyl-4-oxoazetidine-1-sulfonate
SMILES
C[C@H]1[C@H](NC(=O)C(=N/OC(C)(C)C(=O)O)\C2=CSC([NH3+])=N2)C(=O)N1S([O-])(=O)=O
Độ hòa tan
Insoluble
logP
-3.1
logS
-4.1
pKa (strongest acidic)
-1.9
pKa (Strongest Basic)
4.14
PSA
206.03 Å2
Refractivity
102.09 m3·mol-1
Polarizability
39.94 Å3
Rotatable Bond Count
6
H Bond Acceptor Count
10
H Bond Donor Count
3
Physiological Charge
-2
Number of Rings
2
Bioavailability
1
Rule of Five
true
Dược Lực Học : Aztreonam is a monocyclic beta-lactam antibiotic (a monobactam) originally isolated from Chromobacterium violaceum. Aztreonam exhibits potent and specific activity in vitro against a wide spectrum of gram-negative aerobic pathogens including Pseudomonas aeruginosa. It has no useful activity against gram-positive bacteria or anaerobes, but has very broad spectrum against gram-negative aerobes, including Pseudomonas aeruginosa. This has given it the nickname "the magic bullet for aerobic gram-negative bacteria". Aztreonam, unlike the majority of beta-lactam antibiotics, does not induce beta-lactamase activity and its molecular structure confers a high degree of resistance to hydrolysis by beta-lactamases (such as penicillinases and cephalosporinases) produced by most gram-negative and gram-positive pathogens; it is, therefore, usually active against gram-negative aerobic microorganisms that are resistant to antibiotics hydrolyzed by beta-lactamases. It is active against many strains that are multiply-resistant to other antibiotics, such as certain cephalosporins, penicillin, and aminoglycosides. Aztreonam maintains its antimicrobial activity over a pH range of 6 to 8 in vitro, as well as in the presence of human serum and under anaerobic conditions.
Cơ Chế Tác Dụng : A monocyclic beta-lactam antibiotic originally isolated from Chromobacterium violaceum. It is resistant to beta-lactamases and is used in gram-negative infections, especially of the meninges, bladder, and kidneys. It may cause a superinfection with gram-positive organisms. [PubChem] The bactericidal action of aztreonam results from the inhibition of bacterial cell wall synthesis due to a high affinity of aztreonam for penicillin binding protein 3 (PBP3). By binding to PBP3, aztreonam inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins. It is possible that aztreonam interferes with an autolysin inhibitor.
Dược Động Học :
▧ Absorption :
Less than 1% absorbed from the gastrointestinal tract following oral administration. Completely absorbed following intramuscular administration.
▧ Volume of Distribution :
* 12.6 L
▧ Protein binding :
Serum protein binding averaged 56% and is independent of dose. Impaired renal function, 36 to 43%.
▧ Metabolism :
Approximately 6 to 16% metabolized to inactive metabolites by hydrolysis of the beta-lactam bond, resulting in an open-ring compound.
▧ Route of Elimination :
In healthy subjects, aztreonam is excreted in the urine about equally by active tubular secretion and glomerular filtration. Urinary excretion of a single parenteral dose was essentially complete by 12 hours after injection.
▧ Half Life :
The serum half-life of aztreonam averaged 1.7 hours (1.5 to 2.0) in subjects with normal renal function, independent of the dose. In elderly patients and in patients with impaired renal function, the mean serum half-life of aztreonam increased (4.7 to 6 hours and 2.1 hours, respectively).
▧ Clearance :
* 91 mL/min [healthy]
Chỉ Định : For the treatment of the following infections caused by susceptible gram-negative microorganisms: urinary tract infections, lower respiratory tract infections, septicemia, skin and skin-structure infections, intra-abdominal infections, and gynecologic infections.
Tương Tác Thuốc :
Liều Lượng & Cách Dùng : Solution - Intravenous
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Sản phẩm biệt dược : Azactam
  • Công ty : Aristo
    Sản phẩm biệt dược : Azenam
  • Công ty : Shanxi C & Y
    Sản phẩm biệt dược : Aztram
  • Công ty : Zydus Cadila
    Sản phẩm biệt dược : Aztreo
  • Công ty : APP
    Sản phẩm biệt dược : Aztreonam
  • Công ty : AC Farma
    Sản phẩm biệt dược : Bencipen
  • Công ty : Gilead
    Sản phẩm biệt dược : Cayston
  • Công ty : Menarini
    Sản phẩm biệt dược : Primbactam
  • Công ty : Glenmark
    Sản phẩm biệt dược : Trezam
  • Công ty : Fahrenheit
    Sản phẩm biệt dược : Vebac
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00355
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C06840
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00240
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/51479-041-15
PharmGKB
http://www.pharmgkb.org/drug/PA448523
Wikipedia
http://en.wikipedia.org/wiki/Aztreonam
RxList
http://www.rxlist.com/cgi/generic4/azactaminj.htm
Drugs.com
http://www.drugs.com/cdi/aztreonam.html
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