Tìm theo
Ertapenem
Các tên gọi khác (3) :
  • (1R,5S,6S,8R,2'S,4's)-2-(2-(3-carboxyphenylcarbamoyl)pyrrolidin-4-ylthio)-6-(1-hydroxyethyl)-1-methylcarbapenem-3-carboxylic acid
  • (4R,5S,6S)-3-((3S,5S)-5-((3-Carboxyphenyl)carbamoyl)pyrrolidin-3-ylthio)-6-((R)-1-hydroxyethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  • ERTAPENEM
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 153832-46-3
ATC: J01DH03
ĐG : Merck & Co. , http://www.merck.com
CTHH: C22H25N3O7S
PTK: 475.515
Ertapenem is a carbapenem antibiotic marketed by Merck as Invanz®. It is structurally very similar to meropenem in that it possess a 1-beta-methyl group. [Wikipedia]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
Phân tử khối
475.515
Monoisotopic mass
475.141320859
InChI
InChI=1S/C22H25N3O7S/c1-9-16-15(10(2)26)20(28)25(16)17(22(31)32)18(9)33-13-7-14(23-8-13)19(27)24-12-5-3-4-11(6-12)21(29)30/h3-6,9-10,13-16,23,26H,7-8H2,1-2H3,(H,24,27)(H,29,30)(H,31,32)/t9-,10-,13+,14+,15-,16-/m1/s1
InChI Key
InChIKey=JUZNIMUFDBIJCM-ANEDZVCMSA-N
IUPAC Name
(4R,5S,6S)-3-{[(3S,5S)-5-[(3-carboxyphenyl)carbamoyl]pyrrolidin-3-yl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Traditional IUPAC Name
ertapenem
SMILES
[H][[email protected]]12[[email protected]@H](C)C(S[[email protected]]3([H])CN[[email protected]@]([H])(C3)C(=O)NC3=CC=CC(=C3)C(O)=O)=C(N1C(=O)[[email protected]]2([H])[[email protected]@H](C)O)C(O)=O
Độ hòa tan
Soluble as sodium salt
logP
0.3
logS
-3.2
pKa (strongest acidic)
3.37
pKa (Strongest Basic)
9.03
PSA
156.27 Å2
Refractivity
121.8 m3·mol-1
Polarizability
48.77 Å3
Rotatable Bond Count
7
H Bond Acceptor Count
8
H Bond Donor Count
5
Physiological Charge
-1
Number of Rings
4
Bioavailability
1
Rule of Five
true
MDDR-Like Rule
true
Dược Lực Học : Ertapenem has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria.
Cơ Chế Tác Dụng : Ertapenem is a carbapenem antibiotic marketed by Merck as Invanz®. It is structurally very similar to meropenem in that it possess a 1-beta-methyl group. [Wikipedia] The bactericidal activity of ertapenem results from the inhibition of cell wall synthesis and is mediated through ertapenem binding to penicillin binding proteins (PBPs). In Escherichia coli, it has strong affinity toward PBPs 1a, 1b, 2, 3, 4 and 5 with preference for PBPs 2 and 3. Ertapenem is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases. Ertapenem is hydrolyzed by metallo-beta-lactamases.
Dược Động Học :
▧ Absorption :
Ertapenem is almost completely absorbed following intramuscular administration. The bioavailability of a 1 g intramuscular dose approximated 92% in 26 healthy subjects [77% male; median (range) age, 29 (22–41) years]. Plasma concentrations of total ertapenem were similar whether given intramuscularly or intravenously.
▧ Volume of Distribution :
* 0.12 liter/kg [adults] * 0.2 liter/kg [pediatric, 3 months to 12 years] * 0.16 liter/kg [pediatric patients 13 to 17 years]
▧ Protein binding :
Ertapenem is highly bound to human plasma proteins, primarily albumin, in a concentration-dependent manner. The protein binding of ertapenem decreases as plasma concentrations increase. At a plasma concentration of <100 µg/mL, approximately 95% of ertapenem is protein bound. Protein binding of ertapenem decreases to approximately 85% at an approximate plasma concentration of 300 µg/mL.
▧ Metabolism :
The major metabolite is the inactive ring-opened derivative formed by hydrolysis of the β-lactam ring. Ertapenem did not inhibit metabolism mediated by cytochrome P450 (CYP) isoforms 1A2, 2C9, 2C19, 2D6, 2E1, or 3A4 when evaluated by in vitro studies in human liver microsomes. Ertapenem is neither a substrate nor an inhibitor of P-glycoprotein or cytochrome P450 enzymes; significant drug interactions between ertapenem and drugs handled by these systems are not expected [PMID: 15150180]
▧ Route of Elimination :
Of the 80% recovered in urine, approximately 38% is excreted as unchanged drug and approximately 37% as the ring-opened metabolite.
▧ Half Life :
The mean plasma half-life is approximately 4 hours.
▧ Clearance :
* 1.8 L/h
Chỉ Định : For the treatment the following moderate to severe infections caused by susceptible isolates of the designated microorganisms: (1) complicated intra-abdominal infections due to Escherichia coli, Clostridium clostridioforme, Eubacterium lentum, Peptostreptococcus species, Bacteroides fragilis, Bacteroides distasonis, Bacteroides ovatus, Bacteroides thetaiotaomicron, or Bacteroides uniformis, (2) complicated skin and skin structure infections, including diabetic foot infections without osteomyelitis due to Staphylococcus aureus (methicillin susceptible isolates only), Streptococcus agalactiae, Streptococcus pyogenes, Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Bacteroides fragilis, Peptostreptococcus species, Porphyromonas asaccharolytica, or Prevotella bivia, (3) community acquired pneumonia due to Streptococcus pneumoniae (penicillin susceptible isolates only) including cases with concurrent bacteremia, Haemophilus influenzae (beta-lactamase negative isolates only), or Moraxella catarrhalis, (4) complicated urinary tract infections including pyelonephritis due to Escherichia coli, including cases with concurrent bacteremia, or Klebsiella pneumoniae, (5) acute pelvic infections including postpartum endomyometritis, septic abortion and post surgical gynecologic infections due to Streptococcus agalactiae, Escherichia coli, Bacteroides fragilis, Porphyromonas asaccharolytica, Peptostreptococcus species, or Prevotella bivia.
Liều Lượng & Cách Dùng : Powder, for solution - Intravenous
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Invanz
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