Tìm theo
Benzylpenicillin
Các tên gọi khác (11 ) :
  • (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • 6-(2-phenylacetamido)penicillanic acid
  • Bencilpenicilina
  • Benzylpenicillin
  • Benzylpenicilline
  • Benzylpenicillinic acid
  • Benzylpenicillinum
  • Free penicillin ii
  • PCG
  • Penicillin G
  • PG
Thuốc Gốc
Small Molecule
CAS: 61-33-6
ATC: J01CE01, S01AA14
ĐG : APP Pharmaceuticals , http://www.apppharma.com
CTHH: C16H18N2O4S
PTK: 334.39
Benzylpenicillin (Penicillin G) is narrow spectrum antibiotic used to treat infections caused by susceptible bacteria. It is a natural penicillin antibiotic that is administered intravenously or intramuscularly due to poor oral absorption. Penicillin G may also be used in some cases as prophylaxis against susceptible organisms. Natural penicillins are considered the drugs of choice for several infections caused by susceptible gram positive aerobic organisms, such as Streptococcus pneumoniae, groups A, B, C and G streptococci, nonenterococcal group D streptococci, viridans group streptococci, and non-penicillinase producing staphylococcus. Aminoglycosides may be added for synergy against group B streptococcus (S. agalactiae), S. viridans, and Enterococcus faecalis. The natural penicillins may also be used as first or second line agents against susceptible gram positive aerobic bacilli such as Bacillus anthracis, Corynebacterium diphtheriae, and Erysipelothrix rhusiopathiae. Natural penicillins have limited activity against gram negative organisms; however, they may be used in some cases to treat infections caused by Neisseria meningitidis and Pasteurella. They are not generally used to treat anaerobic infections. Resistance patterns, susceptibility and treatment guidelines vary across regions.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C16H18N2O4S
Phân tử khối
334.39
Monoisotopic mass
334.098727764
InChI
InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1
InChI Key
InChIKey=JGSARLDLIJGVTE-MBNYWOFBSA-N
IUPAC Name
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Traditional IUPAC Name
penicillin G
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1)C(O)=O
Độ tan chảy
214-217 °C
Độ hòa tan
Slightly soluble (210 mg/L)
logP
1.83
logS
-3.1
pKa (strongest acidic)
3.53
pKa (Strongest Basic)
-2.6
PSA
86.71 Å2
Refractivity
84.53 m3·mol-1
Polarizability
33.54 Å3
Rotatable Bond Count
4
H Bond Acceptor Count
4
H Bond Donor Count
2
Physiological Charge
-1
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
pKa
2.74 (at 25 °C)
Dược Lực Học : Penicillin G is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Penicillin G has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of penicillin G results from the inhibition of cell wall synthesis and is mediated through penicillin G binding to penicillin binding proteins (PBPs). Penicillin G is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
Cơ Chế Tác Dụng : Benzylpenicillin (Penicillin G) is narrow spectrum antibiotic used to treat infections caused by susceptible bacteria. It is a natural penicillin antibiotic that is administered intravenously or intramuscularly due to poor oral absorption. Penicillin G may also be used in some cases as prophylaxis against susceptible organisms. Natural penicillins are considered the drugs of choice for several infections caused by susceptible gram positive aerobic organisms, such as Streptococcus pneumoniae, groups A, B, C and G streptococci, nonenterococcal group D streptococci, viridans group streptococci, and non-penicillinase producing staphylococcus. Aminoglycosides may be added for synergy against group B streptococcus (S. agalactiae), S. viridans, and Enterococcus faecalis. The natural penicillins may also be used as first or second line agents against susceptible gram positive aerobic bacilli such as Bacillus anthracis, Corynebacterium diphtheriae, and Erysipelothrix rhusiopathiae. Natural penicillins have limited activity against gram negative organisms; however, they may be used in some cases to treat infections caused by Neisseria meningitidis and Pasteurella. They are not generally used to treat anaerobic infections. Resistance patterns, susceptibility and treatment guidelines vary across regions. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, penicillin G 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 penicillin G interferes with an autolysin inhibitor.
Dược Động Học :
▧ Absorption :
Rapidly absorbed following both intramuscular and subcutaneous injection. Initial blood levels following parenteral administration are high but transient. Oral absorption in fasting, healthy humans is only about 15-30% as it is very susceptible to acid-catalyzed hydrolysis.
▧ Volume of Distribution :
0.53–0.67 L/kg in adults with normal renal function
▧ Protein binding :
Bind to serum proteins (45-68%), mainly albumin.
▧ Metabolism :
About 16-30% of an intramuscular dose is metabolized to penicilloic acid, an inactive metabolite. Small amounts of 6-aminopenicillanic acid have been recovered in the urine of patients on penicillin G. A small percentage of the drug appears to be hydroxylated into one or more active metabolites, which are also excreted via urine.
▧ Route of Elimination :
Penicillin G is eliminated by the kidneys. Nonrenal clearance includes hepatic metabolism and, to a lesser extent, biliary excretion.
▧ Half Life :
In adults with normal renal function is reportedly 0.4–0.9 hours
▧ Clearance :
560ml/min in healthy humans
Độc Tính : Oral LD50 in rat is 8900 mk/kg. Neurological adverse reactions, including convulsions, may occur with the attainment of high CSF levels of beta-lactams. Neutropenia can occur if high doses are administered consistently for over 2 weeks.
Chỉ Định : For use in the treatment of severe infections caused by penicillin G-susceptible microorganisms when rapid and high penicillin levels are required such as in the treatment of septicemia, meningitis, pericarditis, endocarditis and severe pneumonia.
Tương Tác Thuốc :
Liều Lượng & Cách Dùng : Powder, for solution - Intramuscular
Powder, for solution - Intravenous
Powder, for solution - Oral
Suspension - Oral
Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Pentids
  • Công ty :
    Sản phẩm biệt dược : Pfizerpen
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB01053
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=5904
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46506778
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C05551
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D02336
ChemSpider
http://www.chemspider.com/Chemical-Structure.5693.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0338-1021-41
PharmGKB
http://www.pharmgkb.org/drug/PA450842
RxList
http://www.rxlist.com/cgi/generic3/pengk.htm
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