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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.

• Apothecon inc div bristol myers squibb
• Apothecon sub bristol myers squibb co
• App pharmaceuticals llc
• Baxter healthcare corp
• Bristol myers squibb spa
• Consolidated pharmaceutical group inc
• Eli lilly and co
• Gc hanford manufacturing co
• Ivax pharmaceuticals inc sub teva pharmaceuticals usa
• John d copanos and co inc
• King pharmaceuticals inc
• Marsam pharmaceuticals llc
• Mylan pharmaceuticals inc
• Parke davis div warner lambert co
• Pfizer laboratories div pfizer inc
• Pharmacia and upjohn co
• Purepac pharmaceutical co
• Sandoz inc
• Teva pharmaceuticals usa inc
• Wyeth ayerst laboratories

• APP Pharmaceuticals
• Baxter International Inc.
• C.O. Truxton Inc.
• King Pharmaceuticals Inc.
• Pfizer Inc.
• Physicians Total Care Inc.
• Sandoz

Synthesis Reference	Not Available
General Reference	Eagle H, Newman E, Musselman AD, Robinson M, Birmingham M: THE RENAL CLEARANCE OF PENICILLINS F, G, K, AND X IN RABBITS AND MAN. J Clin Invest. 1947 Sep;26(5):903-18. Pubmed

Type	small molecule

Classes

Penicillins Phenethylamines

Substructures

Hydroxy Compounds Acetates Amino Ketones Benzene and Derivatives Aliphatic and Aryl Amines Carboxylic Acids and Derivatives Beta Lactams Penicillins Thiazoles Phenethylamines Heterocyclic compounds Aromatic compounds Carboxamides and Derivatives Lactams Azetidines Thiazolidines

antibacterials 抗细菌;

Indication	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.
Pharmacodynamics	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.
Mechanism of action	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.
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. Important The metabolism module of DrugBank is currently in beta. Questions or suggestions? Please contact us. Substrate Enzymes Product Penicillin G 6-aminopenicillanic acid Details Penicillin G Penicilloic acid Details
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
Toxicity	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.
Affected organisms	Enteric bacteria and other eubacteria
Pathways	Not Available

Properties
State	solid
Experimental Properties	Property Value Source melting point 214-217 °C Not Available water solubility Slightly soluble (210 mg/L) Not Available logP 1.83 HANSCH,C ET AL. (1995) pKa 2.74 (at 25 °C) MERCK INDEX (1996)
Predicted Properties	Property Value Source water solubility 2.85e-01 g/l ALOGPS logP 1.92 ALOGPS logP 1.08 ChemAxon logS -3.1 ALOGPS pKa (strongest acidic) 3.53 ChemAxon pKa (strongest basic) -2.6 ChemAxon physiological charge -1 ChemAxon hydrogen acceptor count 4 ChemAxon hydrogen donor count 2 ChemAxon polar surface area 86.71 ChemAxon rotatable bond count 4 ChemAxon refractivity 84.53 ChemAxon polarizability 33.54 ChemAxon

Drug	Interaction
Demeclocycline	Possible antagonism of action
Doxycycline	Possible antagonism of action
Mesoridazine	Increased risk of cardiotoxicity and arrhythmias
Mestranol	This anti-infectious agent could decreases the effect of the oral contraceptive
Methacycline	Possible antagonism of action
Methotrexate	The penicillin increases the effect and toxicity of methotrexate
Minocycline	Possible antagonism of action
Oxytetracycline	Possible antagonism of action
Rolitetracycline	Possible antagonism of action
Tetracycline	Possible antagonism of action
Thioridazine	Increased risk of cardiotoxicity and arrhythmias

Not Available