Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H17N2O4S.Na |
Molecular Weight | 356.372 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC3=CC=CC=C3)C([O-])=O
InChI
InChIKey=FCPVYOBCFFNJFS-LQDWTQKMSA-M
InChI=1S/C16H18N2O4S.Na/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);/q;+1/p-1/t11-,12+,14-;/m1./s1
Molecular Formula | C16H17N2O4S |
Molecular Weight | 333.382 |
Charge | -1 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Penicillin G, also known as benzylpenicillin, is a penicillin derivative commonly used in the form of its sodium or potassium salts in the treatment of a variety of infections. It is effective against most gram-positive bacteria and against gram-negative cocci. It is administered intravenously or intramuscularly due to poor oral absorption. Penicillin G may also be used in some cases as prophylaxis against susceptible organisms. Microbiology Penicillin G is bactericidal against penicillin-susceptible microorganisms during the stage of active multiplication. It acts by inhibiting biosynthesis of cell-wall mucopeptide. It is not active against the penicillinase-producing bacteria, which include many strains of staphylococci. Penicillin G is highly active in vitro against staphylococci (except penicillinase-producing strains), streptococci (groups A, B, C, G, H, L and M), pneumococci and Neisseria meningitidis. Other organisms susceptible in vitro to penicillin G are Neisseria gonorrhoeae, Corynebacterium diphtheriae, Bacillus anthracis, clostridia, Actinomyces species, Spirillum minus, Streptobacillus monillformis, Listeria monocytogenes, and leptospira; Treponema pallidum is extremely susceptible. Adverse effects can include hypersensitivity reactions including urticaria, fever, joint pains, rashes, angioedema, anaphylaxis, serum sickness-like reaction.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3245263 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | PENICILLIN G SODIUM Approved UsePenicillin G Sodium for Injection, USP is indicated in the treatment of serious infections caused by susceptible strains of the designated microorganisms. Appropriate culture and susceptibility tests should be done before treatment in order to isolate and identify organisms causing infection and to determine their susceptibility to penicillin G. Therapy with Penicillin G Sodium for Injection, USP may be initiated before results of such tests are known when there is reason to believe the infection may involve any of the organisms listed below, however, once these results become available, appropriate therapy should be continued Launch Date9.8314558E11 |
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Curative | PENICILLIN G SODIUM Approved UsePenicillin G Sodium for Injection, USP is indicated in the treatment of serious infections caused by susceptible strains of the designated microorganisms. Appropriate culture and susceptibility tests should be done before treatment in order to isolate and identify organisms causing infection and to determine their susceptibility to penicillin G. Therapy with Penicillin G Sodium for Injection, USP may be initiated before results of such tests are known when there is reason to believe the infection may involve any of the organisms listed below, however, once these results become available, appropriate therapy should be continued Launch Date9.8314558E11 |
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Curative | PENICILLIN G SODIUM Approved UsePenicillin G Sodium for Injection, USP is indicated in the treatment of serious infections caused by susceptible strains of the designated microorganisms. Appropriate culture and susceptibility tests should be done before treatment in order to isolate and identify organisms causing infection and to determine their susceptibility to penicillin G. Therapy with Penicillin G Sodium for Injection, USP may be initiated before results of such tests are known when there is reason to believe the infection may involve any of the organisms listed below, however, once these results become available, appropriate therapy should be continued Launch Date9.8314558E11 |
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Primary | PENICILLIN G SODIUM Approved UsePenicillin G Sodium for Injection, USP is indicated in the treatment of serious infections caused by susceptible strains of the designated microorganisms. Appropriate culture and susceptibility tests should be done before treatment in order to isolate and identify organisms causing infection and to determine their susceptibility to penicillin G. Therapy with Penicillin G Sodium for Injection, USP may be initiated before results of such tests are known when there is reason to believe the infection may involve any of the organisms listed below, however, once these results become available, appropriate therapy should be continued Launch Date9.8314558E11 |
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Primary | PENICILLIN G SODIUM Approved UsePenicillin G Sodium for Injection, USP is indicated in the treatment of serious infections caused by susceptible strains of the designated microorganisms. Appropriate culture and susceptibility tests should be done before treatment in order to isolate and identify organisms causing infection and to determine their susceptibility to penicillin G. Therapy with Penicillin G Sodium for Injection, USP may be initiated before results of such tests are known when there is reason to believe the infection may involve any of the organisms listed below, however, once these results become available, appropriate therapy should be continued Launch Date9.8314558E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
400 μg/mL |
5000000 unit single, intravenous dose: 5000000 unit route of administration: Intravenous experiment type: SINGLE co-administered: |
PENICILLIN G serum | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.1 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21991307/ |
1200000 unit single, intramuscular dose: 1200000 unit route of administration: Intramuscular experiment type: SINGLE co-administered: |
PENICILLIN G serum | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
65% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8218695/ |
12000000 unit 1 times / day steady-state, intravenous dose: 12000000 unit route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
PENICILLIN G plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
40% |
PENICILLIN G serum | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/22273603/ Page: 6.0 |
yes [IC50 102 uM] | |||
yes [IC50 25 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/22273603/ Page: 4.0 |
yes | |||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
[Penicillin induced haemolytic anaemia. Communication of a case (author's transl)]. | 1975 |
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Anaphylaxis manifested by hypotension alone. | 1975 Jan |
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Drug-induced hemolysis: cefotetan-dependent hemolytic anemia mimicking an acute intravascular immune transfusion reaction. | 2000 May |
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Routine prophylactic antibiotic use in the management of snakebite. | 2001 |
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Optimisation of the prevention and treatment of bacterial endocarditis. | 2001 |
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Melatonin might be one possible medium of electroacupuncture anti-seizures. | 2001 |
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Natural antibiotic susceptibility of strains of the Enterobacter cloacae complex. | 2001 Dec |
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Benzylpenicillin-induced prolonged cholestasis. | 2001 Jun |
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Antimicrobial susceptibilities of Erysipelothrix rhusiopathiae isolated from pigs with swine erysipelas in Japan, 1988-1998. | 2001 Mar |
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False penicillin resistance in Neisseria meningitidis following direct susceptibility tests from blood cultures. | 2001 Nov |
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[Treatment of acute bacterial meningitis]. | 2001 Nov 20 |
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Purification and characterization of a beta-lactamase from Haemophilus ducreyi in Escherichia coli. | 2001 Oct |
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Inhibition of translocation of beta -lactamase into the yeast endoplasmic reticulum by covalently bound benzylpenicillin. | 2001 Sep 14 |
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Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects. | 2001 Sep-Oct |
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Treatment of amatoxin poisoning: 20-year retrospective analysis. | 2002 |
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Antibiotics differ in their tendency to cause infusion phlebitis: a prospective observational study. | 2002 |
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Gateways to Clinical Trials. | 2002 Apr |
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[The Pneumococcal Observatory for the Central Region, 1 April 1999 to 31 March 2000]. | 2002 Apr |
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Amoxicillin-induced exanthema in young adults with infectious mononucleosis: demonstration of drug-specific lymphocyte reactivity. | 2002 Dec |
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Overexpression, purification and biochemical characterization of a class A high-molecular-mass penicillin-binding protein (PBP), PBP1* and its soluble derivative from Mycobacterium tuberculosis. | 2002 Feb 1 |
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The 2.4-A crystal structure of the penicillin-resistant penicillin-binding protein PBP5fm from Enterococcus faecium in complex with benzylpenicillin. | 2002 Jul |
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Major role of organic anion transporter 3 in the transport of indoxyl sulfate in the kidney. | 2002 May |
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beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin. | 2002 Nov |
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Minimum inhibitory concentrations of 20 antimicrobial agents against Staphylococcus aureus isolated from bovine intramammary infections in Japan. | 2002 Nov |
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Quality control of antibiotics before the implementation of an STD program in Northern Myanmar. | 2002 Nov |
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[Antimicrobial susceptibility of Streptococcus pneumoniae and Haemophilus influenzae isolated in major hospitals in Nagano Prefecture]. | 2002 Oct |
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Fatal outcome from meningococcal disease--an association with meningococcal phenotype but not with reduced susceptibility to benzylpenicillin. | 2002 Oct |
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Biochemical characterization of a novel extended-spectrum beta-lactamase from Pseudomonas aeruginosa 802. | 2002 Spring |
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Benzylpenicillin differentially conjugates to IFN-gamma, TNF-alpha, IL-1beta, IL-4 and IL-13 but selectively reduces IFN-gamma activity. | 2003 Feb |
Sample Use Guides
Serious infections due to susceptible strains of streptococci (including
S. pneumoniae): 5 to 24 million units/day depending on the infection and its severity administered in equally divided doses every 4 to 6 hours
Anthrax: Minimum of 8 million units/day in divided doses every 6 hours. Higher doses may be required depending on susceptibility of organism
Actinomycosis: 1 to 6 million units/day
Diphtheria (adjunctive therapy to antitoxin and for the prevention of the carrier state): 2 to 3 million units/day in divided doses for 10 to 12 days
Listeria infections, Meningitis: 15 to 20 million units/day for 2 weeks
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27511803
It was studied the antioxidant activity of penicillin G (PG) through its reactivity towards reactive oxygen species (superoxide anion radical, O2•̅; hydroxyl radical, HO• ; peroxyl radical, ROO• ; hydrogen peroxide, H2 O2 ; DPPH• ) using various in vitro antioxidant assays with chemiluminescence (CL) and spectrophotometry as measurement techniques. In hydroxyl radical assays , PG was found to inhibit the CL signal arising from the Fenton-like reaction in a dose-dependent manner with IC50 = 0.480 ± 0.020 mM. The highest reactivity of PG among the tested penicillins towards the HO radical was confirmed in the deoxyribose degradation assay.
Substance Class |
Chemical
Created
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admin
on
Edited
Wed Jul 05 22:44:11 UTC 2023
by
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on
Wed Jul 05 22:44:11 UTC 2023
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Record UNII |
YS5LY7JF4N
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C1500
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SUB13038MIG
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9900
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PENICILLIN G SODIUM
Created by
admin on Wed Jul 05 22:44:11 UTC 2023 , Edited by admin on Wed Jul 05 22:44:11 UTC 2023
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PRIMARY | Description: A white or almost white, crystalline powder; odourless or with a faint characteristic odour. Solubility: Soluble in about 0.5 part of water; practically insoluble in ether R. Category: Antibiotic. Storage: Benzylpenicillin sodium should be kept in a tightly closed container, protected from light, and stored at a temperature notexceeding 25?C. Labelling: The designation sterile Benzylpenicillin sodium indicates that the substance complies with the additional requirementsfor sterile Benzylpenicillin sodium and may be used for parenteral administration or for other sterile applications. Additional information: Benzylpenicillin sodium is hygroscopic; it is readily decomposed by acid, alkalis and oxidizing agents.Even in the absence of light, Benzylpenicillin sodium is gradually degraded on exposure to a humid atmosphere, thedecomposition being faster at higher temperatures. Definition: Benzylpenicillin sodium contains not less than 96.0% and not more than 102.0% of C16H17N2NaO4S, calculated withreference to the dried substance. | ||
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CHEMBL29
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23668834
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51765
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C28865
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DTXSID6040581
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100000091609
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PARENT -> SALT/SOLVATE |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
http://apps.who.int/phint/pdf/b/Jb.6.1.54.pdf
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