Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H18N2O4S |
Molecular Weight | 334.39 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC3=CC=CC=C3)C(O)=O
InChI
InChIKey=JGSARLDLIJGVTE-MBNYWOFBSA-N
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
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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Penicillin-induced immune hemolytic anemia. Occurrence of massive intravascular hemolysis. | 1975 Aug 4 |
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Fresh vs aged benzylpenicillin on non-IgE responses in mice. | 1998 Jan |
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Dual inhibitory activity of sitafloxacin (DU-6859a) against DNA gyrase and topoisomerase IV of Streptococcus pneumoniae. | 1999 Oct |
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Haemorrhagic cystitis and renal dysfunction associated with high dose benzylpenicillin. | 2000 Jan |
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Melatonin might be one possible medium of electroacupuncture anti-seizures. | 2001 |
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[Epidemiological survey for hemolytic streptococci isolated from children in Tokyo]. | 2001 Apr |
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Short-term effects of four antibiotics on DNA synthesis in endothelial cells. | 2001 Apr |
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Structures of the acyl-enzyme complexes of the Staphylococcus aureus beta-lactamase mutant Glu166Asp:Asn170Gln with benzylpenicillin and cephaloridine. | 2001 Feb 27 |
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Degeneracy and additional alloreactivity of drug-specific human alpha beta(+) T cell clones. | 2001 Jul |
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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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Application of ion-exchange cartridge clean-up in food analysis IV. Confirmatory assay of benzylpenicillin, phenoxymethylpenicillin, oxacillin, cloxacillin, nafcillin and dicloxacillin, in bovine tissues by liquid chromatography-electrospray ionization tandem mass spectrometry. | 2001 Mar 16 |
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[The use of veterinary drugs during pregnancy of the dog]. | 2001 Nov 15 |
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Purification and characterization of a beta-lactamase from Haemophilus ducreyi in Escherichia coli. | 2001 Oct |
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The penicillin resistance of Enterococcus faecalis JH2-2r results from an overproduction of the low-affinity penicillin-binding protein PBP4 and does not involve a psr-like gene. | 2001 Sep |
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[Allergic alteration of leukocytes in patients with drug intolerance]. | 2001 Sep-Oct |
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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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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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Immunoglobulin E binding determinants on beta-lactam drugs. | 2002 Aug |
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Primary (isolated) meningococcal pericarditis. | 2002 Jun |
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Fatality after an injection of Bicillin into the tonsillar fossa during an adenotonsillectomy. | 2002 Mar |
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Expression and functional characterization of rat organic anion transporter 3 (rOat3) in the choroid plexus. | 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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Fatal outcome from meningococcal disease--an association with meningococcal phenotype but not with reduced susceptibility to benzylpenicillin. | 2002 Oct |
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Insights into the acylation mechanism of class A beta-lactamases from molecular dynamics simulations of the TEM-1 enzyme complexed with benzylpenicillin. | 2003 Jan 22 |
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.
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000011281
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NDF-RT |
N0000011281
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NCI_THESAURUS |
C1500
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NDF-RT |
N0000011281
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LIVERTOX |
NBK547993
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FDA ORPHAN DRUG |
37689
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WHO-ATC |
J01CE01
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WHO-VATC |
QS01AA14
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WHO-ATC |
J01CE09
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WHO-VATC |
QJ51CE01
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CFR |
21 CFR 520.1696B
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NDF-RT |
N0000011281
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NDF-RT |
N0000175497
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WHO-VATC |
QJ01CE01
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FDA ORPHAN DRUG |
18787
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WHO-VATC |
QJ51RC22
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NDF-RT |
N0000011281
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NDF-RT |
N0000011281
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NDF-RT |
N0000011281
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WHO-ESSENTIAL MEDICINES LIST |
6.2.1
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NDF-RT |
N0000011281
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WHO-ATC |
S01AA14
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NDF-RT |
N0000011281
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WHO-VATC |
QG51AG02
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Code System | Code | Type | Description | ||
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Q42T66VG0C
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PRIMARY | |||
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CHEMBL29
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200-506-3
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D010400
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2082
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61-33-6
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Q42T66VG0C
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193396
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100000091070
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BENZYLPENICILLIN
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4796
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C61883
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SUB05772MIG
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DB01053
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m8473
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PRIMARY | Merck Index | ||
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58
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18208
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DTXSID5046934
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51354
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Penicillin G
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5904
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3166
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7980
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PRIMARY | RxNorm |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
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SALT/SOLVATE (PARENT)