Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H20N2.2C16H18N2O4S.4H2O |
| Molecular Weight | 981.185 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.O.C(CNCC1=CC=CC=C1)NCC2=CC=CC=C2.CC3(C)S[C@@H]4[C@H](NC(=O)CC5=CC=CC=C5)C(=O)N4[C@H]3C(O)=O.CC6(C)S[C@@H]7[C@H](NC(=O)CC8=CC=CC=C8)C(=O)N7[C@H]6C(O)=O
InChI
InChIKey=WIDKTXGNSOORHA-CJHXQPGBSA-N
InChI=1S/2C16H18N2O4S.C16H20N2.4H2O/c2*1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9;1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16;;;;/h2*3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);1-10,17-18H,11-14H2;4*1H2/t2*11-,12+,14-;;;;;/m11...../s1
| Molecular Formula | C16H18N2O4S |
| Molecular Weight | 334.39 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | C16H20N2 |
| Molecular Weight | 240.3434 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| 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 |
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 Date2001 |
|||
| 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 Date2001 |
|||
| 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 Date2001 |
|||
| 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 Date2001 |
|||
| 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 Date2001 |
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 |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| no | ||||
Page: 6.0 |
yes [IC50 102 uM] | |||
| yes [IC50 25 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Page: 4.0 |
yes | |||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The optimization test in the guinea-pig. A method for the predictive evaluation of the contact allergenicity of chemicals. | 1975 May |
|
| Penicillin-induced haemolytic anaemia associated with microangiopathy. | 1976 Apr |
|
| Fresh vs aged benzylpenicillin on non-IgE responses in mice. | 1998 Jan |
|
| Penicillin and cephalosporin biosynthesis: mechanism of carbon catabolite regulation of penicillin production. | 1999 Jan-Feb |
|
| Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. | 1999 May 7 |
|
| Dual inhibitory activity of sitafloxacin (DU-6859a) against DNA gyrase and topoisomerase IV of Streptococcus pneumoniae. | 1999 Oct |
|
| Haemorrhagic cystitis and renal dysfunction associated with high dose benzylpenicillin. | 2000 Jan |
|
| Drug-induced hemolysis: cefotetan-dependent hemolytic anemia mimicking an acute intravascular immune transfusion reaction. | 2000 May |
|
| Routine prophylactic antibiotic use in the management of snakebite. | 2001 |
|
| Optimisation of the prevention and treatment of bacterial endocarditis. | 2001 |
|
| [Epidemiological survey for hemolytic streptococci isolated from children in Tokyo]. | 2001 Apr |
|
| Substrate binding and catalytic mechanism of class B beta-lactamases: a molecular modelling study. | 2001 Dec |
|
| [In vitro and in vivo activities of panipenem against penicillin-resistant Streptococcus pneumoniae]. | 2001 Jul |
|
| Epidemiology and diagnosis of meningitis: results of a five-year prospective, population-based study. | 2001 Jun |
|
| 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 |
|
| [The use of veterinary drugs during pregnancy of the dog]. | 2001 Nov 15 |
|
| Purification and characterization of a beta-lactamase from Haemophilus ducreyi in Escherichia coli. | 2001 Oct |
|
| Antibiotic usage in Nordic countries. | 2001 Sep |
|
| The VanY(D) DD-carboxypeptidase of Enterococcus faecium BM4339 is a penicillin-binding protein. | 2001 Sep |
|
| 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 |
|
| [Allergic alteration of leukocytes in patients with drug intolerance]. | 2001 Sep-Oct |
|
| [Benzylpenicillin efficacy for neutropenic infection prophylaxis in patients with cancer and postcytostatic neutropenia]. | 2002 |
|
| Treatment of amatoxin poisoning: 20-year retrospective analysis. | 2002 |
|
| Antibiotics differ in their tendency to cause infusion phlebitis: a prospective observational study. | 2002 |
|
| 3: Community-acquired pneumonia. | 2002 Apr 1 |
|
| 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 |
|
| Liquid chromatographic determination of ampicillin residues in porcine muscle tissue by a multipenicillin analytical method: European Collaborative Study. | 2002 Jul-Aug |
|
| Improved brain delivery of benzylpenicillin with a peptide-vector-mediated strategy. | 2002 Jun |
|
| Characterization of specific IgE response in vitro against protein and drug allergens using atopic and normal donors. | 2002 Mar |
|
| Evaluation of the new VITEK 2 system for determination of the susceptibility of clinical isolates of Streptococcus pneumoniae. | 2002 Mar |
|
| [Use of antibiotics in general practice and at the Clinic for Infectious Diseases]. | 2002 May-Jun |
|
| beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin. | 2002 Nov |
|
| Minimum inhibitory concentrations of 20 antimicrobial agents against Staphylococcus aureus isolated from bovine intramammary infections in Japan. | 2002 Nov |
|
| [Antimicrobial susceptibility of Streptococcus pneumoniae and Haemophilus influenzae isolated in major hospitals in Nagano Prefecture]. | 2002 Oct |
|
| Benzylpenicillin differentially conjugates to IFN-gamma, TNF-alpha, IL-1beta, IL-4 and IL-13 but selectively reduces IFN-gamma activity. | 2003 Feb |
|
| High-performance thin-layer chromatography-bioautography for multiple antibiotic residues in cow's milk. | 2003 Feb 5 |
|
| 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
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
by
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on
Edited
Mon Mar 31 17:34:03 GMT 2025
by
admin
on
Mon Mar 31 17:34:03 GMT 2025
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| Record UNII |
RIT82F58GK
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| Record Status |
Validated (UNII)
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| Record Version |
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WHO-ESSENTIAL MEDICINES LIST |
6.2.1
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WHO-ATC |
J01CE08
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CFR |
21 CFR 522.1696A
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WHO-VATC |
QJ51RC24
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NCI_THESAURUS |
C1500
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WHO-VATC |
QJ01CE08
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RIT82F58GK
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4347
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Benzathine Penicillin G
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CHEMBL29
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D010401
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1502009
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SUB37626
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DTXSID00194317
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RIT82F58GK
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7982
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100000129194
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656811
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m8475
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41372-02-5
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BENZATHINE BENZYLPENICILLIN
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C47657
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DBSALT002769
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51352
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SUB05741MIG
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PRIMARY |
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PARENT -> SALT/SOLVATE | |||
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ANHYDROUS->SOLVATE |
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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IMPURITY -> PARENT |
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![Structure of (4S)-2-[2-[benzyl-[2-(benzylamino)ethyl]amino]-2-oxo-1-[(2-phenylacetyl)amino]ethyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid](/img/539071f1-10ec-45f9-b0fd-e290139d3565.svg "Structure of (4S)-2-[2-[benzyl-[2-(benzylamino)ethyl]amino]-2-oxo-1-[(2-phenylacetyl)amino]ethyl]-5,5-dimethyl-thiazolidine-4-carboxylic acid")
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ACTIVE MOIETY |