Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H18N2O4S.C4H4N2 |
| Molecular Weight | 414.478 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1=CN=CN=C1.[H][C@]23SC(C)(C)[C@@H](N2C(=O)[C@H]3NC(=O)CC4=CC=CC=C4)C(O)=O
InChI
InChIKey=ZMZWDDSEAIEIPT-LQDWTQKMSA-N
InChI=1S/C16H18N2O4S.C4H4N2/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;1-2-5-4-6-3-1/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);1-4H/t11-,12+,14-;/m1./s1
| Molecular Formula | C4H4N2 |
| Molecular Weight | 80.088 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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 |
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 |
|---|---|---|
| [Penicillin induced haemolytic anaemia. Communication of a case (author's transl)]. | 1975 |
|
| Penicillin-induced immune hemolytic anemia. Occurrence of massive intravascular hemolysis. | 1975 Aug 4 |
|
| 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 |
|
| Routine prophylactic antibiotic use in the management of snakebite. | 2001 |
|
| Melatonin might be one possible medium of electroacupuncture anti-seizures. | 2001 |
|
| Encouraging good antimicrobial prescribing practice: a review of antibiotic prescribing policies used in the South East Region of England. | 2001 |
|
| Successful shortening from seven to four days of parenteral beta-lactam treatment for common childhood infections: a prospective and randomized study. | 2001 |
|
| [Epidemiological survey for hemolytic streptococci isolated from children in Tokyo]. | 2001 Apr |
|
| Gradient diffusion antibiotic susceptibility testing of potentially probiotic lactobacilli. | 2001 Dec |
|
| Structures of the acyl-enzyme complexes of the Staphylococcus aureus beta-lactamase mutant Glu166Asp:Asn170Gln with benzylpenicillin and cephaloridine. | 2001 Feb 27 |
|
| [CBO-guideline 'Bacterial meningitis']. | 2001 Feb 3 |
|
| Molecular dynamics study of the IIA binding site in human serum albumin: influence of the protonation state of Lys195 and Lys199. | 2001 Jan 18 |
|
| Epidemiology and diagnosis of meningitis: results of a five-year prospective, population-based study. | 2001 Jun |
|
| [Hoigne syndrome as an acute non-allergic reaction to different drugs: case reports]. | 2001 Jun |
|
| Contribution of alveolar phagocytes to antibiotic efficacy in an experimental lung infection with Streptococcus pneumoniae. | 2001 May |
|
| Comparative study of treatment with penicillin, ceftriaxone, trovafloxacin, quinupristin-dalfopristin and vancomycin in experimental endocarditis due to penicillin- and ceftriaxone-resistant Streptococcus pneumoniae. | 2001 May |
|
| False penicillin resistance in Neisseria meningitidis following direct susceptibility tests from blood cultures. | 2001 Nov |
|
| [The use of veterinary drugs during pregnancy of the dog]. | 2001 Nov 15 |
|
| Tetracycline-resistance genes of Clostridium perfringens, Clostridium septicum and Clostridium sordellii isolated from cattle affected with malignant edema. | 2001 Oct 22 |
|
| Antibiotic usage in Nordic countries. | 2001 Sep |
|
| Determination of benzylpenicillin, oxacillin, cloxacillin, and dicloxacillin in cows' milk by ion-pair high-performance liquid chromatography after precolumn derivatization. | 2001 Sep |
|
| Clinical evaluation of Pharmacia CAP System RAST FEIA amoxicilloyl and benzylpenicilloyl in patients with penicillin allergy. | 2001 Sep |
|
| [Allergic alteration of leukocytes in patients with drug intolerance]. | 2001 Sep-Oct |
|
| Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects. | 2001 Sep-Oct |
|
| Marked differences in antibiotic use and resistance between university hospitals in Vilnius, Lithuania, and Huddinge, Sweden. | 2001 Winter |
|
| [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 |
|
| [Difficulties with using T lymphocyte culture as a method for diagnosing allergies to benzylpenicillin]. | 2002 |
|
| Gateways to Clinical Trials. | 2002 Apr |
|
| [The Pneumococcal Observatory for the Central Region, 1 April 1999 to 31 March 2000]. | 2002 Apr |
|
| Immunoglobulin E binding determinants on beta-lactam drugs. | 2002 Aug |
|
| Amoxicillin-induced exanthema in young adults with infectious mononucleosis: demonstration of drug-specific lymphocyte reactivity. | 2002 Dec |
|
| Controlled administration of penicillin to patients with a positive history but negative skin and specific serum IgE tests. | 2002 Feb |
|
| Natural antibiotic susceptibility and biochemical profiles of Yersinia enterocolitica-like strains: Y. bercovieri, Y. mollaretii, Y. aldovae and 'Y. ruckeri'. | 2002 Jan |
|
| [Maximum residue levels (MRL's) of veterinary medicines in relation to food safety. MRL's really do matter--the Benzaprocpen case]. | 2002 Jan 1 |
|
| 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 |
|
| Quality control of antibiotics before the implementation of an STD program in Northern Myanmar. | 2002 Nov |
|
| Acyl-intermediate structures of the extended-spectrum class A beta-lactamase, Toho-1, in complex with cefotaxime, cephalothin, and benzylpenicillin. | 2002 Nov 29 |
|
| [Antimicrobial susceptibility of Streptococcus pneumoniae and Haemophilus influenzae isolated in major hospitals in Nagano Prefecture]. | 2002 Oct |
|
| Biochemical characterization of a novel extended-spectrum beta-lactamase from Pseudomonas aeruginosa 802. | 2002 Spring |
|
| 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
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admin
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Edited
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| Record UNII |
46917D13T1
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| Record Status |
Validated (UNII)
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| Record Version |
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DTXSID80208143
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59413-33-1
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46917D13T1
Created by
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