Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H18N2O4S.C14H15N |
| Molecular Weight | 531.666 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C(NCC1=CC=CC=C1)C2=CC=CC=C2.[H][C@]34SC(C)(C)[C@@H](N3C(=O)[C@H]4NC(=O)CC5=CC=CC=C5)C(O)=O
InChI
InChIKey=UPYLDHVPOPTZGP-LQDWTQKMSA-N
InChI=1S/C16H18N2O4S.C14H15N/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;1-3-7-13(8-4-1)11-15-12-14-9-5-2-6-10-14/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);1-10,15H,11-12H2/t11-,12+,14-;/m1./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 | C14H15N |
| Molecular Weight | 197.2756 |
| 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 |
|---|---|---|
| Penicillin-induced immune hemolytic anemia. Occurrence of massive intravascular hemolysis. | 1975 Aug 4 |
|
| The optimization test in the guinea-pig. A method for the predictive evaluation of the contact allergenicity of chemicals. | 1975 May |
|
| [Severe community-acquired pneumonia: etiology]. | 2001 |
|
| Optimisation of the prevention and treatment of bacterial endocarditis. | 2001 |
|
| Melatonin might be one possible medium of electroacupuncture anti-seizures. | 2001 |
|
| [Epidemiological survey for hemolytic streptococci isolated from children in Tokyo]. | 2001 Apr |
|
| Short-term effects of four antibiotics on DNA synthesis in endothelial cells. | 2001 Apr |
|
| Selection of metalloenzymes by catalytic activity using phage display and catalytic elution. | 2001 Apr 2 |
|
| [In vitro and in vivo activities of panipenem against penicillin-resistant Streptococcus pneumoniae]. | 2001 Jul |
|
| Degeneracy and additional alloreactivity of drug-specific human alpha beta(+) T cell clones. | 2001 Jul |
|
| Benzylpenicillin-induced prolonged cholestasis. | 2001 Jun |
|
| [Cellulitis and necrotizing fasciitis: microbiology and pathogenesis]. | 2001 Mar |
|
| 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 |
|
| Reaction of Lys-Tyr-Lys triad mimics with benzylpenicillin: insight into the role of Tyr150 in class C beta-lactamase. | 2001 May 7 |
|
| False penicillin resistance in Neisseria meningitidis following direct susceptibility tests from blood cultures. | 2001 Nov |
|
| [Treatment of acute bacterial meningitis]. | 2001 Nov 20 |
|
| Molecular dynamics simulations of the mononuclear zinc-beta-lactamase from Bacillus cereus complexed with benzylpenicillin and a quantum chemical study of the reaction mechanism. | 2001 Oct 10 |
|
| 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 |
|
| Diagnostic evaluation of a large group of patients with immediate allergy to penicillins: the role of skin testing. | 2001 Sep |
|
| The VanY(D) DD-carboxypeptidase of Enterococcus faecium BM4339 is a penicillin-binding protein. | 2001 Sep |
|
| Inhibition of translocation of beta -lactamase into the yeast endoplasmic reticulum by covalently bound benzylpenicillin. | 2001 Sep 14 |
|
| [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 |
|
| [Benzylpenicillin efficacy for neutropenic infection prophylaxis in patients with cancer and postcytostatic neutropenia]. | 2002 |
|
| Treatment of latent syphilis in HIV-infected patients with 10 d of benzylpenicillin G benethamine: a prospective study in Maputo, Mozambique. | 2002 |
|
| Gateways to Clinical Trials. | 2002 Apr |
|
| [The Pneumococcal Observatory for the Central Region, 1 April 1999 to 31 March 2000]. | 2002 Apr |
|
| 3: Community-acquired pneumonia. | 2002 Apr 1 |
|
| Immunoglobulin E binding determinants on beta-lactam drugs. | 2002 Aug |
|
| Cysteine is exported from the Escherichia coli cytoplasm by CydDC, an ATP-binding cassette-type transporter required for cytochrome assembly. | 2002 Dec 20 |
|
| 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 |
|
| Chloramphenicol versus benzylpenicillin and gentamicin for the treatment of severe pneumonia in children in Papua New Guinea: a randomised trial. | 2002 Feb 9 |
|
| Comparative in vitro activity of 16 antimicrobial agents against Actinobacillus pleuropneumoniae. | 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 |
|
| The 2.4-A crystal structure of the penicillin-resistant penicillin-binding protein PBP5fm from Enterococcus faecium in complex with benzylpenicillin. | 2002 Jul |
|
| Liquid chromatographic determination of ampicillin residues in porcine muscle tissue by a multipenicillin analytical method: European Collaborative Study. | 2002 Jul-Aug |
|
| Primary (isolated) meningococcal pericarditis. | 2002 Jun |
|
| Fatality after an injection of Bicillin into the tonsillar fossa during an adenotonsillectomy. | 2002 Mar |
|
| Functional involvement of rat organic anion transporter 3 (rOat3; Slc22a8) in the renal uptake of organic anions. | 2002 Mar |
|
| Expression and functional characterization of rat organic anion transporter 3 (rOat3) in the choroid plexus. | 2002 May |
|
| beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin. | 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 |
|
| Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. | 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 |
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
admin
on
Edited
Fri Dec 15 15:00:24 GMT 2023
by
admin
on
Fri Dec 15 15:00:24 GMT 2023
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| Record UNII |
AF5F3C86Z1
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| Record Status |
Validated (UNII)
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| Record Version |
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7173-27-5
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AF5F3C86Z1
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197868
Created by
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