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 Date9.8314558E11 |
|||
| 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 |
|||
| 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 |
|||
| 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 |
|||
| 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 |
|---|---|---|---|
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 |
|---|---|---|
| Anaphylaxis manifested by hypotension alone. | 1975 Jan |
|
| Penicillin-induced haemolytic anaemia associated with microangiopathy. | 1976 Apr |
|
| Melatonin might be one possible medium of electroacupuncture anti-seizures. | 2001 |
|
| Successful shortening from seven to four days of parenteral beta-lactam treatment for common childhood infections: a prospective and randomized study. | 2001 |
|
| Selection of metalloenzymes by catalytic activity using phage display and catalytic elution. | 2001 Apr 2 |
|
| A theoretical study of the aminolysis reaction of lysine 199 of human serum albumin with benzylpenicillin: consequences for immunochemistry of penicillins. | 2001 Aug 8 |
|
| Substrate binding and catalytic mechanism of class B beta-lactamases: a molecular modelling study. | 2001 Dec |
|
| Gradient diffusion antibiotic susceptibility testing of potentially probiotic lactobacilli. | 2001 Dec |
|
| [Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine]. | 2001 Feb |
|
| 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 |
|
| Degeneracy and additional alloreactivity of drug-specific human alpha beta(+) T cell clones. | 2001 Jul |
|
| [Allergy to penicillin: facts and controversies]. | 2001 Jun |
|
| [Cellulitis and necrotizing fasciitis: microbiology and pathogenesis]. | 2001 Mar |
|
| Antimicrobial susceptibilities of Erysipelothrix rhusiopathiae isolated from pigs with swine erysipelas in Japan, 1988-1998. | 2001 Mar |
|
| 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 |
|
| Contribution of alveolar phagocytes to antibiotic efficacy in an experimental lung infection with 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 |
|
| Clinical evaluation of Pharmacia CAP System RAST FEIA amoxicilloyl and benzylpenicilloyl in patients with penicillin allergy. | 2001 Sep |
|
| Diagnostic evaluation of a large group of patients with immediate allergy to penicillins: the role of skin testing. | 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 |
|
| Treatment of amatoxin poisoning: 20-year retrospective analysis. | 2002 |
|
| Antibiotics differ in their tendency to cause infusion phlebitis: a prospective observational study. | 2002 |
|
| Treatment of latent syphilis in HIV-infected patients with 10 d of benzylpenicillin G benethamine: a prospective study in Maputo, Mozambique. | 2002 |
|
| [Difficulties with using T lymphocyte culture as a method for diagnosing allergies to benzylpenicillin]. | 2002 |
|
| Gateways to Clinical Trials. | 2002 Apr |
|
| [Post-marketing surveillance of antibacterial activities of cefozopran against various clinical isolates--I. Gram-positive bacteria]. | 2002 Feb |
|
| 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 |
|
| [Maximum residue levels (MRL's) of veterinary medicines in relation to food safety. MRL's really do matter--the Benzaprocpen case]. | 2002 Jan 1 |
|
| Primary (isolated) meningococcal pericarditis. | 2002 Jun |
|
| Fatality after an injection of Bicillin into the tonsillar fossa during an adenotonsillectomy. | 2002 Mar |
|
| 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 UTC 2023
by
admin
on
Fri Dec 15 15:00:24 UTC 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
Created by
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AF5F3C86Z1
Created by
admin on Fri Dec 15 15:00:24 UTC 2023 , Edited by admin on Fri Dec 15 15:00:24 UTC 2023
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197868
Created by
admin on Fri Dec 15 15:00:24 UTC 2023 , Edited by admin on Fri Dec 15 15:00:24 UTC 2023
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