U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H18N2O4S
Molecular Weight 334.3918
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENICILLIN G

SMILES

CC1(C)[C@]([H])(C(=O)O)N2C(=O)[C@]([H])([C@@]2([H])S1)N=C(Cc3ccccc3)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

HIDE SMILES / InChI

Molecular Formula C16H18N2O4S
Molecular Weight 334.3918
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
PENICILLIN G SODIUM

Approved Use

Penicillin 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 Date

9.8314558E11
Curative
PENICILLIN G SODIUM

Approved Use

Penicillin 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 Date

9.8314558E11
Curative
PENICILLIN G SODIUM

Approved Use

Penicillin 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 Date

9.8314558E11
Primary
PENICILLIN G SODIUM

Approved Use

Penicillin 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 Date

9.8314558E11
Primary
PENICILLIN G SODIUM

Approved Use

Penicillin 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 Date

9.8314558E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
4.1 day
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

Funbound

ValueDoseCo-administeredAnalytePopulation
65%
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[Penicillin induced haemolytic anaemia. Communication of a case (author's transl)].
1975
[Severe community-acquired pneumonia: etiology].
2001
Optimisation of the prevention and treatment of bacterial endocarditis.
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
Degeneracy and additional alloreactivity of drug-specific human alpha beta(+) T cell clones.
2001 Jul
Benzylpenicillin-induced prolonged cholestasis.
2001 Jun
Contribution of alveolar phagocytes to antibiotic efficacy in an experimental lung infection with Streptococcus pneumoniae.
2001 May
Interaction of 2,3-dimercapto-1-propane sulfonate with the human organic anion transporter hOAT1.
2001 Nov
[Treatment of acute bacterial meningitis].
2001 Nov 20
Purification and characterization of a beta-lactamase from Haemophilus ducreyi in Escherichia coli.
2001 Oct
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
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
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
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
[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
Amoxicillin-induced exanthema in young adults with infectious mononucleosis: demonstration of drug-specific lymphocyte reactivity.
2002 Dec
Cysteine is exported from the Escherichia coli cytoplasm by CydDC, an ATP-binding cassette-type transporter required for cytochrome assembly.
2002 Dec 20
[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
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
Natural antibiotic susceptibility and biochemical profiles of Yersinia enterocolitica-like strains: Y. bercovieri, Y. mollaretii, Y. aldovae and 'Y. ruckeri'.
2002 Jan
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
Functional involvement of rat organic anion transporter 3 (rOat3; Slc22a8) in the renal uptake of organic anions.
2002 Mar
Major role of organic anion transporter 3 in the transport of indoxyl sulfate in the kidney.
2002 May
Expression and functional characterization of rat organic anion transporter 3 (rOat3) in the choroid plexus.
2002 May
[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
Quality control of antibiotics before the implementation of an STD program in Northern Myanmar.
2002 Nov
Mechanism of the reduced elimination clearance of benzylpenicillin from cerebrospinal fluid in rats with intracisternal administration of lipopolysaccharide.
2002 Nov
[Antimicrobial susceptibility of Streptococcus pneumoniae and Haemophilus influenzae isolated in major hospitals in Nagano Prefecture].
2002 Oct
Fatal outcome from meningococcal disease--an association with meningococcal phenotype but not with reduced susceptibility to benzylpenicillin.
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
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
Patents

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 Sat Jun 26 10:28:36 UTC 2021
Edited
by admin
on Sat Jun 26 10:28:36 UTC 2021
Record UNII
Q42T66VG0C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PENICILLIN G
HSDB   MI   VANDF  
Common Name English
BENZYLPENICILLIN [INN]
Common Name English
PENICILLIN G [MI]
Common Name English
PHENOXYMETHYLPENICILLIN POTASSIUM IMPURITY A [EP]
Common Name English
BENZYLPENICILLIN [WHO-DD]
Common Name English
(2S,5R,6R)-3,3-DIMETHYL-7-OXO-6-(2-PHENYLACETAMIDO)-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
Systematic Name English
PENICILLIN G [VANDF]
Common Name English
PHENOXYMETHYLPENICILLIN IMPURITY A [EP]
Common Name English
J01CE01
Code English
BENZYLPENICILLIN
INN   MART.   WHO-DD  
INN  
Official Name English
NSC-193396
Code English
BENZYL PENICILLIN
Common Name English
PENICILLIN G [HSDB]
Common Name English
BENZYLPENICILLIN [MART.]
Common Name English
Classification Tree Code System Code
NDF-RT N0000011281
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
NDF-RT N0000011281
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
NCI_THESAURUS C1500
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
NDF-RT N0000011281
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
LIVERTOX 753
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
FDA ORPHAN DRUG 37689
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
WHO-ATC J01CE01
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
WHO-VATC QS01AA14
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
WHO-ATC J01CE09
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
WHO-VATC QJ51CE01
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
CFR 21 CFR 520.1696B
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
NDF-RT N0000011281
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
NDF-RT N0000175497
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
WHO-VATC QJ01CE01
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
FDA ORPHAN DRUG 18787
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
WHO-VATC QJ51RC22
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
NDF-RT N0000011281
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
NDF-RT N0000011281
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
NDF-RT N0000011281
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.2.1
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
NDF-RT N0000011281
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
WHO-ATC S01AA14
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
NDF-RT N0000011281
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
WHO-VATC QG51AG02
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL29
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-506-3
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY
MESH
D010400
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY
DRUG CENTRAL
2082
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY
CAS
61-33-6
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY
FDA UNII
Q42T66VG0C
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY
WIKIPEDIA
BENZYLPENICILLIN
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY
IUPHAR
4796
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY
NCI_THESAURUS
C61883
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY
EVMPD
SUB05772MIG
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY
DRUG BANK
DB01053
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY
MERCK INDEX
M8473
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY Merck Index
INN
58
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY
EPA CompTox
61-33-6
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY
LACTMED
Penicillin G
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY
PUBCHEM
5904
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY
HSDB
3166
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY
RXCUI
7980
Created by admin on Sat Jun 26 10:28:38 UTC 2021 , Edited by admin on Sat Jun 26 10:28:38 UTC 2021
PRIMARY RxNorm
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
EXCRETED UNCHANGED
URINE
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Cmax PHARMACOKINETIC ROUTE OF ADMINSTRATION
PHARMACOKINETIC
DOSE
PHARMACOKINETIC
Tmax
PHARMACOKINETIC