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

Stereochemistry ABSOLUTE
Molecular Formula C16H18N2O4S
Molecular Weight 334.39
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENICILLIN G

SMILES

CC1(C)S[C@@H]2[C@H](NC(=O)CC3=CC=CC=C3)C(=O)N2[C@H]1C(O)=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 334.39
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.

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

2001
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

2001
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

2001
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

2001
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

2001
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 and cephalosporin biosynthesis: mechanism of carbon catabolite regulation of penicillin production.
1999 Jan-Feb
Successful shortening from seven to four days of parenteral beta-lactam treatment for common childhood infections: a prospective and randomized study.
2001
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
[CBO-guideline 'Bacterial meningitis'].
2001 Feb 3
Insights into the molecular basis for the carbenicillinase activity of PSE-4 beta-lactamase from crystallographic and kinetic studies.
2001 Jan 16
Molecular dynamics study of the IIA binding site in human serum albumin: influence of the protonation state of Lys195 and Lys199.
2001 Jan 18
[Hoigne syndrome as an acute non-allergic reaction to different drugs: case reports].
2001 Jun
Antimicrobial susceptibilities of Erysipelothrix rhusiopathiae isolated from pigs with swine erysipelas in Japan, 1988-1998.
2001 Mar
Interaction of 2,3-dimercapto-1-propane sulfonate with the human organic anion transporter hOAT1.
2001 Nov
[The use of veterinary drugs during pregnancy of the dog].
2001 Nov 15
[Allergic alteration of leukocytes in patients with drug intolerance].
2001 Sep-Oct
Treatment of amatoxin poisoning: 20-year retrospective analysis.
2002
Amoxicillin-induced exanthema in young adults with infectious mononucleosis: demonstration of drug-specific lymphocyte reactivity.
2002 Dec
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
[Maximum residue levels (MRL's) of veterinary medicines in relation to food safety. MRL's really do matter--the Benzaprocpen case].
2002 Jan 1
Evaluation of the new VITEK 2 system for determination of the susceptibility of clinical isolates of Streptococcus pneumoniae.
2002 Mar
Functional involvement of rat organic anion transporter 3 (rOat3; Slc22a8) in the renal uptake of organic anions.
2002 Mar
Quality control of antibiotics before the implementation of an STD program in Northern Myanmar.
2002 Nov
Fatal outcome from meningococcal disease--an association with meningococcal phenotype but not with reduced susceptibility to benzylpenicillin.
2002 Oct
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 Mon Mar 31 17:33:15 GMT 2025
Edited
by admin
on Mon Mar 31 17:33:15 GMT 2025
Record UNII
Q42T66VG0C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BENZYLPENICILLIN
INN   MART.   WHO-DD  
INN  
Preferred Name English
PENICILLIN G
HSDB   MI   VANDF  
Common Name English
benzylpenicillin [INN]
Common Name English
Benzylpenicillin [WHO-DD]
Common Name English
PENICILLIN G [MI]
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
J01CE01
Code English
NSC-193396
Code English
BENZYL PENICILLIN
Common Name English
PHENOXYMETHYLPENICILLIN POTASSIUM IMPURITY A [EP IMPURITY]
Common Name English
PHENOXYMETHYLPENICILLIN (BENZATHINE) TETRAHYDRATE IMPURITY A [EP IMPURITY]
Common Name English
PENICILLIN G [HSDB]
Common Name English
PHENOXYMETHYLPENICILLIN IMPURITY A [EP IMPURITY]
Common Name English
BENZYLPENICILLIN [MART.]
Common Name English
Classification Tree Code System Code
NDF-RT N0000011281
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
NDF-RT N0000011281
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
NCI_THESAURUS C1500
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
NDF-RT N0000011281
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
LIVERTOX NBK547993
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
FDA ORPHAN DRUG 37689
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
WHO-ATC J01CE01
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
WHO-VATC QS01AA14
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
WHO-ATC J01CE09
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
WHO-VATC QJ51CE01
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
CFR 21 CFR 520.1696B
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
NDF-RT N0000011281
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
NDF-RT N0000175497
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
WHO-VATC QJ01CE01
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
FDA ORPHAN DRUG 18787
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
WHO-VATC QJ51RC22
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
NDF-RT N0000011281
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
NDF-RT N0000011281
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
NDF-RT N0000011281
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.2.1
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
NDF-RT N0000011281
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
WHO-ATC S01AA14
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
NDF-RT N0000011281
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
WHO-VATC QG51AG02
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
Code System Code Type Description
DAILYMED
Q42T66VG0C
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
ChEMBL
CHEMBL29
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-506-3
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
MESH
D010400
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
DRUG CENTRAL
2082
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
CAS
61-33-6
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
FDA UNII
Q42T66VG0C
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
NSC
193396
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
SMS_ID
100000091070
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
WIKIPEDIA
BENZYLPENICILLIN
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
IUPHAR
4796
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
NCI_THESAURUS
C61883
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
EVMPD
SUB05772MIG
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
DRUG BANK
DB01053
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
MERCK INDEX
m8473
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY Merck Index
INN
58
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
CHEBI
18208
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
EPA CompTox
DTXSID5046934
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
CHEBI
51354
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
LACTMED
Penicillin G
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
PUBCHEM
5904
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
HSDB
3166
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY
RXCUI
7980
Created by admin on Mon Mar 31 17:33:15 GMT 2025 , Edited by admin on Mon Mar 31 17:33:15 GMT 2025
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
EXCRETED UNCHANGED
URINE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
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