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

Details

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

SHOW SMILES / InChI
Structure of PENICILLIN G

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC3=CC=CC=C3)C(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

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
The optimization test in the guinea-pig. A method for the predictive evaluation of the contact allergenicity of chemicals.
1975 May
Fresh vs aged benzylpenicillin on non-IgE responses in mice.
1998 Jan
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
Drug-induced hemolysis: cefotetan-dependent hemolytic anemia mimicking an acute intravascular immune transfusion reaction.
2000 May
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
Selection of metalloenzymes by catalytic activity using phage display and catalytic elution.
2001 Apr 2
Novel periodontal drug delivery system for treatment of periodontitis.
2001 Apr 28
Substrate binding and catalytic mechanism of class B beta-lactamases: a molecular modelling study.
2001 Dec
[Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine].
2001 Feb
Degeneracy and additional alloreactivity of drug-specific human alpha beta(+) T cell clones.
2001 Jul
[Allergy to penicillin: facts and controversies].
2001 Jun
[Hoigne syndrome as an acute non-allergic reaction to different drugs: case reports].
2001 Jun
Benzylpenicillin-induced prolonged cholestasis.
2001 Jun
Contribution of alveolar phagocytes to antibiotic efficacy in an experimental lung infection with 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
[Treatment of acute bacterial meningitis].
2001 Nov 20
Antibiotic usage in Nordic countries.
2001 Sep
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
Marked differences in antibiotic use and resistance between university hospitals in Vilnius, Lithuania, and Huddinge, Sweden.
2001 Winter
Treatment of amatoxin poisoning: 20-year retrospective analysis.
2002
Antibiotics differ in their tendency to cause infusion phlebitis: a prospective observational study.
2002
[The Pneumococcal Observatory for the Central Region, 1 April 1999 to 31 March 2000].
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
Comparative in vitro activity of 16 antimicrobial agents against Actinobacillus pleuropneumoniae.
2002 Jan
Liquid chromatographic determination of ampicillin residues in porcine muscle tissue by a multipenicillin analytical method: European Collaborative Study.
2002 Jul-Aug
Fatality after an injection of Bicillin into the tonsillar fossa during an adenotonsillectomy.
2002 Mar
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.
2002 Nov
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 Fri Dec 15 14:58:04 UTC 2023
Edited
by admin
on Fri Dec 15 14:58:04 UTC 2023
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
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
BENZYLPENICILLIN
INN   MART.   WHO-DD  
INN  
Official Name 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 Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
NCI_THESAURUS C1500
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
LIVERTOX NBK547993
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
FDA ORPHAN DRUG 37689
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
WHO-ATC J01CE01
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
WHO-VATC QS01AA14
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
WHO-ATC J01CE09
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
WHO-VATC QJ51CE01
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
CFR 21 CFR 520.1696B
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
NDF-RT N0000175497
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
WHO-VATC QJ01CE01
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
FDA ORPHAN DRUG 18787
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
WHO-VATC QJ51RC22
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.2.1
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
WHO-ATC S01AA14
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
NDF-RT N0000011281
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
WHO-VATC QG51AG02
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
Code System Code Type Description
DAILYMED
Q42T66VG0C
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
ChEMBL
CHEMBL29
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-506-3
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
MESH
D010400
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
DRUG CENTRAL
2082
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
CAS
61-33-6
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
FDA UNII
Q42T66VG0C
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
NSC
193396
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
SMS_ID
100000091070
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
WIKIPEDIA
BENZYLPENICILLIN
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
IUPHAR
4796
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
NCI_THESAURUS
C61883
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
EVMPD
SUB05772MIG
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
DRUG BANK
DB01053
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
MERCK INDEX
m8473
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY Merck Index
INN
58
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
CHEBI
18208
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
EPA CompTox
DTXSID5046934
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
CHEBI
51354
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
LACTMED
Penicillin G
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
PUBCHEM
5904
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
HSDB
3166
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY
RXCUI
7980
Created by admin on Fri Dec 15 14:58:04 UTC 2023 , Edited by admin on Fri Dec 15 14:58:04 UTC 2023
PRIMARY RxNorm
Related Record Type Details
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
EXCRETED UNCHANGED
URINE
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
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
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