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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H17N2O4S.K
Molecular Weight 372.48
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENICILLIN G POTASSIUM

SMILES

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

InChI

InChIKey=IYNDLOXRXUOGIU-LQDWTQKMSA-M
InChI=1S/C16H18N2O4S.K/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);/q;+1/p-1/t11-,12+,14-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C16H17N2O4S
Molecular Weight 333.382
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula K
Molecular Weight 39.0983
Charge 1
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.

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-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
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
Optimisation of the prevention and treatment of bacterial endocarditis.
2001
Encouraging good antimicrobial prescribing practice: a review of antibiotic prescribing policies used in the South East Region of England.
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
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
Natural antibiotic susceptibility of strains of the Enterobacter cloacae complex.
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
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
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
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
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
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
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 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
3: Community-acquired pneumonia.
2002 Apr 1
Characterization of specific IgE response in vitro against protein and drug allergens using atopic and normal donors.
2002 Mar
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
[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
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 15:12:30 GMT 2023
Edited
by admin
on Fri Dec 15 15:12:30 GMT 2023
Record UNII
VL775ZTH4C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PENICILLIN G POTASSIUM
GREEN BOOK   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
PENICILLIN G POTASSIUM [USP MONOGRAPH]
Common Name English
POTASSIUM PENICILLIN G
Common Name English
PENICILLIN G POTASSIUM [USP-RS]
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-6-((PHENYLACETYL)AMINO)-, MONOPOTASSIUM SALT, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.))-
Common Name English
PENTIDS
Brand Name English
BENZYLPENICILLIN POTASSIUM [EP MONOGRAPH]
Common Name English
BENZYLPENICILLIN POTASSIUM [WHO-IP]
Common Name English
NSC-131815
Code English
POTASSIUM BENZYLPENICILLINATE
Common Name English
PENICILLIN G POTASSIUM [GREEN BOOK]
Common Name English
PENTIDS '200'
Brand Name English
BENZYLPENICILLIN POTASSIUM [JAN]
Common Name English
PENICILLIN G POTASSIUM SALT [MI]
Common Name English
Monopotassium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Systematic Name English
PFIZERPEN
Brand Name English
BENZYLPENICILLINIC ACID POTASSIUM SALT
Common Name English
BENZYLPENICILLIN POTASSIUM
EP   MART.   WHO-DD   WHO-IP  
Common Name English
BENZYLPENICILLIN POTASSIUM [MART.]
Common Name English
BENZYLPENICILLINUM KALICUM [WHO-IP LATIN]
Common Name English
PENICILLIN G POTASSIUM SALT
MI  
Common Name English
Benzylpenicillin potassium [WHO-DD]
Common Name English
PENICILLIN G POTASSIUM [VANDF]
Common Name English
PENICILLIN-2
Brand Name English
PENICILLIN G POTASSIUM [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
204-038-0
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
PRIMARY
NSC
131815
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
PRIMARY
FDA UNII
VL775ZTH4C
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
PRIMARY
NCI_THESAURUS
C47658
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
PRIMARY
DRUG BANK
DBSALT002390
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
PRIMARY
ChEMBL
CHEMBL29
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
PRIMARY
PUBCHEM
23664709
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
PRIMARY
MERCK INDEX
m8473
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
PRIMARY Merck Index
DAILYMED
VL775ZTH4C
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
PRIMARY
EVMPD
SUB13036MIG
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
PRIMARY
SMS_ID
100000092108
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
PRIMARY
CAS
113-98-4
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID7045106
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
PRIMARY
RS_ITEM_NUM
1502508
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
PENICILLIN G POTASSIUM
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
PRIMARY Description: A white or almost white, crystalline powder; odourless or with a faint characteristic odour. Solubility: Very soluble in water; practically insoluble in ether R. Category: Antibiotic. Storage: Benzylpenicillin potassium should be kept in a tightly closed container, protected from light, and stored at a temperaturenot exceeding 25?C. Labelling: The designation sterile Benzylpenicillin potassium indicates that the substance complies with the additionalrequirements for sterile Benzylpenicillin potassium and may be used for parenteral administration or for other sterile applications. Additional information: Benzylpenicillin potassium is moderately hygroscopic; it is readily decomposed by acids, alkalis andoxidizing agents. Even in the absence of light, Benzylpenicillin potassium is gradually degraded on exposure to a humidatmosphere, the decomposition being faster at higher temperatures. Definition: Benzylpenicillin potassium contains not less than 96.0% and not more than 102.0% of C16H17KN2O4S, calculated with reference to the dried substance.
RXCUI
203133
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
PRIMARY RxNorm
CHEBI
7963
Created by admin on Fri Dec 15 15:12:30 GMT 2023 , Edited by admin on Fri Dec 15 15:12:30 GMT 2023
PRIMARY
Related Record Type Details
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IMPURITY -> PARENT
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IMPURITY -> PARENT
IMPURITY -> PARENT
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IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
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IMPURITY -> PARENT
IMPURITY -> PARENT
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EP
Related Record Type Details
ACTIVE MOIETY
http://apps.who.int/phint/pdf/b/Jb.6.1.53.pdf