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

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H17N2O4S.Na
Molecular Weight 356.372
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENICILLIN G SODIUM

SMILES

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

InChI

InChIKey=FCPVYOBCFFNJFS-LQDWTQKMSA-M
InChI=1S/C16H18N2O4S.Na/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 Na
Molecular Weight 22.9898
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 haemolytic anaemia. Communication of a case (author's transl)].
1975
Penicillin-induced immune hemolytic anemia. Occurrence of massive intravascular hemolysis.
1975 Aug 4
Routine prophylactic antibiotic use in the management of snakebite.
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
Natural antibiotic susceptibility of strains of the Enterobacter cloacae complex.
2001 Dec
Epidemiology and diagnosis of meningitis: results of a five-year prospective, population-based study.
2001 Jun
[Allergy to penicillin: facts and controversies].
2001 Jun
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
Interaction of 2,3-dimercapto-1-propane sulfonate with the human organic anion transporter hOAT1.
2001 Nov
Tetracycline-resistance genes of Clostridium perfringens, Clostridium septicum and Clostridium sordellii isolated from cattle affected with malignant edema.
2001 Oct 22
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
Diagnostic evaluation of a large group of patients with immediate allergy to penicillins: the role of skin testing.
2001 Sep
The penicillin resistance of Enterococcus faecalis JH2-2r results from an overproduction of the low-affinity penicillin-binding protein PBP4 and does not involve a psr-like gene.
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
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
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
3: Community-acquired pneumonia.
2002 Apr 1
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
Controlled administration of penicillin to patients with a positive history but negative skin and specific serum IgE tests.
2002 Feb
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
Improved brain delivery of benzylpenicillin with a peptide-vector-mediated strategy.
2002 Jun
Primary (isolated) meningococcal pericarditis.
2002 Jun
Fatality after an injection of Bicillin into the tonsillar fossa during an adenotonsillectomy.
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
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 Fri Dec 15 15:12:39 GMT 2023
Edited
by admin
on Fri Dec 15 15:12:39 GMT 2023
Record UNII
YS5LY7JF4N
Record Status Validated (UNII)
Record Version
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Name Type Language
PENICILLIN G SODIUM
ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
BENZYLPENICILLIN SODIUM [EP IMPURITY]
Common Name English
PENICILLIN SODIUM
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-6-((PHENYLACETYL)AMINO)-, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.))-, MONOSODIUM SALT
Common Name English
PENICILLIN G SODIUM SALT
MI  
Common Name English
PENICILLINUM [HPUS]
Common Name English
BENZYLPENICILLIN SODIUM [MART.]
Common Name English
Benzylpenicillin sodium [WHO-DD]
Common Name English
SODIUM BENZYLPENICILLINOATE
Common Name English
CRYSTAPEN
Common Name English
BENZYLPENICILLIN SODIUM
EP   MART.   WHO-DD   WHO-IP  
Common Name English
NSC-402815
Code English
MONOCILLIN
Common Name English
BENZYLPENICILLIN SODIUM [WHO-IP]
Common Name English
PENICILLIN G SODIUM [ORANGE BOOK]
Common Name English
SODIUM (2S-(2.ALPHA.,5.ALPHA.,6.BETA.))-3,3-DIMETHYL-7-OXO-6-(PHENYLACETAMIDO)-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLATE
Common Name English
PENICILLIN G SODIUM [USP-RS]
Common Name English
Monosodium (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Systematic Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-6-(2-PHENYLACETAMIDO)-, MONOSODIUM SALT
Common Name English
BENZYL PENICILLIN SODIUM
Common Name English
PENICILLIN G SODIUM [USP MONOGRAPH]
Common Name English
ETHACILLIN
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3-DIMETHYL-7-OXO-6-((PHENYLACETYL)AMINO)-(2S,5R,6R)-, MONOSODIUM SALT
Common Name English
PENICILLIN G SODIUM [VANDF]
Common Name English
PENICILLIN G SODIUM SALT [MI]
Common Name English
BENZYLPENICILLINUM NATRICUM [WHO-IP LATIN]
Common Name English
BENZYLPENICILLIN SODIUM [EP MONOGRAPH]
Common Name English
PENICILLINUM
HPUS  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
Code System Code Type Description
EVMPD
SUB13038MIG
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
PRIMARY
RXCUI
9900
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
PRIMARY RxNorm
WHO INTERNATIONAL PHARMACOPEIA
PENICILLIN G SODIUM
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
PRIMARY Description: A white or almost white, crystalline powder; odourless or with a faint characteristic odour. Solubility: Soluble in about 0.5 part of water; practically insoluble in ether R. Category: Antibiotic. Storage: Benzylpenicillin sodium should be kept in a tightly closed container, protected from light, and stored at a temperature notexceeding 25?C. Labelling: The designation sterile Benzylpenicillin sodium indicates that the substance complies with the additional requirementsfor sterile Benzylpenicillin sodium and may be used for parenteral administration or for other sterile applications. Additional information: Benzylpenicillin sodium is hygroscopic; it is readily decomposed by acid, alkalis and oxidizing agents.Even in the absence of light, Benzylpenicillin sodium is gradually degraded on exposure to a humid atmosphere, thedecomposition being faster at higher temperatures. Definition: Benzylpenicillin sodium contains not less than 96.0% and not more than 102.0% of C16H17N2NaO4S, calculated withreference to the dried substance.
ChEMBL
CHEMBL29
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
PRIMARY
MERCK INDEX
m8473
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
PRIMARY Merck Index
CAS
69-57-8
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
PRIMARY
PUBCHEM
23668834
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
PRIMARY
CHEBI
51765
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
PRIMARY
DRUG BANK
DBSALT000726
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
PRIMARY
FDA UNII
YS5LY7JF4N
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
PRIMARY
NSC
402815
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
PRIMARY
NCI_THESAURUS
C28865
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
PRIMARY
RS_ITEM_NUM
1502701
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
PRIMARY
DAILYMED
YS5LY7JF4N
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-710-2
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
PRIMARY
EPA CompTox
DTXSID6040581
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
PRIMARY
SMS_ID
100000091609
Created by admin on Fri Dec 15 15:12:39 GMT 2023 , Edited by admin on Fri Dec 15 15:12:39 GMT 2023
PRIMARY
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ACTIVE MOIETY
http://apps.who.int/phint/pdf/b/Jb.6.1.54.pdf