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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+].CC1(C)S[C@@H]2[C@H](NC(=O)CC3=CC=CC=C3)C(=O)N2[C@H]1C([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 22.98976928
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
The optimization test in the guinea-pig. A method for the predictive evaluation of the contact allergenicity of chemicals.
1975 May
Penicillin-induced haemolytic anaemia associated with microangiopathy.
1976 Apr
Fresh vs aged benzylpenicillin on non-IgE responses in mice.
1998 Jan
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.
1999 May 7
Drug-induced hemolysis: cefotetan-dependent hemolytic anemia mimicking an acute intravascular immune transfusion reaction.
2000 May
[Severe community-acquired pneumonia: etiology].
2001
Optimisation of the prevention and treatment of bacterial endocarditis.
2001
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
Short-term effects of four antibiotics on DNA synthesis in endothelial cells.
2001 Apr
A theoretical study of the aminolysis reaction of lysine 199 of human serum albumin with benzylpenicillin: consequences for immunochemistry of penicillins.
2001 Aug 8
Degeneracy and additional alloreactivity of drug-specific human alpha beta(+) T cell clones.
2001 Jul
Benzylpenicillin-induced prolonged cholestasis.
2001 Jun
Purification and characterization of a beta-lactamase from Haemophilus ducreyi in Escherichia coli.
2001 Oct
Clinical evaluation of Pharmacia CAP System RAST FEIA amoxicilloyl and benzylpenicilloyl in patients with penicillin allergy.
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
Treatment of latent syphilis in HIV-infected patients with 10 d of benzylpenicillin G benethamine: a prospective study in Maputo, Mozambique.
2002
Immunoglobulin E binding determinants on beta-lactam drugs.
2002 Aug
[Post-marketing surveillance of antibacterial activities of cefozopran against various clinical isolates--I. Gram-positive bacteria].
2002 Feb
[Maximum residue levels (MRL's) of veterinary medicines in relation to food safety. MRL's really do matter--the Benzaprocpen case].
2002 Jan 1
Characterization of specific IgE response in vitro against protein and drug allergens using atopic and normal donors.
2002 Mar
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
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
[Antimicrobial susceptibility of Streptococcus pneumoniae and Haemophilus influenzae isolated in major hospitals in Nagano Prefecture].
2002 Oct
Benzylpenicillin differentially conjugates to IFN-gamma, TNF-alpha, IL-1beta, IL-4 and IL-13 but selectively reduces IFN-gamma activity.
2003 Feb
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 Mon Mar 31 17:50:18 GMT 2025
Edited
by admin
on Mon Mar 31 17:50:18 GMT 2025
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   MART.   WHO-DD   WHO-IP  
Preferred 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
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 Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
Code System Code Type Description
EVMPD
SUB13038MIG
Created by admin on Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
PRIMARY
RXCUI
9900
Created by admin on Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
PRIMARY RxNorm
WHO INTERNATIONAL PHARMACOPEIA
PENICILLIN G SODIUM
Created by admin on Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
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 Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
PRIMARY
MERCK INDEX
m8473
Created by admin on Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
PRIMARY Merck Index
CAS
69-57-8
Created by admin on Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
PRIMARY
PUBCHEM
23668834
Created by admin on Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
PRIMARY
CHEBI
51765
Created by admin on Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
PRIMARY
DRUG BANK
DBSALT000726
Created by admin on Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
PRIMARY
FDA UNII
YS5LY7JF4N
Created by admin on Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
PRIMARY
NSC
402815
Created by admin on Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
PRIMARY
NCI_THESAURUS
C28865
Created by admin on Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
PRIMARY
RS_ITEM_NUM
1502701
Created by admin on Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
PRIMARY
DAILYMED
YS5LY7JF4N
Created by admin on Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-710-2
Created by admin on Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
PRIMARY
EPA CompTox
DTXSID6040581
Created by admin on Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
PRIMARY
SMS_ID
100000091609
Created by admin on Mon Mar 31 17:50:18 GMT 2025 , Edited by admin on Mon Mar 31 17:50:18 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY
http://apps.who.int/phint/pdf/b/Jb.6.1.54.pdf