PENICILLIN G SODIUM

First approved in 1943

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 Search

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

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/065068s013lbl.pdf |

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.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 234 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3245263	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Sepsis 74 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/065068s013lbl.pdf	Curative	Approved 8583	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
Anthrax 14 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/065068s013lbl.pdf	Curative	Approved 8583	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
Actinomycosis 14 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/065068s013lbl.pdf	Curative	Approved 8583	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
Botulism 15 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/065068s013lbl.pdf	Primary	Approved 8583	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
Diphtheria 40 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/065068s013lbl.pdf	Primary	Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
400 μg/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050638s019lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.1 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21991307/	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
65% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8218695/	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% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/050141s237lbl.pdf			PENICILLIN G serum	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B3 961 OAT3 747 OATP1B1 1079	OAT3 391 OATP1B1 503

Drug as perpetrator

Target	Modality	Activity
OATP1B1 1095	inhibitor 4027 Sources: https://link.springer.com/article/10.1007/s11095-011-0564-9	no
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22273603/ Page: 6.0	yes [IC50 102 uM]
OATP1B3 970	inhibitor 4027 Sources: https://academic.oup.com/toxsci/article/91/1/140/1672682	yes [IC50 25 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OAT3 391	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/22273603/ Page: 4.0	yes
OATP1B1 503	substrate 4014 Sources: https://link.springer.com/article/10.1007/s11095-011-0564-9	yes

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B1-01426	http://www.3bsc.com/index/pro_info.php?id=21638
3B Scientific (Wuhan) Corp	3B3-003867	http://www.3bsc.com/index/pro_info.php?id=25758
AHH Chemical co.,ltd	MT-58094	http://www.ahhchemical.com/product/MT-58094.html
Alfa Chemistry	ACM61336	https://www.alfa-chemistry.com/penicillin-g-cas-61-33-6-item-1451.htm
Aurora Fine Chemicals LLC	A13.126.111	http://online.aurorafinechemicals.com/info?ID=A13.126.111
Aurora Fine Chemicals LLC	K14.717.681	http://online.aurorafinechemicals.com/info?ID=K14.717.681
BioSynth	W-109262	https://www.biosynth.com/en/products/life-science/culture-media-additives/products/W-109262.html
BLD Pharm	BD16410	http://www.bldpharm.com/products/61-33-6.html
ChemMol	99117822	http://www.chemmol.com/chemmol/99117822.html
eNovation Chemicals	D670398	https://www.enovationchem.com/ProductDetails.asp?ProductID=D670398
Hairui	HR131823	http://www.hairuichem.com/en/product/113-98-4.html
iChemical	EBD2201844	http://www.ichemical.com/products/61-33-6.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
OChem	11946	http://www.ocheminc.com/index.php?act=psearch&pid=061P336
Smolecule	S520981	http://www.smolecule.com/products/s520981
Smolecule	S793352	https://www.smolecule.com/products/s793352
THE BioTek	bt-261722	https://www.thebiotek.com/product/inhibitors/bt-261722
THE BioTek	bt-318404	https://www.thebiotek.com/product/others/bt-318404
W&J PharmaChem	100997	http://www.wjpharmachem.com/new/100997.html

PubMed

Title	Date	PubMed
The optimization test in the guinea-pig. A method for the predictive evaluation of the contact allergenicity of chemicals.	1975 May	1155304
Penicillin-induced haemolytic anaemia associated with microangiopathy.	1976 Apr	1067815
Fresh vs aged benzylpenicillin on non-IgE responses in mice.	1998 Jan	10375765
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.	1999 May 7	10224140
Drug-induced hemolysis: cefotetan-dependent hemolytic anemia mimicking an acute intravascular immune transfusion reaction.	2000 May	10815791
[Severe community-acquired pneumonia: etiology].	2001	11573325
Optimisation of the prevention and treatment of bacterial endocarditis.	2001	11419916
Melatonin might be one possible medium of electroacupuncture anti-seizures.	2001	11394492
Encouraging good antimicrobial prescribing practice: a review of antibiotic prescribing policies used in the South East Region of England.	2001	11388888
Short-term effects of four antibiotics on DNA synthesis in endothelial cells.	2001 Apr	11322179
A theoretical study of the aminolysis reaction of lysine 199 of human serum albumin with benzylpenicillin: consequences for immunochemistry of penicillins.	2001 Aug 8	11480978
Degeneracy and additional alloreactivity of drug-specific human alpha beta(+) T cell clones.	2001 Jul	11431418
Benzylpenicillin-induced prolonged cholestasis.	2001 Jun	11409000
Purification and characterization of a beta-lactamase from Haemophilus ducreyi in Escherichia coli.	2001 Oct	11570857
Clinical evaluation of Pharmacia CAP System RAST FEIA amoxicilloyl and benzylpenicilloyl in patients with penicillin allergy.	2001 Sep	11551251
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	11535796
Inhibition of translocation of beta -lactamase into the yeast endoplasmic reticulum by covalently bound benzylpenicillin.	2001 Sep 14	11447216
[Allergic alteration of leukocytes in patients with drug intolerance].	2001 Sep-Oct	11871304
Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects.	2001 Sep-Oct	11746950
Treatment of latent syphilis in HIV-infected patients with 10 d of benzylpenicillin G benethamine: a prospective study in Maputo, Mozambique.	2002	12064687
Immunoglobulin E binding determinants on beta-lactam drugs.	2002 Aug	12130943
[Post-marketing surveillance of antibacterial activities of cefozopran against various clinical isolates--I. Gram-positive bacteria].	2002 Feb	11977919
[Maximum residue levels (MRL's) of veterinary medicines in relation to food safety. MRL's really do matter--the Benzaprocpen case].	2002 Jan 1	11795030
Characterization of specific IgE response in vitro against protein and drug allergens using atopic and normal donors.	2002 Mar	11906332
Evaluation of the new VITEK 2 system for determination of the susceptibility of clinical isolates of Streptococcus pneumoniae.	2002 Mar	11901253
Functional involvement of rat organic anion transporter 3 (rOat3; Slc22a8) in the renal uptake of organic anions.	2002 Mar	11861777
Expression and functional characterization of rat organic anion transporter 3 (rOat3) in the choroid plexus.	2002 May	11961115
[Use of antibiotics in general practice and at the Clinic for Infectious Diseases].	2002 May-Jun	12170869
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.	2002 Nov	12569987
[Antimicrobial susceptibility of Streptococcus pneumoniae and Haemophilus influenzae isolated in major hospitals in Nagano Prefecture].	2002 Oct	12532636
Benzylpenicillin differentially conjugates to IFN-gamma, TNF-alpha, IL-1beta, IL-4 and IL-13 but selectively reduces IFN-gamma activity.	2003 Feb	12562387
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	12526667

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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

Common Name

English

BENZYLPENICILLIN SODIUM

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

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

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1500