PENICILLIN G

First approved in 1943

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 Search

SMILES

CC1(C)S[C@@H]2[C@H](NC(=O)CC3=CC=CC=C3)C(=O)N2[C@H]1C(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

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
Penicillin and cephalosporin biosynthesis: mechanism of carbon catabolite regulation of penicillin production.	1999 Jan-Feb	10422579
Successful shortening from seven to four days of parenteral beta-lactam treatment for common childhood infections: a prospective and randomized study.	2001	11285152
Substrate binding and catalytic mechanism of class B beta-lactamases: a molecular modelling study.	2001 Dec	11814063
Gradient diffusion antibiotic susceptibility testing of potentially probiotic lactobacilli.	2001 Dec	11770631
[Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine].	2001 Feb	11265221
[CBO-guideline 'Bacterial meningitis'].	2001 Feb 3	11219147
Insights into the molecular basis for the carbenicillinase activity of PSE-4 beta-lactamase from crystallographic and kinetic studies.	2001 Jan 16	11148033
Molecular dynamics study of the IIA binding site in human serum albumin: influence of the protonation state of Lys195 and Lys199.	2001 Jan 18	11170635
[Hoigne syndrome as an acute non-allergic reaction to different drugs: case reports].	2001 Jun	11503262
Antimicrobial susceptibilities of Erysipelothrix rhusiopathiae isolated from pigs with swine erysipelas in Japan, 1988-1998.	2001 Mar	11315521
Interaction of 2,3-dimercapto-1-propane sulfonate with the human organic anion transporter hOAT1.	2001 Nov	11602689
[The use of veterinary drugs during pregnancy of the dog].	2001 Nov 15	11758478
[Allergic alteration of leukocytes in patients with drug intolerance].	2001 Sep-Oct	11871304
Treatment of amatoxin poisoning: 20-year retrospective analysis.	2002	12475187
Amoxicillin-induced exanthema in young adults with infectious mononucleosis: demonstration of drug-specific lymphocyte reactivity.	2002 Dec	12452866
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	11802794
Chloramphenicol versus benzylpenicillin and gentamicin for the treatment of severe pneumonia in children in Papua New Guinea: a randomised trial.	2002 Feb 9	11853793
Comparative in vitro activity of 16 antimicrobial agents against Actinobacillus pleuropneumoniae.	2002 Jan	11860083
Natural antibiotic susceptibility and biochemical profiles of Yersinia enterocolitica-like strains: Y. bercovieri, Y. mollaretii, Y. aldovae and 'Y. ruckeri'.	2002 Jan	11800473
[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
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
Quality control of antibiotics before the implementation of an STD program in Northern Myanmar.	2002 Nov	12438896
Fatal outcome from meningococcal disease--an association with meningococcal phenotype but not with reduced susceptibility to benzylpenicillin.	2002 Oct	12435065

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 17:33:15 GMT 2025` Edited by `admin` on `Mon Mar 31 17:33:15 GMT 2025`
Record UNII	Q42T66VG0C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENZYLPENICILLIN

Preferred Name

English

PENICILLIN G

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

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