PENICILLIN G

First approved in 1943

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H18N2O4S
Molecular Weight	334.3918
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)[C@]([H])(C(=O)O)N2C(=O)[C@]([H])([C@@]2([H])S1)N=C(Cc3ccccc3)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

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 226 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3245263	Inhibitor 7701	Sepsis Anthrax Actinomycosis Botulism Diphtheria

Conditions

Condition	Modality	Targets	Highest Phase	Product
Sepsis 68 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/065068s013lbl.pdf	Curative	Bacterial penicillin-binding protein	Approved 7997	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 983145600000
Anthrax 12 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/065068s013lbl.pdf	Curative	Bacterial penicillin-binding protein	Approved 7997	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 983145600000
Actinomycosis 12 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/065068s013lbl.pdf	Curative	Bacterial penicillin-binding protein	Approved 7997	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 983145600000
Botulism 13 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/065068s013lbl.pdf	Primary	Bacterial penicillin-binding protein	Approved 7997	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 983145600000
Diphtheria 38 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/065068s013lbl.pdf	Primary	Bacterial penicillin-binding protein	Approved 7997	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 983145600000

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 613 OAT3 570 OATP1B1 698	OAT3 299 OATP1B1 353

Drug as perpetrator

Target	Modality	Activity
OATP1B1 713	inhibitor 2614 Sources: https://link.springer.com/article/10.1007/s11095-011-0564-9	no
OAT3 572	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/22273603/ Page: 6	yes [IC50 102 uM]
OATP1B3 622	inhibitor 2614 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 299	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/22273603/ Page: 4	yes
OATP1B1 353	substrate 2752 Sources: https://link.springer.com/article/10.1007/s11095-011-0564-9	yes

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P0036L4
1PlusChem LLC	1P007YCM
1PlusChem LLC	1P00IM0J
1PlusChem LLC	1P01CCQW
A2B Chem	AB47704
A2B Chem	AD70310
A2B Chem	AI67539
AA Blocks	AA00361O
AK Scientific	G722
AK Scientific	K162
AK Scientific	O634
AK Scientific	P691
AK Scientific	R967
AK Scientific	X2930
AbovChem LLC	HY-17591
Alfa Chemistry	219393
Alfa Chemistry	ACM6011398
Alfa Chemistry	ACM69578
Alfa Chemistry	ACM7177459
Alinda	IBS-E0003173
Angene	AGN-PC-0TW5UN
Apollo Scientific	BIP0142
AstaTech	C76205
BLDpharm	BD146920
BLDpharm	BD148735
BOC Sciences	113-98-4
BOC Sciences	1538-09-6
BOC Sciences	54-35-3
BOC Sciences	6011-39-8
BOC Sciences	61-33-6
BOC Sciences	69-57-8
BOC Sciences	7009-88-3
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BioBlocks	A1853/0078020
BioSynth	Q-200701
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Bosche Scientific	P2335
Bosche Scientific	P2412
Bosche Scientific	P2744
Chem Scene	CS-0092782
Chem Scene	CS-0099461
Chem-Impex International	2473
Chem-Impex International	756
ChemBridge	5215935
ChemDiv	0342-0049
ChemShuttle	141734
Compound Cloud	22502
Compound Cloud	23664709
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Compound Cloud	23724855
Compound Cloud	24892863
Compound Cloud	5904
Compound Cloud	656811
Enamine	EN300-295513
Enamine	EN300-52612
Fluorochem	492417
Fluorochem	492564
Hairui	HR100356
Hairui	HR122813
Hairui	HR131823
Hairui	HR135599
Hairui	HR137961
Hangzhou APIChem Technology	AC-13297
Hangzhou APIChem Technology	AC-13436
Hangzhou APIChem Technology	AC-14408
Hangzhou Yuhao Chemical Technology	XJ5416
IBScreen	Bio-0602
Innovapharm	BBV-00048183
KeyOrganics	AS-15252
KeyOrganics	AS-75133
Lab Network	163
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Lab Network	LN01342245
Lab Network	LN01343666
Lab Network	LN01343834
Lab Network	LN03028742
Lab Seeker	SC-16403
Lab Seeker	SC-58301
Life Chemicals	F0001-2583
MedChem Express	HY-N7120
MedChem Express	HY-N7139B
MolMall	20757
MolPort	MolPort-001-946-859
MolPort	MolPort-002-136-722
MolPort	MolPort-003-666-255
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MolPort	MolPort-004-952-399
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MolPort	MolPort-019-998-469
MolPort	MolPort-046-701-783
Molnova	M10491
Molnova	M15662
Molnova	M18770
MuseChem	M046439
MuseChem	R000864
MuseChem	R001177
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MuseChem	R061327
NCI Plated 2007	117522
NCI Plated 2007	11941
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NCI Plated 2007	11944
NCI Plated 2007	11951
NCI Plated 2007	11964
NCI Plated 2007	131815
NCI Plated 2007	65897
Norris Pharm	NSZB-A133530
Princeton BioMolecular Research	OSSK_572995
Princeton BioMolecular Research	OSSL_858046
Ryan Scientific	L-Hyoscyamine
Selleck Chemicals	S4160
Selleck Chemicals	S5206
Selleck Chemicals	S5515
Selleck Chemicals	S5736
ShangHai Biochempartner	BCP14289
ShangHai Biochempartner	BCP19762
Sigma Aldrich	13752
Sigma Aldrich	13752\|SIGMA
Sigma Aldrich	1502508
Sigma Aldrich	1502508\|USP
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Sigma Aldrich	1502701\|USP
Sigma Aldrich	31735
Sigma Aldrich	31735\|SIAL
Sigma Aldrich	46609
Sigma Aldrich	46609\|SIAL
Sigma Aldrich	B0700000
Sigma Aldrich	B0700000\|SIAL
Sigma Aldrich	B0900000
Sigma Aldrich	B0900000\|SIAL
Sigma Aldrich	CDS020801
Sigma Aldrich	CDS020801\|ALDRICH
Sigma Aldrich	P3032
Sigma Aldrich	P3032\|SIGMA
Sigma Aldrich	P4687
Sigma Aldrich	P4687\|SIGMA
Sigma Aldrich	P7794
Sigma Aldrich	P7794\|SIGMA
Sigma Aldrich	P8721
Sigma Aldrich	P8721\|SIAL
Sigma Aldrich	PENK
Sigma Aldrich	PENK\|SIGMA
Sigma Aldrich	PENNA
Sigma Aldrich	PENNA\|SIGMA
Sigma Aldrich	PENP
Sigma Aldrich	PENP\|SIGMA
StruChem	SC-16403
StruChem	SC-58301
TargetMol	T0958
TargetMol	T4553
TargetMol	T5602
Tetrahedron	TS66202
Tetrahedron	TS78124
Tetrahedron	TS80075
TimTec	ST024776
TimTec	ST4040472
TimTec	ST51052951
TimTec	ST51240781
Toronto Research Chemicals	B288601
Toronto Research Chemicals	P223400
Toronto Research Chemicals	P223518
Toronto Research Chemicals	P755200
Vitas-M Laboratory	STK177194
Vitas-M Laboratory	STL453455
W&J PharmaChem	100997
Wonderchem	WD059S5
ZINC	ZINC000003871701	http://zinc15.docking.org/substances/ZINC000003871701
eMolecules	109703558
eMolecules	1276516
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mcule	MCULE-3293179256
mcule	MCULE-3899419884
mcule	MCULE-3955575945
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mcule	MCULE-6846784607
mcule	MCULE-7644229995
mcule	MCULE-7708800117
mcule	MCULE-8147252616

PubMed

Title	Date	PubMed
[Penicillin induced haemolytic anaemia. Communication of a case (author's transl)].	1975	1198282
Selection of metalloenzymes by catalytic activity using phage display and catalytic elution.	2001 Apr 2	11828452
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
[The use of veterinary drugs during pregnancy of the dog].	2001 Nov 15	11758478
[Treatment of acute bacterial meningitis].	2001 Nov 20	11826463
[Allergic alteration of leukocytes in patients with drug intolerance].	2001 Sep-Oct	11871304
Marked differences in antibiotic use and resistance between university hospitals in Vilnius, Lithuania, and Huddinge, Sweden.	2001 Winter	11822778
[Benzylpenicillin efficacy for neutropenic infection prophylaxis in patients with cancer and postcytostatic neutropenia].	2002	12516191
Treatment of amatoxin poisoning: 20-year retrospective analysis.	2002	12475187
Antibiotics differ in their tendency to cause infusion phlebitis: a prospective observational study.	2002	12195877
Treatment of latent syphilis in HIV-infected patients with 10 d of benzylpenicillin G benethamine: a prospective study in Maputo, Mozambique.	2002	12064687
[Difficulties with using T lymphocyte culture as a method for diagnosing allergies to benzylpenicillin].	2002	12043320
Gateways to Clinical Trials.	2002 Apr	12087878
[The Pneumococcal Observatory for the Central Region, 1 April 1999 to 31 March 2000].	2002 Apr	11980331
3: Community-acquired pneumonia.	2002 Apr 1	12013330
Immunoglobulin E binding determinants on beta-lactam drugs.	2002 Aug	12130943
Amoxicillin-induced exanthema in young adults with infectious mononucleosis: demonstration of drug-specific lymphocyte reactivity.	2002 Dec	12452866
Cysteine is exported from the Escherichia coli cytoplasm by CydDC, an ATP-binding cassette-type transporter required for cytochrome assembly.	2002 Dec 20	12393891
[Post-marketing surveillance of antibacterial activities of cefozopran against various clinical isolates--I. Gram-positive bacteria].	2002 Feb	11977919
Controlled administration of penicillin to patients with a positive history but negative skin and specific serum IgE tests.	2002 Feb	11929493
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
The 2.4-A crystal structure of the penicillin-resistant penicillin-binding protein PBP5fm from Enterococcus faecium in complex with benzylpenicillin.	2002 Jul	12222968
Liquid chromatographic determination of ampicillin residues in porcine muscle tissue by a multipenicillin analytical method: European Collaborative Study.	2002 Jul-Aug	12180684
Improved brain delivery of benzylpenicillin with a peptide-vector-mediated strategy.	2002 Jun	12164379
Primary (isolated) meningococcal pericarditis.	2002 Jun	12058796
Fatality after an injection of Bicillin into the tonsillar fossa during an adenotonsillectomy.	2002 Mar	11956542
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
Major role of organic anion transporter 3 in the transport of indoxyl sulfate in the kidney.	2002 May	11967025
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
Minimum inhibitory concentrations of 20 antimicrobial agents against Staphylococcus aureus isolated from bovine intramammary infections in Japan.	2002 Nov	12489715
Quality control of antibiotics before the implementation of an STD program in Northern Myanmar.	2002 Nov	12438896
Mechanism of the reduced elimination clearance of benzylpenicillin from cerebrospinal fluid in rats with intracisternal administration of lipopolysaccharide.	2002 Nov	12386127
Acyl-intermediate structures of the extended-spectrum class A beta-lactamase, Toho-1, in complex with cefotaxime, cephalothin, and benzylpenicillin.	2002 Nov 29	12221102
[Antimicrobial susceptibility of Streptococcus pneumoniae and Haemophilus influenzae isolated in major hospitals in Nagano Prefecture].	2002 Oct	12532636
Fatal outcome from meningococcal disease--an association with meningococcal phenotype but not with reduced susceptibility to benzylpenicillin.	2002 Oct	12435065
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	12358729
Modulation of GABA(A) receptor-mediated currents by benzophenone derivatives in isolated rat Purkinje neurones.	2002 Sep	12367621
Biochemical characterization of a novel extended-spectrum beta-lactamase from Pseudomonas aeruginosa 802.	2002 Spring	12002654
Benzylpenicillin differentially conjugates to IFN-gamma, TNF-alpha, IL-1beta, IL-4 and IL-13 but selectively reduces IFN-gamma activity.	2003 Feb	12562387
High-performance thin-layer chromatography-bioautography for multiple antibiotic residues in cow's milk.	2003 Feb 5	12505779
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

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.

Name

Type

Language

PENICILLIN G

Common Name

English

BENZYLPENICILLIN [INN]

Common Name

English

PENICILLIN G [MI]

Common Name

English

PHENOXYMETHYLPENICILLIN POTASSIUM IMPURITY A [EP]

Common Name

English

BENZYLPENICILLIN [WHO-DD]

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

PHENOXYMETHYLPENICILLIN IMPURITY A [EP]

Common Name

English

J01CE01

Code

English

BENZYLPENICILLIN

Official Name

English

NSC-193396

Code

English

BENZYL PENICILLIN

Common Name

English

PENICILLIN G [HSDB]

Common Name

English

BENZYLPENICILLIN [MART.]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000011281