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

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC3=CC=CC=C3)C(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 233 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3245263	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Sepsis 71 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/065068s013lbl.pdf	Curative	Approved 8429	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 8429	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 8429	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 8429	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 8429	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 706 OAT3 642 OATP1B1 788	OAT3 339 OATP1B1 406

Drug as perpetrator

Target	Modality	Activity
OATP1B1 803	inhibitor 3277 Sources: https://link.springer.com/article/10.1007/s11095-011-0564-9	no
OAT3 644	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22273603/ Page: 6.0	yes [IC50 102 uM]
OATP1B3 715	inhibitor 3277 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 339	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/22273603/ Page: 4.0	yes
OATP1B1 406	substrate 3367 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
BLD Pharm	BD16410	http://www.bldpharm.com/products/61-33-6.html
BioSynth	W-109262	https://www.biosynth.com/en/products/life-science/culture-media-additives/products/W-109262.html
ChemMol	99117822	http://www.chemmol.com/chemmol/99117822.html
Hairui	HR131823	http://www.hairuichem.com/en/product/113-98-4.html
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
eNovation Chemicals	D670398	https://www.enovationchem.com/ProductDetails.asp?ProductID=D670398
iChemical	EBD2201844	http://www.ichemical.com/products/61-33-6.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
[Penicillin induced haemolytic anaemia. Communication of a case (author's transl)].	1975	1198282
Anaphylaxis manifested by hypotension alone.	1975 Jan	1113380
The optimization test in the guinea-pig. A method for the predictive evaluation of the contact allergenicity of chemicals.	1975 May	1155304
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
Dual inhibitory activity of sitafloxacin (DU-6859a) against DNA gyrase and topoisomerase IV of Streptococcus pneumoniae.	1999 Oct	10588315
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
Encouraging good antimicrobial prescribing practice: a review of antibiotic prescribing policies used in the South East Region of England.	2001	11388888
Successful shortening from seven to four days of parenteral beta-lactam treatment for common childhood infections: a prospective and randomized study.	2001	11285152
[Epidemiological survey for hemolytic streptococci isolated from children in Tokyo].	2001 Apr	11357322
Selection of metalloenzymes by catalytic activity using phage display and catalytic elution.	2001 Apr 2	11828452
Novel periodontal drug delivery system for treatment of periodontitis.	2001 Apr 28	11295218
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
Gradient diffusion antibiotic susceptibility testing of potentially probiotic lactobacilli.	2001 Dec	11770631
Natural antibiotic susceptibility of strains of the Enterobacter cloacae complex.	2001 Dec	11738341
[Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine].	2001 Feb	11265221
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
Degeneracy and additional alloreactivity of drug-specific human alpha beta(+) T cell clones.	2001 Jul	11431418
Epidemiology and diagnosis of meningitis: results of a five-year prospective, population-based study.	2001 Jun	11525000
[Hoigne syndrome as an acute non-allergic reaction to different drugs: case reports].	2001 Jun	11503262
Benzylpenicillin-induced prolonged cholestasis.	2001 Jun	11409000
[Cellulitis and necrotizing fasciitis: microbiology and pathogenesis].	2001 Mar	11319369
Comparative study of treatment with penicillin, ceftriaxone, trovafloxacin, quinupristin-dalfopristin and vancomycin in experimental endocarditis due to penicillin- and ceftriaxone-resistant Streptococcus pneumoniae.	2001 May	11328774
Reaction of Lys-Tyr-Lys triad mimics with benzylpenicillin: insight into the role of Tyr150 in class C beta-lactamase.	2001 May 7	11354367
[Treatment of acute bacterial meningitis].	2001 Nov 20	11826463
Purification and characterization of a beta-lactamase from Haemophilus ducreyi in Escherichia coli.	2001 Oct	11570857
Tetracycline-resistance genes of Clostridium perfringens, Clostridium septicum and Clostridium sordellii isolated from cattle affected with malignant edema.	2001 Oct 22	11524166
Clinical evaluation of Pharmacia CAP System RAST FEIA amoxicilloyl and benzylpenicilloyl in patients with penicillin allergy.	2001 Sep	11551251
3: Community-acquired pneumonia.	2002 Apr 1	12013330
Cysteine is exported from the Escherichia coli cytoplasm by CydDC, an ATP-binding cassette-type transporter required for cytochrome assembly.	2002 Dec 20	12393891
Chloramphenicol versus benzylpenicillin and gentamicin for the treatment of severe pneumonia in children in Papua New Guinea: a randomised trial.	2002 Feb 9	11853793
Natural antibiotic susceptibility and biochemical profiles of Yersinia enterocolitica-like strains: Y. bercovieri, Y. mollaretii, Y. aldovae and 'Y. ruckeri'.	2002 Jan	11800473
Liquid chromatographic determination of ampicillin residues in porcine muscle tissue by a multipenicillin analytical method: European Collaborative Study.	2002 Jul-Aug	12180684
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
Expression and functional characterization of rat organic anion transporter 3 (rOat3) in the choroid plexus.	2002 May	11961115
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
Acyl-intermediate structures of the extended-spectrum class A beta-lactamase, Toho-1, in complex with cefotaxime, cephalothin, and benzylpenicillin.	2002 Nov 29	12221102
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 `Fri Dec 15 14:58:04 GMT 2023` Edited by `admin` on `Fri Dec 15 14:58:04 GMT 2023`
Record UNII	Q42T66VG0C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

BENZYLPENICILLIN

Official Name

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