PENICILLIN G BENZATHINE

First approved in 1943

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H20N2.2C16H18N2O4S.4H2O
Molecular Weight	981.185
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.O.O.O.C(CNCC1=CC=CC=C1)NCC2=CC=CC=C2.[H][C@]34SC(C)(C)[C@@H](N3C(=O)[C@H]4NC(=O)CC5=CC=CC=C5)C(O)=O.[H][C@]67SC(C)(C)[C@@H](N6C(=O)[C@H]7NC(=O)CC8=CC=CC=C8)C(O)=O

InChI

InChIKey=WIDKTXGNSOORHA-CJHXQPGBSA-N

InChI=1S/2C16H18N2O4S.C16H20N2.4H2O/c2*1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9;1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16;;;;/h2*3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);1-10,17-18H,11-14H2;4*1H2/t2*11-,12+,14-;;;;;/m11...../s1

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C16H20N2
Molecular Weight	240.3434
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 232 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3245263	Inhibitor 8228

Conditions

Condition	Modality	Highest Phase	Product
Sepsis 71 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/065068s013lbl.pdf	Curative	Approved 8360	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 9.8314558E11
Anthrax 14 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/065068s013lbl.pdf	Curative	Approved 8360	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 9.8314558E11
Actinomycosis 14 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/065068s013lbl.pdf	Curative	Approved 8360	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 9.8314558E11
Botulism 15 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/065068s013lbl.pdf	Primary	Approved 8360	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 9.8314558E11
Diphtheria 40 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/065068s013lbl.pdf	Primary	Approved 8360	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 9.8314558E11

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 700 OAT3 636 OATP1B1 781	OAT3 333 OATP1B1 403

Drug as perpetrator

Target	Modality	Activity
OATP1B1 796	inhibitor 3240 Sources: https://link.springer.com/article/10.1007/s11095-011-0564-9	no
OAT3 638	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/22273603/ Page: 6.0	yes [IC50 102 uM]
OATP1B3 709	inhibitor 3240 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 333	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/22273603/ Page: 4.0	yes
OATP1B1 403	substrate 3326 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 immune hemolytic anemia. Occurrence of massive intravascular hemolysis.	1975 Aug 4	1173853
Routine prophylactic antibiotic use in the management of snakebite.	2001	11710972
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
Natural antibiotic susceptibility of strains of the Enterobacter cloacae complex.	2001 Dec	11738341
[In vitro and in vivo activities of panipenem against penicillin-resistant Streptococcus pneumoniae].	2001 Jul	11560055
Epidemiology and diagnosis of meningitis: results of a five-year prospective, population-based study.	2001 Jun	11525000
[Allergy to penicillin: facts and controversies].	2001 Jun	11503267
[Hoigne syndrome as an acute non-allergic reaction to different drugs: case reports].	2001 Jun	11503262
Contribution of alveolar phagocytes to antibiotic efficacy in an experimental lung infection with Streptococcus pneumoniae.	2001 May	11545565
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
Antibiotic usage in Nordic countries.	2001 Sep	11673043
Diagnostic evaluation of a large group of patients with immediate allergy to penicillins: the role of skin testing.	2001 Sep	11551249
The VanY(D) DD-carboxypeptidase of Enterococcus faecium BM4339 is a penicillin-binding protein.	2001 Sep	11535797
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
[Allergic alteration of leukocytes in patients with drug intolerance].	2001 Sep-Oct	11871304
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
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
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
[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
Evaluation of the new VITEK 2 system for determination of the susceptibility of clinical isolates of Streptococcus pneumoniae.	2002 Mar	11901253
Major role of organic anion transporter 3 in the transport of indoxyl sulfate in the kidney.	2002 May	11967025
[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
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

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 `Wed Jul 05 22:31:12 UTC 2023` Edited by `admin` on `Wed Jul 05 22:31:12 UTC 2023`
Record UNII	RIT82F58GK
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PENICILLIN G BENZATHINE

Common Name

English

PENICILLIN G BENZATHINE [GREEN BOOK]

Common Name

English

BENZATHINE BENZYLPENICILLIN [MART.]

Common Name

English

BENZATHINE BENZYLPENICILLIN

Common Name

English

PENICILLIN G BENZATHINE [USP-RS]

Common Name

English

BENZATHINE BENZYLPENICILLIN TETRAHYDRATE

Common Name

English

BENZATHINE PENICILLIN

Common Name

English

PERMAPEN

Brand Name

English

PENICILLIN G BENZATHINE [USP MONOGRAPH]

Common Name

English

BENZYLPENICILLIN BENZATHINE

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 COMPOUND WITH N,N'-DIBENZYLETHYLENEDIAMINE (2:1), TETRAHYDRATE

Common Name

English

PENICILLIN G BENZATHINE [USP IMPURITY]

Common Name

English

BICILLIN C-R COMPONENT PENICILLIN G BENZATHINE

Common Name

English

BENZYLPENICILLIN BENZATHINE HYDRATE [JAN]

Common Name

English

PENICILLIN G BENZATHINE COMPONENT OF BICILLIN C-R

Common Name

English

BENZYLPENICILLIN BENZATHINE HYDRATE

Common Name

English

PENICILLIN G BENZATHINE [VANDF]

Common Name

English

PENICILLIN G BENZATHINE [ORANGE BOOK]

Common Name

English

PENICILLIN G BENZATHINE [MI]

Common Name

English

BICILLIN

Brand 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.))-, COMPD. WITH N,N'-BIS(PHENYLMETHYL)-1,2-ETHANEDIAMINE (2:1), TETRAHYDRATE

Common Name

English

Classification Tree Code System Code

WHO-ESSENTIAL MEDICINES LIST

6.2.1