PENICILLIN G PROCAINE

First approved in 1943

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H18N2O4S.C13H20N2O2.H2O
Molecular Weight	588.716
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.[H][C@]23SC(C)(C)[C@@H](N2C(=O)[C@H]3NC(=O)CC4=CC=CC=C4)C(O)=O

InChI

InChIKey=KZDCMKVLEYCGQX-UDPGNSCCSA-N

InChI=1S/C16H18N2O4S.C13H20N2O2.H2O/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;1-3-15(4-2)9-10-17-13(16)11-5-7-12(14)8-6-11;/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);5-8H,3-4,9-10,14H2,1-2H3;1H2/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

Molecular Formula	C13H20N2O2
Molecular Weight	236.3101
Charge	0
Count

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

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

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
Penicillin-induced immune hemolytic anemia. Occurrence of massive intravascular hemolysis.	1975 Aug 4	1173853
The optimization test in the guinea-pig. A method for the predictive evaluation of the contact allergenicity of chemicals.	1975 May	1155304
Routine prophylactic antibiotic use in the management of snakebite.	2001	11710972
[Severe community-acquired pneumonia: etiology].	2001	11573325
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
False penicillin resistance in Neisseria meningitidis following direct susceptibility tests from blood cultures.	2001 Nov	11684730
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
[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
Antibiotic usage in Nordic countries.	2001 Sep	11673043
Determination of benzylpenicillin, oxacillin, cloxacillin, and dicloxacillin in cows' milk by ion-pair high-performance liquid chromatography after precolumn derivatization.	2001 Sep	11605761
Diagnostic evaluation of a large group of patients with immediate allergy to penicillins: the role of skin testing.	2001 Sep	11551249
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
Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects.	2001 Sep-Oct	11746950
[Benzylpenicillin efficacy for neutropenic infection prophylaxis in patients with cancer and postcytostatic neutropenia].	2002	12516191
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
Gateways to Clinical Trials.	2002 Apr	12087878
[The Pneumococcal Observatory for the Central Region, 1 April 1999 to 31 March 2000].	2002 Apr	11980331
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
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
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
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
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
[Antimicrobial susceptibility of Streptococcus pneumoniae and Haemophilus influenzae isolated in major hospitals in Nagano Prefecture].	2002 Oct	12532636
Biochemical characterization of a novel extended-spectrum beta-lactamase from Pseudomonas aeruginosa 802.	2002 Spring	12002654
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 `Fri Dec 15 16:16:27 GMT 2023` Edited by `admin` on `Fri Dec 15 16:16:27 GMT 2023`
Record UNII	17R794ESYN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PENICILLIN G PROCAINE

Common Name

English

Procaine benzylpenicillin [WHO-DD]

Common Name

English

BENZYLPENICILLIN PROCAINE

Common Name

English

PENICILLIN G PROCAINE [VANDF]

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)-, COMPD. WITH 2-(DIETHYLAMINO)ETHYL 4-AMINOBENZOATE, HYDRATE (1:1:1)

Common Name

English

DURACILLIN A.S.

Brand Name

English

BICILLIN C-R COMPONENT PENICILLIN G PROCAINE

Common Name

English

PROCAINE BENZYLPENICILLIN

Common Name

English

PROCAINI BENZYLPENICILLINUM [WHO-IP LATIN]

Common Name

English

PROCAINE PENICILLIN G MONOHYDRATE

Common Name

English

PENICILLIN G PROCAINE [USP MONOGRAPH]

Common Name

English

PENICILLIN G PROCAINE COMPONENT OF BICILLIN C-R

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.))-, COMPD. WITH 2-(DIETHYLAMINO)ETHYL 4-AMINOBENZOATE (1:1) MONOHYDRATE

Common Name

English

PENICILLIN G PROCAINE [USP-RS]

Common Name

English

PROCAINE PENICILLIN G

Common Name

English

PROCAINE BENZYLPENICILLIN [WHO-IP]

Common Name

English

CRYSTICILLIN A.S.

Brand Name

English

PENICILLIN G PROCAINE [ORANGE BOOK]

Common Name

English

PFIZERPEN-AS

Brand Name

English

PENICILLIN G PROCAINE [MI]

Common Name

English

PENICILLIN G PROCAINE [GREEN BOOK]

Common Name

English

PROCAINE PENICILLIN

Common Name

English

PROCAINE BENZYLPENICILLIN [MART.]

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 2-(DIETHYLAMINO)ETHYL P-AMINOBENZOATE (1:1) MONOHYDRATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1500