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

Description

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 223	Inhibitor 7468	Actinomycosis

Conditions

Condition	Modality	Targets	Highest Phase	Product
Septicemia 37	Primary	Bacterial penicillin-binding protein	Approved 7883	PENICILLIN G SODIUM
Anthrax 12	Primary	Bacterial penicillin-binding protein	Approved 7883	PENICILLIN G SODIUM
Diphtheria 40	Primary	Bacterial penicillin-binding protein	Approved 7883	PENICILLIN G SODIUM
Actinomycosis 12	Primary	Bacterial penicillin-binding protein	Approved 7883	PENICILLIN G SODIUM
Botulism 13	Primary	Bacterial penicillin-binding protein	Approved 7883	PENICILLIN G SODIUM
[Community-acquired pneumonia (children), Cutibacterium acnes infection of deep-brain stimulation hardware, Group B streptococcus (maternal dose (neonatal prophylaxis)), Leptospirosis, Lyme neuroborreliosis, Osteomyelitis, native vertebral, Prosthetic joint infection, Skin and soft tissue infections, Whipple Disease] 12			Approved (off-label) 8

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
[Severe community-acquired pneumonia: etiology].	2001	11573325
Optimisation of the prevention and treatment of bacterial endocarditis.	2001	11419916
Melatonin might be one possible medium of electroacupuncture anti-seizures.	2001	11394492
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
Short-term effects of four antibiotics on DNA synthesis in endothelial cells.	2001 Apr	11322179
Selection of metalloenzymes by catalytic activity using phage display and catalytic elution.	2001 Apr 2	11828452
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
Structures of the acyl-enzyme complexes of the Staphylococcus aureus beta-lactamase mutant Glu166Asp:Asn170Gln with benzylpenicillin and cephaloridine.	2001 Feb 27	11327855
[CBO-guideline 'Bacterial meningitis'].	2001 Feb 3	11219147
Epidemiology and diagnosis of meningitis: results of a five-year prospective, population-based study.	2001 Jun	11525000
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
False penicillin resistance in Neisseria meningitidis following direct susceptibility tests from blood cultures.	2001 Nov	11684730
[The use of veterinary drugs during pregnancy of the dog].	2001 Nov 15	11758478
[Treatment of acute bacterial meningitis].	2001 Nov 20	11826463
Molecular dynamics simulations of the mononuclear zinc-beta-lactamase from Bacillus cereus complexed with benzylpenicillin and a quantum chemical study of the reaction mechanism.	2001 Oct 10	11583551
Tetracycline-resistance genes of Clostridium perfringens, Clostridium septicum and Clostridium sordellii isolated from cattle affected with malignant edema.	2001 Oct 22	11524166
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
Inhibition of translocation of beta -lactamase into the yeast endoplasmic reticulum by covalently bound benzylpenicillin.	2001 Sep 14	11447216
[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
[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
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
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
[Use of antibiotics in general practice and at the Clinic for Infectious Diseases].	2002 May-Jun	12170869
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
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
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 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: intravenously; intramuscularly

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