U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of PENICILLIN G

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

PubMed

PubMed

TitleDatePubMed
Penicillin-induced immune hemolytic anemia. Occurrence of massive intravascular hemolysis.
1975 Aug 4
Routine prophylactic antibiotic use in the management of snakebite.
2001
[Severe community-acquired pneumonia: etiology].
2001
Optimisation of the prevention and treatment of bacterial endocarditis.
2001
Melatonin might be one possible medium of electroacupuncture anti-seizures.
2001
Encouraging good antimicrobial prescribing practice: a review of antibiotic prescribing policies used in the South East Region of England.
2001
Successful shortening from seven to four days of parenteral beta-lactam treatment for common childhood infections: a prospective and randomized study.
2001
[Epidemiological survey for hemolytic streptococci isolated from children in Tokyo].
2001 Apr
Short-term effects of four antibiotics on DNA synthesis in endothelial cells.
2001 Apr
Selection of metalloenzymes by catalytic activity using phage display and catalytic elution.
2001 Apr 2
A theoretical study of the aminolysis reaction of lysine 199 of human serum albumin with benzylpenicillin: consequences for immunochemistry of penicillins.
2001 Aug 8
Gradient diffusion antibiotic susceptibility testing of potentially probiotic lactobacilli.
2001 Dec
Natural antibiotic susceptibility of strains of the Enterobacter cloacae complex.
2001 Dec
[Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine].
2001 Feb
Structures of the acyl-enzyme complexes of the Staphylococcus aureus beta-lactamase mutant Glu166Asp:Asn170Gln with benzylpenicillin and cephaloridine.
2001 Feb 27
[CBO-guideline 'Bacterial meningitis'].
2001 Feb 3
Epidemiology and diagnosis of meningitis: results of a five-year prospective, population-based study.
2001 Jun
Benzylpenicillin-induced prolonged cholestasis.
2001 Jun
[Cellulitis and necrotizing fasciitis: microbiology and pathogenesis].
2001 Mar
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
Reaction of Lys-Tyr-Lys triad mimics with benzylpenicillin: insight into the role of Tyr150 in class C beta-lactamase.
2001 May 7
False penicillin resistance in Neisseria meningitidis following direct susceptibility tests from blood cultures.
2001 Nov
[The use of veterinary drugs during pregnancy of the dog].
2001 Nov 15
[Treatment of acute bacterial meningitis].
2001 Nov 20
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
Tetracycline-resistance genes of Clostridium perfringens, Clostridium septicum and Clostridium sordellii isolated from cattle affected with malignant edema.
2001 Oct 22
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
Inhibition of translocation of beta -lactamase into the yeast endoplasmic reticulum by covalently bound benzylpenicillin.
2001 Sep 14
[Allergic alteration of leukocytes in patients with drug intolerance].
2001 Sep-Oct
Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects.
2001 Sep-Oct
[Benzylpenicillin efficacy for neutropenic infection prophylaxis in patients with cancer and postcytostatic neutropenia].
2002
[Difficulties with using T lymphocyte culture as a method for diagnosing allergies to benzylpenicillin].
2002
Gateways to Clinical Trials.
2002 Apr
3: Community-acquired pneumonia.
2002 Apr 1
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
Chloramphenicol versus benzylpenicillin and gentamicin for the treatment of severe pneumonia in children in Papua New Guinea: a randomised trial.
2002 Feb 9
Comparative in vitro activity of 16 antimicrobial agents against Actinobacillus pleuropneumoniae.
2002 Jan
Natural antibiotic susceptibility and biochemical profiles of Yersinia enterocolitica-like strains: Y. bercovieri, Y. mollaretii, Y. aldovae and 'Y. ruckeri'.
2002 Jan
[Maximum residue levels (MRL's) of veterinary medicines in relation to food safety. MRL's really do matter--the Benzaprocpen case].
2002 Jan 1
Primary (isolated) meningococcal pericarditis.
2002 Jun
Fatality after an injection of Bicillin into the tonsillar fossa during an adenotonsillectomy.
2002 Mar
Characterization of specific IgE response in vitro against protein and drug allergens using atopic and normal donors.
2002 Mar
Evaluation of the new VITEK 2 system for determination of the susceptibility of clinical isolates of Streptococcus pneumoniae.
2002 Mar
Functional involvement of rat organic anion transporter 3 (rOat3; Slc22a8) in the renal uptake of organic anions.
2002 Mar
Major role of organic anion transporter 3 in the transport of indoxyl sulfate in the kidney.
2002 May
[Use of antibiotics in general practice and at the Clinic for Infectious Diseases].
2002 May-Jun
Quality control of antibiotics before the implementation of an STD program in Northern Myanmar.
2002 Nov
Fatal outcome from meningococcal disease--an association with meningococcal phenotype but not with reduced susceptibility to benzylpenicillin.
2002 Oct
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
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
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
HSDB   MI   VANDF  
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
INN   MART.   WHO-DD  
INN  
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
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
NDF-RT N0000011281
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
NCI_THESAURUS C1500
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
NDF-RT N0000011281
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
LIVERTOX 753
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
FDA ORPHAN DRUG 37689
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
WHO-ATC J01CE01
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
WHO-VATC QS01AA14
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
WHO-ATC J01CE09
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
WHO-VATC QJ51CE01
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
CFR 21 CFR 520.1696B
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
NDF-RT N0000011281
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
NDF-RT N0000175497
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
WHO-VATC QJ01CE01
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
FDA ORPHAN DRUG 18787
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
WHO-VATC QJ51RC22
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
NDF-RT N0000011281
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
NDF-RT N0000011281
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
NDF-RT N0000011281
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.1
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
NDF-RT N0000011281
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
WHO-ATC S01AA14
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
NDF-RT N0000011281
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
WHO-VATC QG51AG02
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL29
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-506-3
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
PRIMARY
MESH
D010400
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
PRIMARY
CAS
61-33-6
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
PRIMARY
WIKIPEDIA
BENZYLPENICILLIN
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
PRIMARY
IUPHAR
4796
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
PRIMARY
NCI_THESAURUS
C61883
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
PRIMARY
EVMPD
SUB05772MIG
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
PRIMARY
DRUG BANK
DB01053
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
PRIMARY
MERCK INDEX
M8473
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
PRIMARY Merck Index
LactMed
61-33-6
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
PRIMARY
INN
58
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
PRIMARY
EPA CompTox
61-33-6
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
PRIMARY
PUBCHEM
5904
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
PRIMARY
HSDB
61-33-6
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
PRIMARY
RXCUI
7980
Created by admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
PRIMARY RxNorm