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

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H20N2.2C16H18N2O4S
Molecular Weight 909.124
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENICILLIN G BENZATHINE ANHYDROUS

SMILES

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=BVGLIYRKPOITBQ-ANPZCEIESA-N
InChI=1S/2C16H18N2O4S.C16H20N2/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/t2*11-,12+,14-;/m11./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 C16H20N2
Molecular Weight 240.3434
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
Curative
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
Curative
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
Primary
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
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
400 μg/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.1 day
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
65%
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%
PENICILLIN G serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Penicillin-induced immune hemolytic anemia. Occurrence of massive intravascular hemolysis.
1975 Aug 4
The optimization test in the guinea-pig. A method for the predictive evaluation of the contact allergenicity of chemicals.
1975 May
Routine prophylactic antibiotic use in the management of snakebite.
2001
[Severe community-acquired pneumonia: etiology].
2001
Gradient diffusion antibiotic susceptibility testing of potentially probiotic lactobacilli.
2001 Dec
[In vitro and in vivo activities of panipenem against penicillin-resistant Streptococcus pneumoniae].
2001 Jul
Epidemiology and diagnosis of meningitis: results of a five-year prospective, population-based study.
2001 Jun
[The use of veterinary drugs during pregnancy of the dog].
2001 Nov 15
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
Antibiotic usage in Nordic countries.
2001 Sep
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
[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
Treatment of amatoxin poisoning: 20-year retrospective analysis.
2002
Antibiotics differ in their tendency to cause infusion phlebitis: a prospective observational study.
2002
Treatment of latent syphilis in HIV-infected patients with 10 d of benzylpenicillin G benethamine: a prospective study in Maputo, Mozambique.
2002
Gateways to Clinical Trials.
2002 Apr
[The Pneumococcal Observatory for the Central Region, 1 April 1999 to 31 March 2000].
2002 Apr
Immunoglobulin E binding determinants on beta-lactam drugs.
2002 Aug
Amoxicillin-induced exanthema in young adults with infectious mononucleosis: demonstration of drug-specific lymphocyte reactivity.
2002 Dec
Cysteine is exported from the Escherichia coli cytoplasm by CydDC, an ATP-binding cassette-type transporter required for cytochrome assembly.
2002 Dec 20
[Post-marketing surveillance of antibacterial activities of cefozopran against various clinical isolates--I. Gram-positive bacteria].
2002 Feb
Controlled administration of penicillin to patients with a positive history but negative skin and specific serum IgE tests.
2002 Feb
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
The 2.4-A crystal structure of the penicillin-resistant penicillin-binding protein PBP5fm from Enterococcus faecium in complex with benzylpenicillin.
2002 Jul
Liquid chromatographic determination of ampicillin residues in porcine muscle tissue by a multipenicillin analytical method: European Collaborative Study.
2002 Jul-Aug
Improved brain delivery of benzylpenicillin with a peptide-vector-mediated strategy.
2002 Jun
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
Expression and functional characterization of rat organic anion transporter 3 (rOat3) in the choroid plexus.
2002 May
[Use of antibiotics in general practice and at the Clinic for Infectious Diseases].
2002 May-Jun
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.
2002 Nov
Minimum inhibitory concentrations of 20 antimicrobial agents against Staphylococcus aureus isolated from bovine intramammary infections in Japan.
2002 Nov
Quality control of antibiotics before the implementation of an STD program in Northern Myanmar.
2002 Nov
Mechanism of the reduced elimination clearance of benzylpenicillin from cerebrospinal fluid in rats with intracisternal administration of lipopolysaccharide.
2002 Nov
Acyl-intermediate structures of the extended-spectrum class A beta-lactamase, Toho-1, in complex with cefotaxime, cephalothin, and benzylpenicillin.
2002 Nov 29
[Antimicrobial susceptibility of Streptococcus pneumoniae and Haemophilus influenzae isolated in major hospitals in Nagano Prefecture].
2002 Oct
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
Modulation of GABA(A) receptor-mediated currents by benzophenone derivatives in isolated rat Purkinje neurones.
2002 Sep
Benzylpenicillin differentially conjugates to IFN-gamma, TNF-alpha, IL-1beta, IL-4 and IL-13 but selectively reduces IFN-gamma activity.
2003 Feb
High-performance thin-layer chromatography-bioautography for multiple antibiotic residues in cow's milk.
2003 Feb 5
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

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
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 18:27:48 GMT 2023
Edited
by admin
on Fri Dec 15 18:27:48 GMT 2023
Record UNII
SSZ1S4I0US
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PENICILLIN G BENZATHINE ANHYDROUS
Common Name English
LENTOCILLIN
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 N,N'-BIS(PHENYLMETHYL)-1,2-ETHANEDIAMINE (2:1)
Common Name English
BENZILPENICILLINA BENZATINICA
Common Name English
VICIN
Common Name English
BENZATHINE BENZYLPENICILLIN [WHO-IP]
Common Name English
Benzathine benzylpenicillin [WHO-DD]
Common Name English
BENZATHINE BENZYLPENICILLIN ANHYDROUS
Common Name English
DEBECILLIN
Common Name English
PENDITAN
Common Name English
WYCILLINA
Common Name English
LEOMYPEN
Common Name English
BENZATHINI BENZYLPENICILLINUM [WHO-IP LATIN]
Common Name English
BENZATHINI BENZYLPENICILLINUM
WHO-IP LATIN  
Common Name English
PENADUR
Common Name English
PEN-DI-BEN
Common Name English
NEOLIN
Common Name English
BICA-PENICILLIN
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)
Common Name English
benzathine benzylpenicillin [INN]
Common Name English
PENDEPON
Common Name English
LONGACILINA
Common Name English
BENZETHACIL
Common Name English
LONGICIL
Common Name English
BENZATHIN PENICILLIN G
Common Name English
BENZAPEN
Common Name English
BENZATHINE BENZYLPENICILLINE
Common Name English
MOLDAMIN
Common Name English
PENICILLIN G BENZATHINE ANHYDROUS [MI]
Common Name English
DUROPENIN
Common Name English
PENIDURE
Common Name English
BENZATINA BENCILPENICILINA
Common Name English
BENZACILLIN
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3- DIMETHYL-7-OXO-6- (2-PHENYLACETAMIDO)-, COMPD. WITH N,N'- DIBENZYLETHYLENEDIAMINE (2:1)
Common Name English
4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 3,3- DIMETHYL-7-OXO-6-((2-PHENYLACETYL)AMINO)- (2S,5R,6R)-, COMPD. WITH N1,N2-BIS(PHENYLMETHYL)-1,2-ETHANEDIAMINE (2:1)
Common Name English
ETHYLENEDIAMINE, N,N'-DIBENZYL-, BIS(3,3-DIMETHYL-7-OXO-6- (2-PHENYLACETAMIDO)-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2- CARBOXYLATE)
Common Name English
CILLENTA
Common Name English
Classification Tree Code System Code
WHO-ATC J01CE08
Created by admin on Fri Dec 15 18:27:48 GMT 2023 , Edited by admin on Fri Dec 15 18:27:48 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID2047804
Created by admin on Fri Dec 15 18:27:48 GMT 2023 , Edited by admin on Fri Dec 15 18:27:48 GMT 2023
PRIMARY
ECHA (EC/EINECS)
216-260-5
Created by admin on Fri Dec 15 18:27:48 GMT 2023 , Edited by admin on Fri Dec 15 18:27:48 GMT 2023
PRIMARY
MERCK INDEX
m8475
Created by admin on Fri Dec 15 18:27:48 GMT 2023 , Edited by admin on Fri Dec 15 18:27:48 GMT 2023
PRIMARY
FDA UNII
SSZ1S4I0US
Created by admin on Fri Dec 15 18:27:48 GMT 2023 , Edited by admin on Fri Dec 15 18:27:48 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
PENICILLIN G BENZATHINE ANHYDROUS
Created by admin on Fri Dec 15 18:27:48 GMT 2023 , Edited by admin on Fri Dec 15 18:27:48 GMT 2023
PRIMARY Description: A white powder; odourless or almost odourless. Solubility: Very slightly soluble in water; sparingly soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Antibacterial drug. Storage: Benzathine benzylpenicillin should be kept in a tightly closed container, protected from light, and stored at a temperaturenot exceeding 30 ?C. Labelling: The designation sterile Benzathine benzylpenicillin indicates that the substance complies with the additionalrequirements for sterile Benzathine benzylpenicillin and may be used for parenteral administration or for other sterile applications. Additional information: Benzathine benzylpenicillin contains a variable amount of water of crystallization. Definition: Benzathine benzylpenicillin contains not less than 96.0% and not more than 100.5% of total penicillins calculated as (C16H18N2O4S)2,C16H20N2, and not less than 24.0% and not more than 27.0% of C16H20N2, both calculated with reference to the anhydrous substance.
NCI_THESAURUS
C169806
Created by admin on Fri Dec 15 18:27:48 GMT 2023 , Edited by admin on Fri Dec 15 18:27:48 GMT 2023
PRIMARY
CAS
1538-09-6
Created by admin on Fri Dec 15 18:27:48 GMT 2023 , Edited by admin on Fri Dec 15 18:27:48 GMT 2023
PRIMARY
INN
203
Created by admin on Fri Dec 15 18:27:48 GMT 2023 , Edited by admin on Fri Dec 15 18:27:48 GMT 2023
PRIMARY
PUBCHEM
15232
Created by admin on Fri Dec 15 18:27:48 GMT 2023 , Edited by admin on Fri Dec 15 18:27:48 GMT 2023
PRIMARY
CHEBI
51352
Created by admin on Fri Dec 15 18:27:48 GMT 2023 , Edited by admin on Fri Dec 15 18:27:48 GMT 2023
PRIMARY
DRUG BANK
DB09323
Created by admin on Fri Dec 15 18:27:48 GMT 2023 , Edited by admin on Fri Dec 15 18:27:48 GMT 2023
PRIMARY
EVMPD
SUB05741MIG
Created by admin on Fri Dec 15 18:27:48 GMT 2023 , Edited by admin on Fri Dec 15 18:27:48 GMT 2023
PRIMARY
SMS_ID
100000090509
Created by admin on Fri Dec 15 18:27:48 GMT 2023 , Edited by admin on Fri Dec 15 18:27:48 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS
SOLVATE->ANHYDROUS
Related Record Type Details
ACTIVE MOIETY
http://apps.who.int/phint/pdf/b/Jb.6.1.46.pdf