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

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 of PENICILLIN G BENZATHINE

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 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 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 C16H18N2O4S
Molecular Weight 334.39
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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 haemolytic anaemia. Communication of a case (author's transl)].
1975
Anaphylaxis manifested by hypotension alone.
1975 Jan
Fresh vs aged benzylpenicillin on non-IgE responses in mice.
1998 Jan
Dual inhibitory activity of sitafloxacin (DU-6859a) against DNA gyrase and topoisomerase IV of Streptococcus pneumoniae.
1999 Oct
Haemorrhagic cystitis and renal dysfunction associated with high dose benzylpenicillin.
2000 Jan
Drug-induced hemolysis: cefotetan-dependent hemolytic anemia mimicking an acute intravascular immune transfusion reaction.
2000 May
Encouraging good antimicrobial prescribing practice: a review of antibiotic prescribing policies used in the South East Region of England.
2001
Gradient diffusion antibiotic susceptibility testing of potentially probiotic lactobacilli.
2001 Dec
Insights into the molecular basis for the carbenicillinase activity of PSE-4 beta-lactamase from crystallographic and kinetic studies.
2001 Jan 16
Molecular dynamics study of the IIA binding site in human serum albumin: influence of the protonation state of Lys195 and Lys199.
2001 Jan 18
[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
[Allergy to penicillin: facts and controversies].
2001 Jun
[Hoigne syndrome as an acute non-allergic reaction to different drugs: case reports].
2001 Jun
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
Purification and characterization of a beta-lactamase from Haemophilus ducreyi in Escherichia coli.
2001 Oct
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
Marked differences in antibiotic use and resistance between university hospitals in Vilnius, Lithuania, and Huddinge, Sweden.
2001 Winter
[The Pneumococcal Observatory for the Central Region, 1 April 1999 to 31 March 2000].
2002 Apr
Amoxicillin-induced exanthema in young adults with infectious mononucleosis: demonstration of drug-specific lymphocyte reactivity.
2002 Dec
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
Evaluation of the new VITEK 2 system for determination of the susceptibility of clinical isolates of Streptococcus pneumoniae.
2002 Mar
Expression and functional characterization of rat organic anion transporter 3 (rOat3) in the choroid plexus.
2002 May
[Antimicrobial susceptibility of Streptococcus pneumoniae and Haemophilus influenzae isolated in major hospitals in Nagano Prefecture].
2002 Oct
Biochemical characterization of a novel extended-spectrum beta-lactamase from Pseudomonas aeruginosa 802.
2002 Spring
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 14:59:10 GMT 2023
Edited
by admin
on Fri Dec 15 14:59:10 GMT 2023
Record UNII
RIT82F58GK
Record Status Validated (UNII)
Record Version
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Name Type Language
PENICILLIN G BENZATHINE
GREEN BOOK   MI   ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
PENICILLIN G BENZATHINE [GREEN BOOK]
Common Name English
BENZATHINE BENZYLPENICILLIN [MART.]
Common Name English
BENZATHINE BENZYLPENICILLIN
MART.  
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
JAN  
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
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
WHO-ATC J01CE08
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
CFR 21 CFR 522.1696A
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
WHO-VATC QJ51RC24
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
NCI_THESAURUS C1500
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
WHO-VATC QJ01CE08
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
Code System Code Type Description
DAILYMED
RIT82F58GK
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY
DRUG CENTRAL
4347
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY
LACTMED
Benzathine Penicillin G
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY
ChEMBL
CHEMBL29
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY
MESH
D010401
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY
RS_ITEM_NUM
1502009
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY
EVMPD
SUB37626
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY
EPA CompTox
DTXSID00194317
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY
FDA UNII
RIT82F58GK
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY
RXCUI
7982
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY RxNorm
SMS_ID
100000129194
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY
PUBCHEM
656811
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY
MERCK INDEX
m8475
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY Merck Index
CAS
41372-02-5
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY
WIKIPEDIA
BENZATHINE BENZYLPENICILLIN
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY
NCI_THESAURUS
C47657
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY
DRUG BANK
DBSALT002769
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY
CHEBI
51352
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY
EVMPD
SUB05741MIG
Created by admin on Fri Dec 15 14:59:10 GMT 2023 , Edited by admin on Fri Dec 15 14:59:10 GMT 2023
PRIMARY
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