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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H20N2.2C16H18N2O4S.H2O
Molecular Weight 927.139
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENICILLIN G BENZATHINE MONOHYDRATE

SMILES

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=OODAAHXHBAWPJQ-ZLOILWTKSA-N
InChI=1S/2C16H18N2O4S.C16H20N2.H2O/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;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 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 H2O
Molecular Weight 18.0153
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
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.
1999 May 7
Routine prophylactic antibiotic use in the management of snakebite.
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
Natural antibiotic susceptibility of strains of the Enterobacter cloacae complex.
2001 Dec
[CBO-guideline 'Bacterial meningitis'].
2001 Feb 3
Antimicrobial susceptibilities of Erysipelothrix rhusiopathiae isolated from pigs with swine erysipelas in Japan, 1988-1998.
2001 Mar
Contribution of alveolar phagocytes to antibiotic efficacy in an experimental lung infection with 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
Diagnostic evaluation of a large group of patients with immediate allergy to penicillins: the role of skin testing.
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
Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects.
2001 Sep-Oct
[Difficulties with using T lymphocyte culture as a method for diagnosing allergies to benzylpenicillin].
2002
Immunoglobulin E binding determinants on beta-lactam drugs.
2002 Aug
Controlled administration of penicillin to patients with a positive history but negative skin and specific serum IgE tests.
2002 Feb
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
Liquid chromatographic determination of ampicillin residues in porcine muscle tissue by a multipenicillin analytical method: European Collaborative Study.
2002 Jul-Aug
Evaluation of the new VITEK 2 system for determination of the susceptibility of clinical isolates of Streptococcus pneumoniae.
2002 Mar
[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
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
Benzylpenicillin differentially conjugates to IFN-gamma, TNF-alpha, IL-1beta, IL-4 and IL-13 but selectively reduces IFN-gamma activity.
2003 Feb
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 Sat Dec 16 09:26:55 GMT 2023
Edited
by admin
on Sat Dec 16 09:26:55 GMT 2023
Record UNII
C89ZJF1SVE
Record Status Validated (UNII)
Record Version
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Name Type Language
PENICILLIN G BENZATHINE MONOHYDRATE
Common Name English
1,2-ETHANEDIAMINE, N,N'-BIS(PHENYLMETHYL)-, BIS((2S-(2.ALPHA.,5.ALPHA.,6.BETA.))-3,3-DIMETHYL-7-OXO-6-((PHENYLACETYL)AMINO)-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLATE), MONOHYDRATE
Common Name English
BENZATHINE PENICILLIN G HYDRATE
Common Name English
ETHYLENEDIAMINE, N,N'-DIBENZYL-, COMPD. WITH PENICILLIN G (1:2), HYDRATE
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), HYDRATE
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 N,N'-BIS(PHENYLMETHYL)-1,2-ETHANEDIAMINE (2:1), MONOHYDRATE
Common Name English
1,2-ETHANEDIAMINE, N,N'-BIS(PHENYLMETHYL)-, BIS((2S,5R,6R)-3,3-DIMETHYL-7-OXO-6-((PHENYLACETYL)AMINO)-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLATE), MONOHYDRATE
Common Name English
BENZATHINE BENZYLPENICILLIN MONOHYDRATE
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), MONOHYDRATE
Systematic Name English
Code System Code Type Description
CAS
5928-83-6
Created by admin on Sat Dec 16 09:26:55 GMT 2023 , Edited by admin on Sat Dec 16 09:26:55 GMT 2023
PRIMARY
FDA UNII
C89ZJF1SVE
Created by admin on Sat Dec 16 09:26:55 GMT 2023 , Edited by admin on Sat Dec 16 09:26:55 GMT 2023
PRIMARY
PUBCHEM
22298952
Created by admin on Sat Dec 16 09:26:55 GMT 2023 , Edited by admin on Sat Dec 16 09:26:55 GMT 2023
PRIMARY
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ANHYDROUS->SOLVATE
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ACTIVE MOIETY