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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H18N2O4S.C14H15N
Molecular Weight 531.666
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIBENZYLAMINE PENICILLIN G

SMILES

C(NCC1=CC=CC=C1)C2=CC=CC=C2.[H][C@]34SC(C)(C)[C@@H](N3C(=O)[C@H]4NC(=O)CC5=CC=CC=C5)C(O)=O

InChI

InChIKey=UPYLDHVPOPTZGP-LQDWTQKMSA-N
InChI=1S/C16H18N2O4S.C14H15N/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;1-3-7-13(8-4-1)11-15-12-14-9-5-2-6-10-14/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22);1-10,15H,11-12H2/t11-,12+,14-;/m1./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 C14H15N
Molecular Weight 197.2756
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 haemolytic anaemia. Communication of a case (author's transl)].
1975
Anaphylaxis manifested by hypotension alone.
1975 Jan
The optimization test in the guinea-pig. A method for the predictive evaluation of the contact allergenicity of chemicals.
1975 May
[Severe community-acquired pneumonia: etiology].
2001
Successful shortening from seven to four days of parenteral beta-lactam treatment for common childhood infections: a prospective and randomized study.
2001
[Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine].
2001 Feb
[CBO-guideline 'Bacterial meningitis'].
2001 Feb 3
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
Antimicrobial susceptibilities of Erysipelothrix rhusiopathiae isolated from pigs with swine erysipelas in Japan, 1988-1998.
2001 Mar
Application of ion-exchange cartridge clean-up in food analysis IV. Confirmatory assay of benzylpenicillin, phenoxymethylpenicillin, oxacillin, cloxacillin, nafcillin and dicloxacillin, in bovine tissues by liquid chromatography-electrospray ionization tandem mass spectrometry.
2001 Mar 16
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
Interaction of 2,3-dimercapto-1-propane sulfonate with the human organic anion transporter hOAT1.
2001 Nov
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
The VanY(D) DD-carboxypeptidase of Enterococcus faecium BM4339 is a penicillin-binding protein.
2001 Sep
Inhibition of translocation of beta -lactamase into the yeast endoplasmic reticulum by covalently bound benzylpenicillin.
2001 Sep 14
Antibiotics differ in their tendency to cause infusion phlebitis: a prospective observational study.
2002
Gateways to Clinical Trials.
2002 Apr
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
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
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
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 15:00:24 GMT 2023
Edited
by admin
on Fri Dec 15 15:00:24 GMT 2023
Record UNII
AF5F3C86Z1
Record Status Validated (UNII)
Record Version
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Name Type Language
DIBENZYLAMINE PENICILLIN G
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-(PHENYLMETHYL)BENZENEMETHANAMINE (1:1)
Systematic Name English
PENICILLIN G, COMPD. WITH DIBENZYLAMINE (1:1)
Common Name English
PENICILLIN, COMPD. WITH DIBENZYLAMINE
Common Name English
DIBENZYLAMINE PENICILLIN G DIBENZYLAMINE PENICILLIN G SALT
Common Name English
PENICILLIN G, DIBENZYLAMINE SALT
Common Name English
Code System Code Type Description
CAS
7173-27-5
Created by admin on Fri Dec 15 15:00:24 GMT 2023 , Edited by admin on Fri Dec 15 15:00:24 GMT 2023
PRIMARY
FDA UNII
AF5F3C86Z1
Created by admin on Fri Dec 15 15:00:24 GMT 2023 , Edited by admin on Fri Dec 15 15:00:24 GMT 2023
PRIMARY
PUBCHEM
197868
Created by admin on Fri Dec 15 15:00:24 GMT 2023 , Edited by admin on Fri Dec 15 15:00:24 GMT 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY