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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
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
Penicillin-induced haemolytic anaemia associated with microangiopathy.
1976 Apr
Dual inhibitory activity of sitafloxacin (DU-6859a) against DNA gyrase and topoisomerase IV of Streptococcus pneumoniae.
1999 Oct
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
[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
A theoretical study of the aminolysis reaction of lysine 199 of human serum albumin with benzylpenicillin: consequences for immunochemistry of penicillins.
2001 Aug 8
Substrate binding and catalytic mechanism of class B beta-lactamases: a molecular modelling study.
2001 Dec
Gradient diffusion antibiotic susceptibility testing of potentially probiotic lactobacilli.
2001 Dec
[Allergy to penicillin: facts and controversies].
2001 Jun
Benzylpenicillin-induced prolonged cholestasis.
2001 Jun
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
False penicillin resistance in Neisseria meningitidis following direct susceptibility tests from blood cultures.
2001 Nov
Interaction of 2,3-dimercapto-1-propane sulfonate with the human organic anion transporter hOAT1.
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
Clinical evaluation of Pharmacia CAP System RAST FEIA amoxicilloyl and benzylpenicilloyl in patients with penicillin allergy.
2001 Sep
Inhibition of translocation of beta -lactamase into the yeast endoplasmic reticulum by covalently bound benzylpenicillin.
2001 Sep 14
Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects.
2001 Sep-Oct
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
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
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
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
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