Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H18N2O4S |
Molecular Weight | 334.39 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC3=CC=CC=C3)C(O)=O
InChI
InChIKey=JGSARLDLIJGVTE-MBNYWOFBSA-N
InChI=1S/C16H18N2O4S/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/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3245263 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | PENICILLIN G SODIUM Approved UsePenicillin 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 Date9.8314558E11 |
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Curative | PENICILLIN G SODIUM Approved UsePenicillin 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 Date9.8314558E11 |
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Curative | PENICILLIN G SODIUM Approved UsePenicillin 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 Date9.8314558E11 |
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Primary | PENICILLIN G SODIUM Approved UsePenicillin 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 Date9.8314558E11 |
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Primary | PENICILLIN G SODIUM Approved UsePenicillin 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 Date9.8314558E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.1 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21991307/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
65% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8218695/ |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/22273603/ Page: 6.0 |
yes [IC50 102 uM] | |||
yes [IC50 25 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/22273603/ Page: 4.0 |
yes | |||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
[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 |
|
Haemorrhagic cystitis and renal dysfunction associated with high dose benzylpenicillin. | 2000 Jan |
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Successful shortening from seven to four days of parenteral beta-lactam treatment for common childhood infections: a prospective and randomized study. | 2001 |
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Selection of metalloenzymes by catalytic activity using phage display and catalytic elution. | 2001 Apr 2 |
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Novel periodontal drug delivery system for treatment of periodontitis. | 2001 Apr 28 |
|
Gradient diffusion antibiotic susceptibility testing of potentially probiotic lactobacilli. | 2001 Dec |
|
Natural antibiotic susceptibility of strains of the Enterobacter cloacae complex. | 2001 Dec |
|
[Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine]. | 2001 Feb |
|
Molecular dynamics study of the IIA binding site in human serum albumin: influence of the protonation state of Lys195 and Lys199. | 2001 Jan 18 |
|
Degeneracy and additional alloreactivity of drug-specific human alpha beta(+) T cell clones. | 2001 Jul |
|
Epidemiology and diagnosis of meningitis: results of a five-year prospective, population-based study. | 2001 Jun |
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Benzylpenicillin-induced prolonged cholestasis. | 2001 Jun |
|
[Cellulitis and necrotizing fasciitis: microbiology and pathogenesis]. | 2001 Mar |
|
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 |
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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 |
|
Interaction of 2,3-dimercapto-1-propane sulfonate with the human organic anion transporter hOAT1. | 2001 Nov |
|
[Treatment of acute bacterial meningitis]. | 2001 Nov 20 |
|
Determination of benzylpenicillin, oxacillin, cloxacillin, and dicloxacillin in cows' milk by ion-pair high-performance liquid chromatography after precolumn derivatization. | 2001 Sep |
|
Diagnostic evaluation of a large group of patients with immediate allergy to penicillins: the role of skin testing. | 2001 Sep |
|
The VanY(D) DD-carboxypeptidase of Enterococcus faecium BM4339 is a penicillin-binding protein. | 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 |
|
Treatment of amatoxin poisoning: 20-year retrospective analysis. | 2002 |
|
Antibiotics differ in their tendency to cause infusion phlebitis: a prospective observational study. | 2002 |
|
Gateways to Clinical Trials. | 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 |
|
Comparative in vitro activity of 16 antimicrobial agents against Actinobacillus pleuropneumoniae. | 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 |
|
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 |
|
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 |
|
[Antimicrobial susceptibility of Streptococcus pneumoniae and Haemophilus influenzae isolated in major hospitals in Nagano Prefecture]. | 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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27511803
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
Edited
Fri Dec 16 15:46:59 UTC 2022
by
admin
on
Fri Dec 16 15:46:59 UTC 2022
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Record UNII |
Q42T66VG0C
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Record Status |
Validated (UNII)
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Record Version |
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-
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NDF-RT |
N0000011281
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NDF-RT |
N0000011281
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NCI_THESAURUS |
C1500
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NDF-RT |
N0000011281
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LIVERTOX |
NBK547993
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FDA ORPHAN DRUG |
37689
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WHO-ATC |
J01CE01
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WHO-VATC |
QS01AA14
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WHO-ATC |
J01CE09
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WHO-VATC |
QJ51CE01
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CFR |
21 CFR 520.1696B
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NDF-RT |
N0000011281
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NDF-RT |
N0000175497
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WHO-VATC |
QJ01CE01
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FDA ORPHAN DRUG |
18787
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WHO-VATC |
QJ51RC22
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NDF-RT |
N0000011281
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NDF-RT |
N0000011281
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NDF-RT |
N0000011281
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WHO-ESSENTIAL MEDICINES LIST |
6.2.1
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NDF-RT |
N0000011281
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WHO-ATC |
S01AA14
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NDF-RT |
N0000011281
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WHO-VATC |
QG51AG02
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Q42T66VG0C
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PRIMARY | |||
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CHEMBL29
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200-506-3
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D010400
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2082
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61-33-6
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Q42T66VG0C
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193396
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BENZYLPENICILLIN
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4796
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C61883
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SUB05772MIG
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DB01053
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M8473
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PRIMARY | Merck Index | ||
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58
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18208
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DTXSID5046934
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51354
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Penicillin G
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5904
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3166
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7980
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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EXCRETED UNCHANGED |
URINE
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Cmax | PHARMACOKINETIC |
|
ROUTE OF ADMINSTRATION PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC |
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