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
CC1(C)S[C@@H]2[C@H](NC(=O)CC3=CC=CC=C3)C(=O)N2[C@H]1C(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 Date2001 |
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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 Date2001 |
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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 Date2001 |
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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 Date2001 |
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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 Date2001 |
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 and cephalosporin biosynthesis: mechanism of carbon catabolite regulation of penicillin production. | 1999 Jan-Feb |
|
Successful shortening from seven to four days of parenteral beta-lactam treatment for common childhood infections: a prospective and randomized study. | 2001 |
|
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 |
|
[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 |
|
[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 |
|
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 |
|
[Allergic alteration of leukocytes in patients with drug intolerance]. | 2001 Sep-Oct |
|
Treatment of amatoxin poisoning: 20-year retrospective analysis. | 2002 |
|
Amoxicillin-induced exanthema in young adults with infectious mononucleosis: demonstration of drug-specific lymphocyte reactivity. | 2002 Dec |
|
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 |
|
Comparative in vitro activity of 16 antimicrobial agents against Actinobacillus pleuropneumoniae. | 2002 Jan |
|
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 |
|
Functional involvement of rat organic anion transporter 3 (rOat3; Slc22a8) in the renal uptake of organic anions. | 2002 Mar |
|
Quality control of antibiotics before the implementation of an STD program in Northern Myanmar. | 2002 Nov |
|
Fatal outcome from meningococcal disease--an association with meningococcal phenotype but not with reduced susceptibility to benzylpenicillin. | 2002 Oct |
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
Mon Mar 31 17:33:15 GMT 2025
by
admin
on
Mon Mar 31 17:33:15 GMT 2025
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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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Classification Tree | Code System | Code | ||
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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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Code System | Code | Type | Description | ||
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Q42T66VG0C
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PRIMARY | |||
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CHEMBL29
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PRIMARY | |||
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200-506-3
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PRIMARY | |||
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D010400
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PRIMARY | |||
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2082
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PRIMARY | |||
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61-33-6
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PRIMARY | |||
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Q42T66VG0C
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PRIMARY | |||
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193396
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PRIMARY | |||
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100000091070
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PRIMARY | |||
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BENZYLPENICILLIN
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PRIMARY | |||
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4796
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PRIMARY | |||
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C61883
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PRIMARY | |||
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SUB05772MIG
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PRIMARY | |||
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DB01053
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PRIMARY | |||
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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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PRIMARY | RxNorm |
Related Record | Type | Details | ||
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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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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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TRANSPORTER -> INHIBITOR | |||
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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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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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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PARENT -> IMPURITY |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Cmax | PHARMACOKINETIC |
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ROUTE OF ADMINSTRATION PHARMACOKINETIC PHARMACOKINETIC PHARMACOKINETIC |
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