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
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
PubMed
Title | Date | PubMed |
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Penicillin-induced immune hemolytic anemia. Occurrence of massive intravascular hemolysis. | 1975 Aug 4 |
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Routine prophylactic antibiotic use in the management of snakebite. | 2001 |
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[Severe community-acquired pneumonia: etiology]. | 2001 |
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Optimisation of the prevention and treatment of bacterial endocarditis. | 2001 |
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Melatonin might be one possible medium of electroacupuncture anti-seizures. | 2001 |
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Encouraging good antimicrobial prescribing practice: a review of antibiotic prescribing policies used in the South East Region of England. | 2001 |
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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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[Epidemiological survey for hemolytic streptococci isolated from children in Tokyo]. | 2001 Apr |
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Short-term effects of four antibiotics on DNA synthesis in endothelial cells. | 2001 Apr |
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Selection of metalloenzymes by catalytic activity using phage display and catalytic elution. | 2001 Apr 2 |
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A theoretical study of the aminolysis reaction of lysine 199 of human serum albumin with benzylpenicillin: consequences for immunochemistry of penicillins. | 2001 Aug 8 |
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Gradient diffusion antibiotic susceptibility testing of potentially probiotic lactobacilli. | 2001 Dec |
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Natural antibiotic susceptibility of strains of the Enterobacter cloacae complex. | 2001 Dec |
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[Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine]. | 2001 Feb |
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Structures of the acyl-enzyme complexes of the Staphylococcus aureus beta-lactamase mutant Glu166Asp:Asn170Gln with benzylpenicillin and cephaloridine. | 2001 Feb 27 |
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[CBO-guideline 'Bacterial meningitis']. | 2001 Feb 3 |
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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 |
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[Cellulitis and necrotizing fasciitis: microbiology and pathogenesis]. | 2001 Mar |
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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 |
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Reaction of Lys-Tyr-Lys triad mimics with benzylpenicillin: insight into the role of Tyr150 in class C beta-lactamase. | 2001 May 7 |
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False penicillin resistance in Neisseria meningitidis following direct susceptibility tests from blood cultures. | 2001 Nov |
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[The use of veterinary drugs during pregnancy of the dog]. | 2001 Nov 15 |
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[Treatment of acute bacterial meningitis]. | 2001 Nov 20 |
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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 |
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Tetracycline-resistance genes of Clostridium perfringens, Clostridium septicum and Clostridium sordellii isolated from cattle affected with malignant edema. | 2001 Oct 22 |
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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 |
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Inhibition of translocation of beta -lactamase into the yeast endoplasmic reticulum by covalently bound benzylpenicillin. | 2001 Sep 14 |
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[Allergic alteration of leukocytes in patients with drug intolerance]. | 2001 Sep-Oct |
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Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects. | 2001 Sep-Oct |
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[Benzylpenicillin efficacy for neutropenic infection prophylaxis in patients with cancer and postcytostatic neutropenia]. | 2002 |
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[Difficulties with using T lymphocyte culture as a method for diagnosing allergies to benzylpenicillin]. | 2002 |
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Gateways to Clinical Trials. | 2002 Apr |
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3: Community-acquired pneumonia. | 2002 Apr 1 |
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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 |
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Chloramphenicol versus benzylpenicillin and gentamicin for the treatment of severe pneumonia in children in Papua New Guinea: a randomised trial. | 2002 Feb 9 |
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Comparative in vitro activity of 16 antimicrobial agents against Actinobacillus pleuropneumoniae. | 2002 Jan |
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Natural antibiotic susceptibility and biochemical profiles of Yersinia enterocolitica-like strains: Y. bercovieri, Y. mollaretii, Y. aldovae and 'Y. ruckeri'. | 2002 Jan |
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[Maximum residue levels (MRL's) of veterinary medicines in relation to food safety. MRL's really do matter--the Benzaprocpen case]. | 2002 Jan 1 |
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Primary (isolated) meningococcal pericarditis. | 2002 Jun |
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Fatality after an injection of Bicillin into the tonsillar fossa during an adenotonsillectomy. | 2002 Mar |
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Characterization of specific IgE response in vitro against protein and drug allergens using atopic and normal donors. | 2002 Mar |
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Evaluation of the new VITEK 2 system for determination of the susceptibility of clinical isolates of Streptococcus pneumoniae. | 2002 Mar |
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Functional involvement of rat organic anion transporter 3 (rOat3; Slc22a8) in the renal uptake of organic anions. | 2002 Mar |
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Major role of organic anion transporter 3 in the transport of indoxyl sulfate in the kidney. | 2002 May |
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[Use of antibiotics in general practice and at the Clinic for Infectious Diseases]. | 2002 May-Jun |
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Quality control of antibiotics before the implementation of an STD program in Northern Myanmar. | 2002 Nov |
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Fatal outcome from meningococcal disease--an association with meningococcal phenotype but not with reduced susceptibility to benzylpenicillin. | 2002 Oct |
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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 |
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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:
intravenously; intramuscularly
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.
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000011281
Created by
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NDF-RT |
N0000011281
Created by
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NCI_THESAURUS |
C1500
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NDF-RT |
N0000011281
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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LIVERTOX |
753
Created by
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FDA ORPHAN DRUG |
37689
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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WHO-ATC |
J01CE01
Created by
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WHO-VATC |
QS01AA14
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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WHO-ATC |
J01CE09
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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WHO-VATC |
QJ51CE01
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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CFR |
21 CFR 520.1696B
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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NDF-RT |
N0000011281
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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NDF-RT |
N0000175497
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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WHO-VATC |
QJ01CE01
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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FDA ORPHAN DRUG |
18787
Created by
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WHO-VATC |
QJ51RC22
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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NDF-RT |
N0000011281
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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NDF-RT |
N0000011281
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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NDF-RT |
N0000011281
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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WHO-ESSENTIAL MEDICINES LIST |
6.2.1
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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NDF-RT |
N0000011281
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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WHO-ATC |
S01AA14
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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NDF-RT |
N0000011281
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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WHO-VATC |
QG51AG02
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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Code System | Code | Type | Description | ||
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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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admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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PRIMARY | |||
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61-33-6
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admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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PRIMARY | |||
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BENZYLPENICILLIN
Created by
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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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DB01053
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PRIMARY | |||
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M8473
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PRIMARY | Merck Index | ||
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61-33-6
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PRIMARY | |||
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58
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PRIMARY | |||
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61-33-6
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PRIMARY | |||
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5904
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PRIMARY | |||
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61-33-6
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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PRIMARY | |||
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7980
Created by
admin on Mon Oct 21 19:47:38 UTC 2019 , Edited by admin on Mon Oct 21 19:47:38 UTC 2019
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PRIMARY | RxNorm |
ACTIVE MOIETY
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