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Benzylpenicillin

From Wikipedia, the free encyclopedia
(Redirected fromPenicillin G sodium)
Antibiotic medication

Pharmaceutical compound
Benzylpenicillin
Ball and stick model.[1] Legend:
Blue=nitrogen; red=oxygen; yellow=sulfur
grey=carbon and carbon bonds; white=hydrogen.
Clinical data
Trade namesPfizerpen, other
Other namesPenicillin G potassium,[2] penicillin G sodium
AHFS/Drugs.comInternational Drug Names
MedlinePlusa685013
Pregnancy
category
Routes of
administration
Intravenous therapy,intramuscular injection
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability30% oral[3]
Protein binding60%
MetabolismLiver
Eliminationhalf-life30 min
ExcretionKidney
Identifiers
  • (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E numberE705(antibiotics)Edit this at Wikidata
CompTox Dashboard(EPA)
ECHA InfoCard100.000.461Edit this at Wikidata
Chemical and physical data
FormulaC16H18N2O4S
Molar mass334.39 g·mol−1
3D model (JSmol)
  • CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)Cc3ccccc3)C(=O)O)C
  • 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 checkY
  • Key:JGSARLDLIJGVTE-MBNYWOFBSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Benzylpenicillin, also known aspenicillin G (PenG[4]) orBENPEN,[5] is anantibiotic used to treat a number ofbacterialinfections.[6] This includespneumonia,strep throat,syphilis,necrotizing enterocolitis,diphtheria,gas gangrene,leptospirosis,cellulitis, andtetanus.[6] It is not a first-line agent forpneumococcalmeningitis.[6] Due to benzylpenicillin's limitedbioavailability for oral medications, it is generally taken as an injection in the form of a sodium, potassium, benzathine, or procaine salt.[7] Benzylpenicillin is given byinjection into a vein ormuscle.[2] Two long-acting formsbenzathine benzylpenicillin andprocaine benzylpenicillin are available for use byinjection into a muscle only.[6]

Side effects includediarrhea,seizures, andallergic reactions includinganaphylaxis.[6] When used to treat syphilis or Lyme disease a reaction known asJarisch–Herxheimer may occur.[6] It is not recommended in those with a history ofpenicillin allergy.[6] Use during pregnancy is generally safe in thepenicillin andβ-lactam class of medications.[6]

Benzylpenicillin is on theWorld Health Organization's List of Essential Medicines.[8]

Medical uses

[edit]

Antimicrobial potency

[edit]

As an antibiotic, benzylpenicillin is noted to possess effectiveness mainly againstgram-positive organisms. Somegram-negative organisms such asNeisseria gonorrhoeae andLeptospira weilii are also reported to be susceptible to benzylpenicillin.[9]

Adverse effects

[edit]

Adverse effects can include hypersensitivity reactions including urticaria, fever, joint pains, rashes, angioedema, anaphylaxis, serum sickness-like reaction. Rarely central nervous system toxicity including convulsions (especially with high doses or in severe renal impairment), interstitial nephritis, haemolytic anaemia, leucopenia, thrombocytopenia, and coagulation disorders. Also reported diarrhoea (including antibiotic-associated colitis). Benzylpenicillin has relatively low toxicity, except for in the nervous system, in which it is one of the most active drugs among β-lactam agents.[7] In addition, benzylpenicillin is a potential skin irritant and may cause breathing difficulties if inhaled.[10]

Benzylpenicillin serum concentrations can be monitored either by traditional microbiological assay or by more modern chromatographic techniques. Such measurements can be useful to avoid central nervous system toxicity in any person receiving large doses of the drug on a chronic basis, but they are especially relevant to patients withkidney failure, who may accumulate the drug due to reduced urinary excretion rates.[11][12]

Manufacture

[edit]

Benzylpenicillin is produced by fermentation ofPenicillium chrysogenum.[10] The production of benzylpenicillin involves fermentation, recovery and purification of the penicillin.[13]

The fermentation process of the production of benzylpenicillin creates the product. The presence of the product in solution inhibits the reaction and reduces the product rate and yield. Thus, in order to obtain the most product and increase the rate of reaction, it is continuously extracted.[14] This is done by mixing the mold with either glucose, sucrose, lactose, starch, or dextrin, nitrate, ammonium salt, corn steep liquor, peptone, meat or yeast extract, and small amounts of inorganic salts.[15]

The recovery of the benzylpenicillin is the most important part of the production process because it affects the later purification steps if done incorrectly.[13] There are several techniques used to recover benzylpenicillin: aqueous two-phase extraction, liquid membrane extraction, microfiltration, and solvent extraction.[13]

In the purification step, the benzylpenicillin is separated from the extraction solution. This is normally done by using a separation column.[16]

Synonyms

[edit]
  • Penicillin II (old UK nomenclature for naming penicillins)[17][18]
  • Wonder drug[10]

References

[edit]
  1. ^Dexter DD, van der Veen JM (1978). "Conformations of penicillin G: crystal structure of procaine penicillin G monohydrate and a refinement of the structure of potassium penicillin G".Journal of the Chemical Society, Perkin Transactions 1.3 (3):185–190.doi:10.1039/p19780000185.PMID 565366.
  2. ^ab"Penicillin G Injection - FDA prescribing information, side effects and uses".www.drugs.com.Archived from the original on 20 December 2016. Retrieved10 December 2016.
  3. ^Yip DW, Gerriets V (2023)."Penicillin".StatPearls. StatPearls Publishing.PMID 32119447. Retrieved7 December 2023.
  4. ^Flaherty DK (2012). "Immunogenicity and Antigenicity".Immunology for Pharmacy. Mosby.ISBN 978-0-323-06947-2.Natural penicillin (PenG), penicillinase-resistant penicillin (methicillin), extended-spectrum penicillin (amoxicillin), and broad-spectrum penicillin (carbenicillin) all have the same core β-lactam ring, which is essential for antimicrobial activity.
  5. ^"Australian Product Information – BENPEN"(PDF).Seqirus Pty Ltd.
  6. ^abcdefghStuart MC, Kouimtzi M, Hill SR, eds. (2009).WHO Model Formulary 2008. World Health Organization. pp. 98, 105.hdl:10665/44053.ISBN 9789241547659.
  7. ^abCastle SS (2007). "Penicillin G". In Enna SJ, Bylund DB (eds.).xPharm: The Comprehensive Pharmacology Reference. New York: Elsevier. pp. 1–6.
  8. ^World Health Organization (2019).World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization.hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  9. ^"Penicillin G"(PDF). Toku-E. 10 October 2010. Archived fromthe original(PDF) on 3 March 2016. Retrieved11 June 2012.
  10. ^abc"Benzylpenicillin".Molecule of the Week. American Chemical Society. Retrieved9 November 2022.
  11. ^Fossieck Jr B, Parker RH (October 1974). "Neurotoxicity during intravenous infusion of penicillin. A review".Journal of Clinical Pharmacology.14 (10):504–12.doi:10.1002/j.1552-4604.1974.tb01364.x.PMID 4610013.S2CID 40884225.
  12. ^Baselt R (2008).Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 1195–1196.
  13. ^abcLiu Q, Li Y, Li W, Liang X, Zhang C, Liu H (February 2016). "Efficient Recovery of Penicillin G by a Hydrophobic Ionic Liquid".ACS Sustainable Chemistry & Engineering.4 (2):609–615.doi:10.1021/acssuschemeng.5b00975.
  14. ^Barros J (4 January 2016)."Use Extraction to Improve Penicillin G Recovery".Discover Chemistry. American Chemical Society. Archived fromthe original on 6 May 2019. Retrieved6 May 2019.
  15. ^"Separation and Purification of Pharmaceuticals and Antibiotics"(PDF). Mitsubishi Chemical Corporation. pp. 312–324.
  16. ^Saino Y, Kobayashi F, Inoue M, Mitsuhashi S (October 1982)."Purification and properties of inducible penicillin beta-lactamase isolated from Pseudomonas maltophilia".Antimicrobial Agents and Chemotherapy.22 (4):564–570.doi:10.1128/AAC.22.4.564.PMC 183794.PMID 6983856.
  17. ^Robinson FA (July 1947). "Chemistry of penicillin".The Analyst.72 (856):274–276.Bibcode:1947Ana....72..274R.doi:10.1039/an9477200274.PMID 20259048.
  18. ^"Penicillin G".PubChem. National Center for Biotechnology Information, National Library of Medicine. Retrieved26 December 2020.
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases
)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems /Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Siderophore
Veterinary
Monobactams
β-lactamase inhibitors
Combinations
Polypeptides
Lipopeptides
Other
  • Inhibits PG elongation and crosslinking:Ramoplanin§
Intracellular
Other
Receptor
(ligands)
GlyRTooltip Glycine receptor
NMDARTooltip N-Methyl-D-aspartate receptor
Transporter
(blockers)
GlyT1Tooltip Glycine transporter 1
GlyT2Tooltip Glycine transporter 2
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