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Benzylpenicillin

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
  • AU: A
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
Elimination half-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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E numberE705 (antibiotics) Edit this at Wikidata
CompTox Dashboard (EPA)
ECHA InfoCard100.000.461 Edit 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 as penicillin G (PenG[4]) or BENPEN,[5] is an antibiotic used to treat a number of bacterial infections.[6] This includes pneumonia, strep throat, syphilis, necrotizing enterocolitis, diphtheria, gas gangrene, leptospirosis, cellulitis, and tetanus.[6] It is not a first-line agent for pneumococcal meningitis.[6] Due to benzylpenicillin's limited bioavailability 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 by injection into a vein or muscle.[2] Two long-acting forms benzathine benzylpenicillin and procaine benzylpenicillin are available for use by injection into a muscle only.[6]

Side effects include diarrhea, seizures, and allergic reactions including anaphylaxis.[6] When used to treat syphilis or Lyme disease a reaction known as Jarisch–Herxheimer may occur.[6] It is not recommended in those with a history of penicillin allergy.[6] Use during pregnancy is generally safe in the penicillin and β-lactam class of medications.[6]

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

  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. ^ a b "Penicillin G Injection - FDA prescribing information, side effects and uses". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 10 December 2016.
  3. ^ Yip DW, Gerriets V (2023). "Penicillin". StatPearls. StatPearls Publishing. PMID 32119447. Retrieved 7 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. ^ a b c d e f g h Stuart MC, Kouimtzi M, Hill SR, eds. (2009). WHO Model Formulary 2008. World Health Organization. pp. 98, 105. hdl:10665/44053. ISBN 9789241547659.
  7. ^ Castle 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.

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