Back Bensielpenisillien AF بنزيل بنسيلين Arabic بنزیل پنیسیلین AZB Бензилпенициллин BA Benzilpenicilin BS Benzilpenicil·lina Catalan Бензилпенициллин CV Bensylpenisilin CY Benzylpenicillin Danish Benzylpenicillin German
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| Clinical data | |
|---|---|
| Trade names | Pfizerpen, other |
| Other names | Penicillin G potassium,[2] penicillin G sodium |
| AHFS/Drugs.com | International Drug Names |
| MedlinePlus | a685013 |
| Pregnancy category |
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| Routes of administration | Intravenous therapy, intramuscular injection |
| ATC code | |
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| Legal status |
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| Pharmacokinetic data | |
| Bioavailability | 30% oral [3] |
| Protein binding | 60% |
| Metabolism | Liver |
| Elimination half-life | 30 min |
| Excretion | Kidney |
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| IUPHAR/BPS | |
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| ChEBI | |
| ChEMBL | |
| E number | E705 (antibiotics) |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.000.461 |
| Chemical and physical data | |
| Formula | C16H18N2O4S |
| Molar mass | 334.39 g·mol−1 |
| 3D model (JSmol) | |
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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]
- ^ 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.
- ^ 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.
- ^ Yip DW, Gerriets V (2023). "Penicillin". StatPearls. StatPearls Publishing. PMID 32119447. Retrieved 7 December 2023.
- ^ 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.
- ^ "Australian Product Information – BENPEN" (PDF). Seqirus Pty Ltd.
- ^ 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.
- ^ Castle SS (2007). "Penicillin G". In Enna SJ, Bylund DB (eds.). xPharm: The Comprehensive Pharmacology Reference. New York: Elsevier. pp. 1–6.
- ^ 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.