Benzylpenicillin, also known as penicillin G (PenG[3]) or BENPEN,[4] and in US military slang "Peanut Butter Shot"[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.[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]
Medical uses
Antimicrobial potency
As an antibiotic, benzylpenicillin is noted to possess effectiveness mainly against gram-positive organisms. Some gram-negative organisms such as Neisseria gonorrhoeae and Leptospira weilii are also reported to be susceptible to benzylpenicillin.[9]
Adverse effects
Adverse effects can include hypersensitivity reactions including urticaria, fever, joint pains, rashes, angioedema, anaphylaxis, serum sickness-like reaction. Rarely CNS 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.[10] In addition, Benzylpenicillin is an irritant, a health hazard, and an environmental hazard.[11]
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 with kidney failure, who may accumulate the drug due to reduced urinary excretion rates.[12][13]
Manufacture
Penicillin G is produced by fermentation of Penicillium chrysogenum.[14] The production of benzylpenicillin involves fermentation, recovery and purification of the penicillin.[15]
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.[16] 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.[17]
The recovery of the benzylpenicillin is the most important part of the production process because it affects the later purification steps if done incorrectly.[15] There are several types of techniques used to recover benzyl penicillin: aqueous two-phase extraction, liquid membrane extraction, microfiltration, and solvent extraction.[15] Extraction is more commonly used in the recovery process.[medical citation needed]
In the purification step, the benzylpencillin is separated from the extraction solution. This is normally done by using a separation column.[18]
Synonyms
Penicillin II (old UK nomenclature for naming penicillins)[19][20]
Wonder drug[21]
References
^David D. Dexter, James M. van der Veen (1978). "Conformations and a refinement of the structure of potassium penicillin G". J. Chem. Soc. Perkin Trans. 1. 3 (3): 185–190. doi:10.1039/p19780000185. PMID 565366.{{cite journal}}: CS1 maint: uses authors parameter (link)
^ ab"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.
^Dennis K. Flaherty (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.
^Kirkpatrick, Tim (11 February 2020). "Why the Most Dreaded Injection is Called the 'Peanut Butter' Shot". Military.com. Retrieved 21 December 2021.
^ abcdefghStuart MC, Kouimtzi M, Hill SR, eds. (2009). WHO Model Formulary 2008. World Health Organization. pp. 98, 105. hdl:10665/44053. ISBN 9789241547659.
^Castle, S. S. Penicillin G. In xPharm: The Comprehensive Pharmacology Reference; Enna, S. J., Bylund, D. B., Eds.; Elsevier: New York, 2007; 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.
^"Penicillin G" (PDF). Toku-E. 10 October 2010. Archived from the original (PDF) on 3 March 2016. Retrieved 11 June 2012.
^Castle, S. S. Penicillin G. In xPharm: The Comprehensive Pharmacology Reference; Enna, S. J., Bylund, D. B., Eds.; Elsevier: New York, 2007; pp 1-6.
^Anonymous Benzylpenicillin. https://www.acs.org/content/acs/en/molecule-of-the-week/archive/b/benzylpenicillin.html (accessed November 9, 2022).
^Fossieck B Jr, Parker RH. Neurotoxicity during intravenous infusion of penicillin. A review. J. Clin. Pharmacol. 14: 504–512, 1974.
^Baselt R (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 1195–1196.
^Anonymous Benzylpenicillin. https://www.acs.org/content/acs/en/molecule-of-the-week/archive/b/benzylpenicillin.html (accessed November 9, 2022).
^ 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.
^Barros J (4 January 2016). "Use Extraction to Improve Penicillin G Recovery". American Chemical Society. Archived from the original on 6 May 2019. Retrieved 6 May 2019.
^"Separation and Purification of Pharmaceuticals and Antibiotics" (PDF).
^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): 564–70. doi:10.1128/AAC.22.4.564. PMC 183794. PMID 6983856.
^Committee on Medical Research, O.S.R.D., Washington, and the Medical Research Council, London (1945). "Chemistry of Penicillin". Science. 102 (2660): 274–276. Bibcode:1947Ana....72..274R. doi:10.1039/an9477200274. PMID 20259048.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^"Penicillin G". PubChem. National Center for Biotechnology Information, National Library of Medicine. Retrieved 26 December 2020.
^Anonymous Benzylpenicillin. https://www.acs.org/content/acs/en/molecule-of-the-week/archive/b/benzylpenicillin.html (accessed November 9, 2022).
External links
"Benzylpenicillin". Drug Information Portal. U.S. National Library of Medicine.
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Antibacterials active on the cell wall and envelope (J01C-J01D)
Beta-lactams (inhibit synthesis of peptidoglycan layer of bacterial cell wall by binding to and inhibiting PBPs, a group of D-alanyl-D-alanine transpeptidases)
Availability of benzathine penicillin G for syphilis treatment in Shandong Province, Eastern China.
Chen X, Li G, Gan Y, Chu T, Liu D.
BMC health services research. 2019 Mar;19(1)188.
The shortage of benzathine penicillin G (BPG) worldwide presents a major challenge in the treatment of syphilis. Its availability for syphilis treatment has not been adequately evaluated in China. Two surveys were conducted among hospitals providing sexually transmitted infection clinical services i
Diagnosing acquired syphilis through oral lesions: the 12 year experience of an Oral Medicine Center.
Matias MDP, Jesus AO, Resende RG, Caldeira PC, Aguiar MCF.
Brazilian journal of otorhinolaryngology. 2019 Feb;().
A resurgence of syphilis in Brazil has been reported in recent years. With this in mind, the present study sought to investigate the frequency, demographics, and clinical characteristics of patients with acquired syphilis with oral involvement who received medical care at an Oral Medicine Reference
The Cochrane database of systematic reviews. 2019 02;2()CD012071.
Congenital syphilis continues to be a substantial public health problem in many parts of the world. Since the first use of penicillin for the treatment of syphilis in 1943, which was a notable early success, it has remained the preferred and standard treatment including for congenital syphilis. Howe
BICILLIN® L-A (penicillin G benzathine) This product information is intended only for residents of the United States. for Healthcare professionals: BICILLIN L-A U.S. Physician Prescribing Information This information—including product
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