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Benzathine benzylpenicillin

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Antibiotic

Pharmaceutical compound
Benzathine benzylpenicillin
Combination of
Benzylpenicillinantibiotic
Benzathinestabilizer
Clinical data
Trade namesBicillin L-A,[1] Permapen, others
Other namespenicillin benzathine benzyl, benzathine penicillin, penicillin G benzathine, benzylpenicillin benzathine[2]
AHFS/Drugs.comProfessional Drug Facts
License data
Pregnancy
category
Routes of
administration
Intramuscular injection[3]
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E numberE708(antibiotics)Edit this at Wikidata
CompTox Dashboard(EPA)
ECHA InfoCard100.014.782Edit this at Wikidata
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Benzathine benzylpenicillin, also known asbenzathine penicillin G (BPG), is anantibiotic medication useful for the treatment of a number ofbacterial infections.[3] Specifically it is used to treatstrep throat,diphtheria,syphilis, andyaws.[3][5] It is also used to preventrheumatic fever.[5] It is given byinjection into a muscle.[3][5] It is known as "Peanut Butter Shot" in USmilitary slang due to its viscosity.[6]

Side effects includeallergic reactions includinganaphylaxis, and the site of injection is notoriously painful.[5] When used to treat syphilis aJarisch–Herxheimer reaction may occur.[5] It is not recommended in those with a history ofpenicillin allergy or those with syphilis involving thenervous system.[5][3] Use duringpregnancy is generally safe.[3] It is in thepenicillin andbeta lactam class of medications and works viabenzylpenicillin.[3][5] Thebenzathine component slowly releases the penicillin making the combination long acting.[7]

Benzathine benzylpenicillin was patented in 1950.[2][8] It is on theWorld Health Organization's List of Essential Medicines.[9]

Medical uses

[edit]

It is used to treatstrep throat,diphtheria,syphilis, andyaws.[3][5]

Chemopreventive

[edit]

A single large 1.2-million-unit dose of intramuscular BPG is given to US military recruits. The Army in particular has a policy to inject all recruits if not allergic, though supply issues and individual base choices have reduced the coverage. A retrospective analysis shows that it reduces the rate of all-cause acute respiratory disease by 32% among Army recruits.[10]

Adverse effects

[edit]
2,400,000 units of Bicillin L-A brand of benzylpenicillin, for deep intramuscular injection
Further information:Penicillin drug reaction

The possible adverse effects are generally similar to other forms of penicillin. BPG is overall well-tolerated, but pain from the injection site is a common concern.[11]

Society and culture

[edit]

It is marketed by Pfizer (formerly by Wyeth) under the trade nameBicillin L-A.[12]

Compendial status

[edit]

References

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  1. ^Hamilton R (2015).Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 94.ISBN 9781284057560.
  2. ^abEngel J, Kleemann A, Kutscher B, Reichert D, eds. (2009).Pharmaceutical Substances: Syntheses, Patents and Applications of the most relevant APIs (5th ed.). Georg Thieme Verlag. p. 134.ISBN 9783131792754.Archived from the original on 20 December 2016.
  3. ^abcdefgh"Penicillin G Benzathine (Professional Patient Advice) - Drugs.com".www.drugs.com.Archived from the original on 20 December 2016. Retrieved10 December 2016.
  4. ^"Product monograph brand safety updates".Health Canada. 6 June 2024. Retrieved8 June 2024.
  5. ^abcdefghWorld Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.).WHO Model Formulary 2008. World Health Organization. pp. 98, 104.hdl:10665/44053.ISBN 9789241547659.
  6. ^Kirkpatrick T (11 February 2020)."Why the Most Dreaded Injection is Called the 'Peanut Butter' Shot".Military.com. Retrieved21 December 2021.
  7. ^Ebadi M (2007)."Penicillin G".Desk Reference of Clinical Pharmacology (2nd ed.). CRC Press. p. 555.ISBN 9781420047448.Archived from the original on 20 December 2016.
  8. ^US patent 2627491, Szabo JL, Bruce WF, "Penicillin salts of substituted alkylene diamines", published 3 February 1953, issued 3 February 1953, assigned to Wyeth LLC and Wyeth Inc 
  9. ^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.
  10. ^Ball JD, Prosperi MA, Brown A, Chen X, Kenah E, Yang Y, et al. (October 2018)."The role of benzathine penicillin G in predicting and preventing all-cause acute respiratory disease in military recruits: 1991-2017".Epidemiology and Infection.146 (14):1854–1860.doi:10.1017/S0950268818001838.PMC 9506690.PMID 29974837.
  11. ^Gartlan WA, Rahman S, Reti K (2023)."Benzathine Penicillin".StatPearls. StatPearls Publishing.PMID 29939545.
  12. ^"Bicillin® L-A"(PDF). US FDA. Archived fromthe original(PDF) on 30 March 2021. Retrieved31 July 2023.
  13. ^British Pharmacopoeia Commission Secretariat."Index (BP 2009)"(PDF). Archived fromthe original(PDF) on 11 April 2009. Retrieved26 March 2010.
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
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