Benzathine benzylpenicillin

Benzathine benzylpenicillin, also known as benzathine penicillin G, is an antibiotic medication useful for the treatment of a number of bacterial infections.[3] Specifically it is used to treat strep throat, diphtheria, syphilis, and yaws.[3][4] It is also used to prevent rheumatic fever.[4] It is given by injection into a muscle.[3][4]

Benzathine benzylpenicillin
Combination of
Benzylpenicillinantibiotic
Benzathinestabilizer
Clinical data
Trade namesBicillin L-A,[1] Permapen, others
Other namespenicillin benzathine benzyl, benzathine penicillin, penicillin G benzathine, benethamine penicilline, benzylpenicillin benzathine[2]
AHFS/Drugs.comProfessional Drug Facts
License data
Pregnancy
category
  • AU: A
Routes of
administration		Intramuscular injection[3]
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E numberE708 (antibiotics)
CompTox Dashboard (EPA)
ECHA InfoCard100.014.782
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Side effects include allergic reactions including anaphylaxis, and pain at the site of injection.[4] When used to treat syphilis a reaction known as Jarisch-Herxheimer may occur.[4] It is not recommended in those with a history of penicillin allergy or those with syphilis involving the nervous system.[4][3] Use during pregnancy is generally safe.[3] It is in the penicillin and beta lactam class of medications and works via benzylpenicillin.[3][4] The benzathine component slowly releases the penicillin making the combination long acting.[5]

Benzathine benzylpenicillin was patented in 1950.[2][6] It is on the World Health Organization's List of Essential Medicines.[7]

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

Mechanism of action

It is in the penicillin class of medications. It is slowly absorbed into the circulation, after intramuscular injection, and hydrolysed to benzylpenicillin in vivo. It is the drug-of-choice when prolonged low concentrations of benzylpenicillin are required and appropriate, allowing prolonged antibiotic action over 2–4 weeks after a single IM dose.

Society and culture

It is marketed by Pfizer (formerly by Wyeth) under the trade name Bicillin L-A.[8]

Compendial status

References
  1. Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 94. ISBN 9781284057560.
  2. Engel 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. "Penicillin G Benzathine (Professional Patient Advice) - Drugs.com". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 10 December 2016.
  4. World 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.
  5. 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.
  6. US patent 2627491, Joseph Lester Szabo & William F Bruce, "Penicillin salts of substituted alkylene diamines", published 1953-02-03, issued 1953-02-03, assigned to Wyeth LLC and Wyeth Inc
  7. 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.
  8. "Bicillin® L-A" (PDF). US FDA. Retrieved 31 July 2023.
  9. British Pharmacopoeia Commission Secretariat. "Index (BP 2009)" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 26 March 2010.
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