Benzathine benzylpenicillin

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search

Benzathine benzylpenicillin
Benzylpenicillin-Benzathin Structural Formula V.1.svg
Combination of
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
  • AU: A
Routes of
ATC code
Legal status
Legal status
CAS Number
PubChem CID
E numberE708 (antibiotics) Edit this at Wikidata
CompTox Dashboard (EPA)
ECHA InfoCard100.014.782 Edit this at Wikidata
 ☒NcheckY (what is this?)  (verify)

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.[4][3] It is also used to prevent rheumatic fever.[4] It is given by injection into a muscle.[4]

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[edit]

2,400,000 units of Bicillin L-A brand of benzylpenicillin, for deep intramuscular injection

Mechanism of action[edit]

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[edit]

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

Compendial status[edit]


  1. ^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 94. ISBN 9781284057560.
  2. ^ a b Engel, Jürgen; Kleemann, Axel; Kutscher, Bernhard; Reichert, Dietmar (2014). Pharmaceutical Substances, 5th Edition, 2009: Syntheses, Patents and Applications of the most relevant APIs (5 ed.). Georg Thieme Verlag. p. 134. ISBN 9783131792754. Archived from the original on 20 December 2016.
  3. ^ a b c d e "Penicillin G Benzathine (Professional Patient Advice) -". Archived from the original on 20 December 2016. Retrieved 10 December 2016.
  4. ^ a b c d e f g 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, Manuchair (2007). Desk Reference of Clinical Pharmacology, Second Edition (2 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. ^ British Pharmacopoeia Commission Secretariat. "Index (BP 2009)" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 26 March 2010.

External links[edit]