Benzathine benzylpenicillin

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Benzathine benzylpenicillin
Benzylpenicillin-Benzathin Structural Formula V.1.svg
Combination of
Clinical data
Trade namesBicillin L-A,[2] Permapen, others
Other namespenicillin benzathine benzyl, benzathine penicillin, penicillin G benzathine, benethamine penicilline, benzylpenicillin benzathine[3]
AHFS/Drugs.comProfessional Drug Facts
  • US: B (No risk in non-human studies) [1]
ATC code
CAS Number
PubChem CID
E numberE708 (antibiotics) Edit this at Wikidata
CompTox Dashboard (EPA)
ECHA InfoCard100.014.782 Edit this at Wikidata
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Benzathine benzylpenicillin, also known as benzathine penicillin G, is an antibiotic useful for the treatment of a number of bacterial infections.[1] Specifically it is to treat strep throat, diphtheria, syphilis, and yaws.[4][1] 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][1] Use during pregnancy is generally safe.[1] It is in the penicillin and beta lactam class of medications and works via benzylpenicillin.[1][4] The benzathine component slowly releases the penicillin making the combination long acting.[5]

Benzathine benzylpenicillin was patented in 1950.[3] It is on the World Health Organization's List of Essential Medicines, the safest and most effective medicines needed in a health system.[6] The wholesale cost in the developing world is about 0.27 to 1.71 USD for a course of treatment.[7] In the United States the medication costs 50 to 100 USD for a dose as of 2015.[2] In the United Kingdom it costs the NHS about 0.95 to 1.89 pounds a dose as of 2015.[8]

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. ^ a b c d e f "Penicillin G Benzathine (Professional Patient Advice) -". Archived from the original on 20 December 2016. Retrieved 10 December 2016.
  2. ^ a b Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 94. ISBN 9781284057560.
  3. ^ 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.
  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. ^ 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.
  7. ^ "Penicillin, Benzathine Benzyl". International Drug Price Indicator Guide. Retrieved 8 December 2016.
  8. ^ British national formulary : BNF 69 (69 ed.). British Medical Association. 2015. p. 367. ISBN 9780857111562.
  9. ^ British Pharmacopoeia Commission Secretariat. "Index (BP 2009)" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 26 March 2010.