Benzathine benzylpenicillin

Benzathine benzylpenicillin
Combination of
Benzylpenicillin antibiotic
Benzathine stabilizer
Clinical data
Trade names Bicillin L-A,[1] Permapen, others
Synonyms penicillin benzathine benzyl, benzathine penicillin, penicillin G benzathine, benethamine penicilline, benzylpenicillin benzathine[2]
AHFS/ Professional Drug Facts
  • US: B (No risk in non-human studies) [3]
    ATC code
    CAS Number
    PubChem CID
    E number E708 (antibiotics)
    ECHA InfoCard 100.014.782
     NY (what is this?)  (verify)

    Benzathine benzylpenicillin, also known as benzathine penicillin G, is an antibiotic useful for the treatment of a number of bacterial infections.[3] Specifically it is 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] It is on the World Health Organization's List of Essential Medicines, the most effective and safe 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.[1] In the United Kingdom it costs the NHS about 0.95 to 1.89 pounds a dose as of 2015.[8]

    Adverse effects

    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.

    Compendial status


    1. 1 2 Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 94. ISBN 9781284057560.
    2. 1 2 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. 1 2 3 4 5 6 "Penicillin G Benzathine (Professional Patient Advice) -". Archived from the original on 20 December 2016. Retrieved 10 December 2016.
    4. 1 2 3 4 5 6 7 WHO Model Formulary 2008 (PDF). World Health Organization. 2009. pp. 98, 104. ISBN 9789241547659. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016.
    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. "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived (PDF) from the original on 13 December 2016. Retrieved 8 December 2016.
    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.

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