Procaine benzylpenicillin

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Procaine benzylpenicillin
Combination of
Benzylpenicillinantibiotic
Procaineanaesthetic
Clinical data
Trade namesBicillin C-R,[1] other
Other namespenicillin G procaine, procaine penicillin G, procaine penicillin
AHFS/Drugs.comFDA Professional Drug Information
Routes of
administration		IM
ATC code
Legal status
Legal status
Identifiers
CAS Number
UNII
ChEMBL
E numberE707 (antibiotics) Edit this at Wikidata
CompTox Dashboard (EPA)
ECHA InfoCard100.000.187 Edit this at Wikidata
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Procaine benzylpenicillin also known as penicillin G procaine, is an antibiotic useful for the treatment of a number of bacterial infections.[2] Specifically it is used for syphilis, anthrax, mouth infections, pneumonia, diphtheria, cellulitis, and animal bites.[2] It is given by injection into a muscle.[2]

Side effects include pain at the site of injection, blood clotting problems, seizures, and allergic reactions including anaphylaxis.[2] When used to treat syphilis a reaction known as Jarisch-Herxheimer may occur.[2] It is not recommended in those with a history of penicillin allergy or procaine allergy.[1][2] Use during pregnancy and breastfeeding is relatively safe.[1][2] Procaine benzylpenicillin is in the penicillin and beta lactam family of medications.[2] It works via benzylpenicillin and results in bacterial death.[2][3] Procaine makes the combination long acting.[4]

Procaine benzylpenicillin was introduced for medical use in 1948.[3] It is on the World Health Organization's List of Essential Medicines.[5]

Medical uses

Specific indications for procaine penicillin include:[6]

  • Syphilis
    • In the United States, Bicillin C-R (an injectable suspension which 1.2 million units of benzathine penicillin and 1.2 million units of procaine penicillin per 4 ml) is not recommended for treating syphilis, since it contains only half the recommended dose of benzathine penicillin. Medication errors have been made due to the confusion between Bicillin L-A & Bicillin C-R.[7] As a result, changes in product packaging have been made; specifically, the statement "Not for the Treatment of Syphilis" has been added in red text to both the Bicillin CR and Billin CR 900/300 syringe labels.[8]
  • Respiratory tract infections where compliance with oral treatment is unlikely
  • Alongside Pen V and Erythromycin, Bicillin C-R is used to treat strep throat, given as one IM injection
  • Cellulitis, erysipelas
  • Procaine penicillin is also used as an adjunct in the treatment of anthrax.

Adverse effects

Further information: Penicillin drug reaction

At high doses procaine penicillin can cause seizures and CNS abnormalities due to procaine present in it.[citation needed]

Mechanism

It is a form of penicillin which is a salt of benzylpenicillin and the local anaesthetic agent procaine.[9] The salt has weak solubility, and is prepared as a suspension. Upon injection it forms a deposit within tissue (a "depot'), and the salt slowly dissolves into interstitial fluid - dissociating the two molecules into their bioactive forms over an extended period. Procaine acts as a local anaesthetic to reduce the discomfort of the depot, while benzylpenicillin enters into circulation and binds to bacterial cell walls, inhibiting their upkeep and production. This eventually leads to cell lysis (bursting). The term "hydrolyzed" is incorrectly used in some medical literature to describe the dissociation of the salt and resulting benzylpenicillin, but this is inaccurate - the molecules themselves are unchanged and no water is consumed in the reaction. The products are the two oppositely charged bioactive molecules.[10][11]

Compendial status

See also

References

  1. ^ a b c d Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 95. ISBN 9781284057560.
  2. ^ a b c d e f g h i World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 113, 607, 618. hdl:10665/44053. ISBN 9789241547659.
  3. ^ a b "Penicillin G Procaine - FDA prescribing information, side effects and uses". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 10 December 2016.
  4. ^ Ebadi M (2007). Desk Reference of Clinical Pharmacology, Second Edition. CRC Press. p. 555. ISBN 9781420047448. Archived from the original on 2016-12-20.
  5. ^ 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.
  6. ^ Rossi S, ed. (2006). Australian Medicines Handbook. Adelaide: Australian Medicines Handbook. ISBN 0-9757919-2-3.
  7. ^ Centers for Disease Control and Prevention (CDC) (2005). "Inadvertent use of Bicillin C-R to treat syphilis infection—Los Angeles, California, 1999–2004". MMWR Morb. Mortal. Wkly. Rep. 54 (9): 217–9. PMC 6820132. PMID 15758893.
  8. ^ United States Food & Drug Administration. "FDA Strengthens Labels of Two Specific Types of Antibiotics to Ensure Proper Use." Archived 2009-01-14 at the Wayback Machine Published December 1, 2004. Last accessed June 18, 2007.
  9. ^ Residues of Some Veterinary Drugs in Animals and Foods: Monographs Prepared by the Fiftieth Meeting of the Joint FAO/WHO Expert Committee on Food Additives : Rome, 17-26 February 1998. Food & Agriculture Org. 1999. p. 96. ISBN 9789251042809.
  10. ^ "Penicillin G Procaine". PubChem. U.S. National Library of Medicine. Retrieved 2025-01-13.
  11. ^ Tobin T, Tai CY, O'Leary J, Sturma L, Arnett S (April 1977). "Pharmacology of procaine in the horse: evidence against the existence of a 'procaine - penicillin' complex". American Journal of Veterinary Research. 38 (4): 437–442. PMID 851276.
  12. ^ 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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