Benzylpenicillin

Benzylpenicillin
	Ball and stick model. Legend:; Blue=nitrogen; red=oxygen; yellow=sulfur; grey=carbon and carbon bonds; white=hydrogen.
Clinical data
Trade names	Pfizerpen, other
Other names	Penicillin G potassium, penicillin G sodium
AHFS/Drugs.com	International Drug Names
MedlinePlus	a685013
Pregnancy; category	AU: A;
Routes of; administration	Intravenous therapy, intramuscular injection
ATC code	J01CE01 (WHO) S01AA14 (WHO) QJ51CE01 (WHO);
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	30% oral
Protein binding	60%
Metabolism	Liver
Elimination half-life	30 min
Excretion	Kidney
Identifiers
	IUPAC name (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;
CAS Number	61-33-6 (free acid); 69-57-8 (sodium salt);
PubChem CID	5904;
IUPHAR/BPS	4796;
DrugBank	DB01053 ;
ChemSpider	5693 ;
UNII	Q42T66VG0C;
KEGG	D02336 ;
ChEBI	CHEBI:18208 ;
ChEMBL	ChEMBL29 ;
E number	E705 (antibiotics)
CompTox Dashboard (EPA)	DTXSID5046934 ;
ECHA InfoCard	100.000.461
Chemical and physical data
Formula	C16H18N2O4S
Molar mass	334.39 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)Cc3ccccc3)C(=O)O)C;
	InChI InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1 ; Key:JGSARLDLIJGVTE-MBNYWOFBSA-N ;
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Benzylpenicillin, also known as penicillin G (PenG^[4]) or BENPEN,^[5] is an antibiotic used to treat a number of bacterial infections.^[6] This includes pneumonia, strep throat, syphilis, necrotizing enterocolitis, diphtheria, gas gangrene, leptospirosis, cellulitis, and tetanus.^[6] It is not a first-line agent for pneumococcal meningitis.^[6] Due to benzylpenicillin's limited bioavailability for oral medications, it is generally taken as an injection in the form of a sodium, potassium, benzathine, or procaine salt.^[7] Benzylpenicillin is given by injection into a vein or muscle.^[2] Two long-acting forms benzathine benzylpenicillin and procaine benzylpenicillin are available for use by injection into a muscle only.^[6]

Side effects include diarrhea, seizures, and allergic reactions including anaphylaxis.^[6] When used to treat syphilis or Lyme disease a reaction known as Jarisch–Herxheimer may occur.^[6] It is not recommended in those with a history of penicillin allergy.^[6] Use during pregnancy is generally safe in the penicillin and β-lactam class of medications.^[6]

Benzylpenicillin is on the World Health Organization's List of Essential Medicines.^[8]

^ Dexter DD, van der Veen JM (1978). "Conformations of penicillin G: crystal structure of procaine penicillin G monohydrate and a refinement of the structure of potassium penicillin G". Journal of the Chemical Society, Perkin Transactions 1. 3 (3): 185–190. doi:10.1039/p19780000185. PMID 565366.
^ ^a ^b "Penicillin G Injection - FDA prescribing information, side effects and uses". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 10 December 2016.
^ Yip DW, Gerriets V (2023). "Penicillin". StatPearls. StatPearls Publishing. PMID 32119447. Retrieved 7 December 2023.
^ Flaherty DK (2012). "Immunogenicity and Antigenicity". Immunology for Pharmacy. Mosby. ISBN 978-0-323-06947-2. Natural penicillin (PenG), penicillinase-resistant penicillin (methicillin), extended-spectrum penicillin (amoxicillin), and broad-spectrum penicillin (carbenicillin) all have the same core β-lactam ring, which is essential for antimicrobial activity.
^ "Australian Product Information – BENPEN" (PDF). Seqirus Pty Ltd.
^ ^a ^b ^c ^d ^e ^f ^g ^h Stuart MC, Kouimtzi M, Hill SR, eds. (2009). WHO Model Formulary 2008. World Health Organization. pp. 98, 105. hdl:10665/44053. ISBN 9789241547659.
^ Castle SS (2007). "Penicillin G". In Enna SJ, Bylund DB (eds.). xPharm: The Comprehensive Pharmacology Reference. New York: Elsevier. pp. 1–6.
^ 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.

[1] Dexter DD, van der Veen JM (1978). "Conformations of penicillin G: crystal structure of procaine penicillin G monohydrate and a refinement of the structure of potassium penicillin G". Journal of the Chemical Society, Perkin Transactions 1. 3 (3): 185–190. doi:10.1039/p19780000185. PMID 565366.

[Pro2016-2] "Penicillin G Injection - FDA prescribing information, side effects and uses". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 10 December 2016.

[3] Yip DW, Gerriets V (2023). "Penicillin". StatPearls. StatPearls Publishing. PMID 32119447. Retrieved 7 December 2023.

[4] Flaherty DK (2012). "Immunogenicity and Antigenicity". Immunology for Pharmacy. Mosby. ISBN 978-0-323-06947-2. Natural penicillin (PenG), penicillinase-resistant penicillin (methicillin), extended-spectrum penicillin (amoxicillin), and broad-spectrum penicillin (carbenicillin) all have the same core β-lactam ring, which is essential for antimicrobial activity.

[5] "Australian Product Information – BENPEN" (PDF). Seqirus Pty Ltd.

[WHO2008-6] ^ ^a ^b ^c ^d ^e ^f ^g ^h Stuart MC, Kouimtzi M, Hill SR, eds. (2009). WHO Model Formulary 2008. World Health Organization. pp. 98, 105. hdl:10665/44053. ISBN 9789241547659.

[Castle_2007-7] Castle SS (2007). "Penicillin G". In Enna SJ, Bylund DB (eds.). xPharm: The Comprehensive Pharmacology Reference. New York: Elsevier. pp. 1–6.

[WHO21st-8] 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.

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