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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-azabicycloheptane-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
3D model (JSmol)	Interactive image
SMILES CC1((N2(S1)(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) or BENPEN, is an antibiotic used to treat a number of bacterial infections. This includes pneumonia, strep throat, syphilis, necrotizing enterocolitis, diphtheria, gas gangrene, leptospirosis, cellulitis, and tetanus. It is not a first-line agent for pneumococcal meningitis. 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. Benzylpenicillin is given by injection into a vein or muscle. Two long-acting forms benzathine benzylpenicillin and procaine benzylpenicillin are available for use by injection into a muscle only.

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

Benzylpenicillin is on the World Health Organization's List of Essential Medicines.

Medical uses

Antimicrobial potency

As an antibiotic, benzylpenicillin is noted to possess effectiveness mainly against gram-positive organisms. Some gram-negative organisms such as Neisseria gonorrhoeae and Leptospira weilii are also reported to be susceptible to benzylpenicillin.

Adverse effects

Adverse effects can include hypersensitivity reactions including urticaria, fever, joint pains, rashes, angioedema, anaphylaxis, serum sickness-like reaction. Rarely central nervous system toxicity including convulsions (especially with high doses or in severe renal impairment), interstitial nephritis, haemolytic anaemia, leucopenia, thrombocytopenia, and coagulation disorders. Also reported diarrhoea (including antibiotic-associated colitis). Benzylpenicillin has relatively low toxicity, except for in the nervous system, in which it is one of the most active drugs among β-lactam agents. In addition, benzylpenicillin is a potential skin irritant and may cause breathing difficulties if inhaled.

Benzylpenicillin serum concentrations can be monitored either by traditional microbiological assay or by more modern chromatographic techniques. Such measurements can be useful to avoid central nervous system toxicity in any person receiving large doses of the drug on a chronic basis, but they are especially relevant to patients with kidney failure, who may accumulate the drug due to reduced urinary excretion rates.

Manufacture

Benzylpenicillin is produced by fermentation of Penicillium chrysogenum. The production of benzylpenicillin involves fermentation, recovery and purification of the penicillin.

The fermentation process of the production of benzylpenicillin creates the product. The presence of the product in solution inhibits the reaction and reduces the product rate and yield. Thus, in order to obtain the most product and increase the rate of reaction, it is continuously extracted. This is done by mixing the mold with either glucose, sucrose, lactose, starch, or dextrin, nitrate, ammonium salt, corn steep liquor, peptone, meat or yeast extract, and small amounts of inorganic salts.

The recovery of the benzylpenicillin is the most important part of the production process because it affects the later purification steps if done incorrectly. There are several techniques used to recover benzylpenicillin: aqueous two-phase extraction, liquid membrane extraction, microfiltration, and solvent extraction.

In the purification step, the benzylpenicillin is separated from the extraction solution. This is normally done by using a separation column.

Synonyms

• Penicillin II (old UK nomenclature for naming penicillins)
• Wonder drug

References

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.
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.
6. ^ Stuart MC, Kouimtzi M, Hill SR, eds. (2009). WHO Model Formulary 2008. World Health Organization. pp. 98, 105. hdl:10665/44053. ISBN 9789241547659.
7. ^ Castle SS (2007). "Penicillin G". In Enna SJ, Bylund DB (eds.). xPharm: The Comprehensive Pharmacology Reference. New York: Elsevier. pp. 1–6.
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.
9. "Penicillin G" (PDF). Toku-E. 10 October 2010. Archived from the original (PDF) on 3 March 2016. Retrieved 11 June 2012.
10. ^ "Benzylpenicillin". Molecule of the Week. American Chemical Society. Retrieved 9 November 2022.
11. Fossieck Jr B, Parker RH (October 1974). "Neurotoxicity during intravenous infusion of penicillin. A review". Journal of Clinical Pharmacology. 14 (10): 504–12. doi:10.1002/j.1552-4604.1974.tb01364.x. PMID 4610013. S2CID 40884225.
12. Baselt R (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 1195–1196.
13. ^ Liu Q, Li Y, Li W, Liang X, Zhang C, Liu H (February 2016). "Efficient Recovery of Penicillin G by a Hydrophobic Ionic Liquid". ACS Sustainable Chemistry & Engineering. 4 (2): 609–615. doi:10.1021/acssuschemeng.5b00975.
14. Barros J (4 January 2016). "Use Extraction to Improve Penicillin G Recovery". Discover Chemistry. American Chemical Society. Archived from the original on 6 May 2019. Retrieved 6 May 2019.
15. "Separation and Purification of Pharmaceuticals and Antibiotics" (PDF). Mitsubishi Chemical Corporation. pp. 312–324.
16. Saino Y, Kobayashi F, Inoue M, Mitsuhashi S (October 1982). "Purification and properties of inducible penicillin beta-lactamase isolated from Pseudomonas maltophilia". Antimicrobial Agents and Chemotherapy. 22 (4): 564–570. doi:10.1128/AAC.22.4.564. PMC 183794. PMID 6983856.
17. Robinson FA (July 1947). "Chemistry of penicillin". The Analyst. 72 (856): 274–276. Bibcode:1947Ana....72..274R. doi:10.1039/an9477200274. PMID 20259048.
18. "Penicillin G". PubChem. National Center for Biotechnology Information, National Library of Medicine. Retrieved 26 December 2020.

• Medicine

• Benzyl compounds
• Enantiopure drugs
• Glycine receptor agonists
• Penicillins
• World Health Organization essential medicines