Benzylpenicillin

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Benzylpenicillin
Benzylpenicillin.svg
Benzylpenicillin-anion-from-xtal-3D-bs-17.png
Ball and stick model. [1] Legend:
Blue=nitrogen; red=oxygen; yellow=sulfur
grey=carbon and carbon bonds; white=hydrogen.
Clinical data
Trade names Pfizerpen, other
Other namesPenicillin G potassium, [2] penicillin G sodium
AHFS/Drugs.com International Drug Names
MedlinePlus a685013
Pregnancy
category
  • AU:A
Routes of
administration 		Intravenous therapy, intramuscular injection
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 30% oral [3]
Protein binding 60%
Metabolism Liver
Elimination half-life 30 min
Excretion Kidney
Identifiers
  • (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number E705 (antibiotics) OOjs UI icon edit-ltr-progressive.svg
CompTox Dashboard (EPA)
ECHA InfoCard 100.000.461 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C16H18N2O4S
Molar mass 334.39 g·mol−1
3D model (JSmol)
  • CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)Cc3ccccc3)C(=O)O)C
  • 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 Yes check.svgY
  • Key:JGSARLDLIJGVTE-MBNYWOFBSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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]

Contents

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]

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. [9]

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. [7] In addition, benzylpenicillin is an irritant, a health hazard, and an environmental hazard. [10]

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. [11] [12]

Manufacture

Benzylpenicillin is produced by fermentation of Penicillium chrysogenum . [10] The production of benzylpenicillin involves fermentation, recovery and purification of the penicillin. [13]

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. [14] 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. [15]

The recovery of the benzylpenicillin is the most important part of the production process because it affects the later purification steps if done incorrectly. [13] There are several techniques used to recover benzylpenicillin: aqueous two-phase extraction, liquid membrane extraction, microfiltration, and solvent extraction. [13] Extraction is more commonly used in the recovery process.[ medical citation needed ]

In the purification step, the benzylpenicillin is separated from the extraction solution. This is normally done by using a separation column. [16]

Synonyms

Related Research Articles

<span class="mw-page-title-main">Penicillin</span> Group of antibiotics derived from Penicillium fungi

Penicillins are a group of β-lactam antibiotics originally obtained from Penicillium moulds, principally P. chrysogenum and P. rubens. Most penicillins in clinical use are synthesised by P. chrysogenum using deep tank fermentation and then purified. A number of natural penicillins have been discovered, but only two purified compounds are in clinical use: penicillin G and penicillin V. Penicillins were among the first medications to be effective against many bacterial infections caused by staphylococci and streptococci. They are still widely used today for different bacterial infections, though many types of bacteria have developed resistance following extensive use.

<span class="mw-page-title-main">Beta-lactam antibiotics</span> Class of broad-spectrum antibiotics

β-lactam antibiotics are antibiotics that contain a beta-lactam ring in their chemical structure. This includes penicillin derivatives (penams), cephalosporins and cephamycins (cephems), monobactams, carbapenems and carbacephems. Most β-lactam antibiotics work by inhibiting cell wall biosynthesis in the bacterial organism and are the most widely used group of antibiotics. Until 2003, when measured by sales, more than half of all commercially available antibiotics in use were β-lactam compounds. The first β-lactam antibiotic discovered, penicillin, was isolated from a strain of Penicillium rubens.

<span class="mw-page-title-main">Ertapenem</span> Antibiotic medication

Ertapenem, sold under the brand name Invanz, is a carbapenem antibiotic medication used for the treatment of infections of the abdomen, the lungs, the upper part of the female reproductive system, and the diabetic foot.

<span class="mw-page-title-main">Aztreonam</span> Chemical compound

Aztreonam, sold under the brand name Azactam among others, is an antibiotic used primarily to treat infections caused by gram-negative bacteria such as Pseudomonas aeruginosa. This may include bone infections, endometritis, intra abdominal infections, pneumonia, urinary tract infections, and sepsis. It is given by intravenous or intramuscular injection or by inhalation.

<span class="mw-page-title-main">Cloxacillin</span> Beta-lactam antibiotic

Cloxacillin is an antibiotic useful for the treatment of a number of bacterial infections. This includes impetigo, cellulitis, pneumonia, septic arthritis, and otitis externa. It is not effective for methicillin-resistant Staphylococcus aureus (MRSA). It can be used by mouth and by injection.

<span class="mw-page-title-main">Ceftriaxone</span> Antibiotic medication

Ceftriaxone, sold under the brand name Rocephin, is a third-generation cephalosporin antibiotic used for the treatment of a number of bacterial infections. These include middle ear infections, endocarditis, meningitis, pneumonia, bone and joint infections, intra-abdominal infections, skin infections, urinary tract infections, gonorrhea, and pelvic inflammatory disease. It is also sometimes used before surgery and following a bite wound to try to prevent infection. Ceftriaxone can be given by injection into a vein or into a muscle.

<span class="mw-page-title-main">Amoxicillin/clavulanic acid</span> Combination antibiotic drug

Amoxicillin/clavulanic acid, also known as co-amoxiclav or amox-clav, sold under the brand name Augmentin, among others, is an antibiotic medication used for the treatment of a number of bacterial infections. It is a combination consisting of amoxicillin, a β-lactam antibiotic, and potassium clavulanate, a β-lactamase inhibitor. It is specifically used for otitis media, streptococcal pharyngitis, pneumonia, cellulitis, urinary tract infections, and animal bites. It is taken by mouth or by injection into a vein.

<span class="mw-page-title-main">Cefalexin</span> Beta-lactam antibiotic

Cefalexin, also spelled cephalexin, is an antibiotic that can treat a number of bacterial infections. It kills gram-positive and some gram-negative bacteria by disrupting the growth of the bacterial cell wall. Cefalexin is a β-lactam antibiotic within the class of first-generation cephalosporins. It works similarly to other agents within this class, including intravenous cefazolin, but can be taken by mouth.

<span class="mw-page-title-main">Meropenem</span> Broad-spectrum antibiotic

Meropenem, sold under the brand name Merrem among others, is an intravenous β-lactam antibiotic used to treat a variety of bacterial infections. Some of these include meningitis, intra-abdominal infection, pneumonia, sepsis, and anthrax.

<span class="mw-page-title-main">Cefotaxime</span> Chemical compound

Cefotaxime is an antibiotic used to treat a number of bacterial infections in human, other animals and plant tissue culture. Specifically in humans it is used to treat joint infections, pelvic inflammatory disease, meningitis, pneumonia, urinary tract infections, sepsis, gonorrhea, and cellulitis. It is given either by injection into a vein or muscle.

<span class="mw-page-title-main">Flucloxacillin</span> Penicillin

Flucloxacillin, also known as floxacillin, is an antibiotic used to treat skin infections, external ear infections, infections of leg ulcers, diabetic foot infections, and infection of bone. It may be used together with other medications to treat pneumonia, and endocarditis. It may also be used prior to surgery to prevent Staphylococcus infections. It is not effective against methicillin-resistant Staphylococcus aureus (MRSA). It is taken by mouth or given by injection into a vein or muscle.

<span class="mw-page-title-main">Oxacillin</span> Chemical compound

Oxacillin is a narrow-spectrum beta-lactam antibiotic of the penicillin class developed by Beecham.

<span class="mw-page-title-main">Phenoxymethylpenicillin</span> Antibiotic medication

Phenoxymethylpenicillin, also known as penicillin V (PcV) and penicillin VK, is an antibiotic useful for the treatment of a number of bacterial infections. Specifically it is used for the treatment of strep throat, otitis media, and cellulitis. It is also used to prevent rheumatic fever and to prevent infections following removal of the spleen. It is given by mouth.

<span class="mw-page-title-main">Benzathine benzylpenicillin</span> Antibiotic

Benzathine benzylpenicillin, also known as benzathine penicillin G (BPG), is an antibiotic medication useful for the treatment of a number of bacterial infections. Specifically it is used to treat strep throat, diphtheria, syphilis, and yaws. It is also used to prevent rheumatic fever. It is given by injection into a muscle. It is known as "Peanut Butter Shot" in US military slang due to its appearance.

Procaine benzylpenicillin also known as penicillin G procaine, is an antibiotic useful for the treatment of a number of bacterial infections. Specifically it is used for syphilis, anthrax, mouth infections, pneumonia, diphtheria, cellulitis, and animal bites. It is given by injection into a muscle.

ATCvet code QJ51Antibacterials for intramammary use is a therapeutic subgroup of the Anatomical Therapeutic Chemical Classification System for veterinary medicinal products, a system of alphanumeric codes developed by the World Health Organization (WHO) for the classification of drugs and other medical products for veterinary use. Subgroup QJ51 is part of the anatomical group QJ Antiinfectives for systemic use.

The side effects of penicillin are bodily responses to penicillin and closely related antibiotics that do not relate directly to its effect on bacteria. A side effect is an effect that is not intended with normal dosing. Some of these reactions are visible and some occur in the body's organs or blood. Penicillins are a widely used group of medications that are effective for the treatment of a wide variety of bacterial infections in human adults and children as well as other species. Some side effects are predictable, of which some are common but not serious, some are uncommon and serious and others are rare. The route of administration of penicillin can have an effect on the development of side effects. An example of this is irritation and inflammation that develops at a peripheral infusion site when penicillin is administered intravenously. In addition, penicillin is available in different forms. There are different penicillin medications as well as a number of β-lactam antibiotics derived from penicillin.

Meropenem/vaborbactam, sold under the brand name Vabomere among others, is a combination medication used to treat complicated urinary tract infections, complicated abdominal infections, and hospital-acquired pneumonia. It contains meropenem, a β-lactam antibiotic, and vaborbactam, a β-lactamase inhibitor. It is given by injection into a vein.

Benzathine benzylpenicillin/procaine benzylpenicillin, sold under the brand name Bicillin C-R, is an antibiotic medication. It contains the antibiotics benzathine benzylpenicillin and procaine benzylpenicillin.

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. 1 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. 1 2 3 4 5 6 7 8 Stuart MC, Kouimtzi M, Hill SR, eds. (2009). WHO Model Formulary 2008. World Health Organization. pp. 98, 105. hdl: 10665/44053 . ISBN   9789241547659.
  7. 1 2 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. 1 2 3 "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. 1 2 3 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.
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