Benzylpenicillin

Benzylpenicillin
	Penicillin G
Clinical data
Trade names	BenPen
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a685013
Pregnancy; category	AU: A; ;
Routes of; administration	Intravenous, Intramuscular, formerly used orally
ATC code	J01CE01 (WHO) S01AA14 (WHO) QJ51CE01 (WHO);
Legal status
Legal status	In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	60 %
Metabolism	hepatic
Elimination half-life	30 min
Excretion	renal
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	334.4 g/mol 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 (INN, AAN, BAN), also known as penicillin G, (USAN) is a narrow spectrum penicillin antibiotic that is given intravenously or intramuscularly as a treatment for syphilis, meningitis, endocarditis, pneumonia, lung abscesses and septicaemia in children.^[1] Penicillin G is typically given by injection parenterally, bypassing the intestines, because it is unstable in the highly acidic stomach. Because the drug is given parenterally, higher tissue concentrations of penicillin G can be achieved than is possible with phenoxymethylpenicillin. These higher concentrations translate to increased antibacterial activity.

It is on the World Health Organization's List of Essential Medicines, a list of the most important medications needed in a basic health system.^[2]

Medical uses

Specific indications for benzylpenicillin include:^[3]

Antimicrobial potency

As an antibiotic, Penicillin G is noted to possess effectiveness mainly against Gram-positive organisms. Some Gram-negative organisms such as Neisseria gonorrhoeae and Neisseria meningitidis are also reported to be susceptible to Penicillin G.^[4]

Adverse effects

Adverse effects can include hypersensitivity reactions including urticaria, fever, joint pains, rashes, angioedema, anaphylaxis, serum sickness-like reaction. Rarely CNS 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 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 renal failure, who may accumulate the drug due to reduced urinary excretion rates.^[5]^[6]

Compendial status

British Pharmacopoeia ^[7]

References

^ Rossi, S, ed. (2013). Australian Medicines Handbook (2013 ed.). Adelaide: The Australian Medicines Handbook Unit Trust. ISBN 978-0-9805790-9-3.
^ "WHO Model List of Essential Medicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
^ Rossi S, editor, ed. (2006). Australian Medicines Handbook. Adelaide: Australian Medicines Handbook. ISBN 0-9757919-2-3. {{cite book}}: |editor= has generic name (help)
^ "Penicillin G" (pdf). Toku-E. 10 October 2010. Retrieved 11 June 2012.
^ Fossieck B Jr, Parker RH. Neurotoxicity during intravenous infusion of penicillin. A review. J. Clin. Pharmacol. 14: 504- 512, 1974.
^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1195-1196.
^ British Pharmacopoeia Commission Secretariat. "Index (BP 2009)" (PDF). Retrieved 26 March 2010. {{cite web}}: Cite has empty unknown parameter: |coauthors= (help)

[AMH-1] Rossi, S, ed. (2013). Australian Medicines Handbook (2013 ed.). Adelaide: The Australian Medicines Handbook Unit Trust. ISBN 978-0-9805790-9-3.

[2] "WHO Model List of Essential Medicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.

[AMH2006-3] Rossi S, editor, ed. (2006). Australian Medicines Handbook. Adelaide: Australian Medicines Handbook. ISBN 0-9757919-2-3. {{cite book}}: |editor= has generic name (help)

[4] "Penicillin G" (pdf). Toku-E. 10 October 2010. Retrieved 11 June 2012.

[5] Fossieck B Jr, Parker RH. Neurotoxicity during intravenous infusion of penicillin. A review. J. Clin. Pharmacol. 14: 504- 512, 1974.

[6] R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 1195-1196.

[ibp2009-7] British Pharmacopoeia Commission Secretariat. "Index (BP 2009)" (PDF). Retrieved 26 March 2010. {{cite web}}: Cite has empty unknown parameter: |coauthors= (help)

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