Cefprozil

Cefprozil
Clinical data
Trade names	Cefzil, Cefproz, others
Other names	Cefproxil
AHFS/Drugs.com	Monograph
MedlinePlus	a698022
License data	US FDA: Cefprozil;
Routes of; administration	Oral
ATC code	J01DC10 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Bioavailability	95%
Protein binding	36%
Elimination half-life	1.3 hours
Identifiers
	IUPAC name 7-[2-amino-2-(4-hydroxyphenyl)-acetyl]amino-8-oxo-3-prop-1-enyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;
CAS Number	92665-29-7 ;
PubChem CID	9887643;
DrugBank	DB01150 ;
ChemSpider	8063315 ;
UNII	1M698F4H4E;
KEGG	D07651 ;
ChEBI	CHEBI:3506 ;
ChEMBL	ChEMBL1742 ;
CompTox Dashboard (EPA)	DTXSID10873545 ;
Chemical and physical data
Formula	C18H19N3O5S
Molar mass	389.43 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2N1/C(=C(/C=C/C)CS[C@@H]1[C@@H]2NC(=O)[C@@H](c3ccc(O)cc3)N)C(=O)O.O;
	InChI InChI=1S/C18H19N3O5S.H2O/c1-2-3-10-8-27-17-13(16(24)21(17)14(10)18(25)26)20-15(23)12(19)9-4-6-11(22)7-5-9;/h2-7,12-13,17,22H,8,19H2,1H3,(H,20,23)(H,25,26);1H2/b3-2-;/t12-,13-,17-;/m1./s1 ; Key:ALYUMNAHLSSTOU-HERYOFLYSA-N ;
	(what is this?) (verify)

Cefprozil is a second-generation cephalosporin antibiotic.^[1] Originally discovered in 1983, and approved in 1992,^[2] it was sold under the tradename Cefzil by Bristol Meyers Squibb until 2010 when the brand name version was discontinued.^[3] It continues to be available from various companies in its generic form.^[4] It is used in the treatment of pharyngitis, tonsillitis, ear infections, acute sinusitis, bacterial exacerbation of chronic bronchitis, and skin and skin structure infections.^[5] It is currently available as a tablet and as a liquid suspension.

Adverse effects

Although there is a widely quoted cross-allergy risk of 10% between cephalosporins and penicillin, research has shown no increased risk for cross-allergy for cefprozil and several other second-generation or later cephalosporins.^[6] The most common side effects were increased hepatic lab values (including AST and ALGT), dizziness, eosinophilia, diaper rash and superinfection, genital pruritus, vaginitis, diarrhea, nausea, vomiting, and abdominal pain.^[5]

Spectrum of bacterial susceptibility and resistance

Currently, bacteria like Enterobacter aerogenes, Morganella morganii and Pseudomonas aeruginosa are resistant to cefprozil, while Salmonella enterica serotype Agona and streptococci are susceptible to cefprozil. Some bacteria like Brucella abortus, Moraxella catarrhalis and Streptococcus pneumoniae have developed resistance towards cefprozil in varying degrees. Detailed minimum inhibition concentration information is given by the Cefprozil Susceptibility and Resistance Data sheet.^[7]

Synthesis

Cefprozil synthesis:^[8]^[9]^[10] Separation of isomers:^[11]

Displacement of the allylic chloride in intermediate (1) with triphenylphosphine gives the phosphonium salt (2). This functionality is then converted to its ylide; condensation with acetaldehyde then leads to the vinyl derivative (3); deprotection then gives cefprozil. Semisynthetic oral cephalosporin consisting of ~90:10 Z/E isomeric mixture.^[12]^[13]

References

^ "Cefzil (cefprozil) dosing, indications, interactions, adverse effects, and more". reference.medscape.com. Retrieved 2021-05-12.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 496. ISBN 9783527607495.
^ "Determination That CEFZIL (Cefprozil) Tablets, 250 Milligrams and 500 Milligrams, and for Oral Suspension, 125 Milligrams/5 Milliliters and 250 Milligrams/5 Milliliters, Were Not Withdrawn From Sale for Reasons of Safety or Effectiveness". The Federal Register. National Archives. 11 September 2018.
^ "Drugs@FDA: FDA-Approved Drugs". www.accessdata.fda.gov. Retrieved 2022-08-03.
^ ^a ^b "Cefzil® (CEFPROZIL) Prescribing Facts" (PDF). U.S. Food and Drug Administration. Bristol Myers Squibb.
^ Pichichero ME (February 2006). "Cephalosporins can be prescribed safely for penicillin-allergic patients" (PDF). The Journal of Family Practice. 55 (2): 106–112. PMID 16451776. Archived from the original on 2012-09-16. Retrieved 2011-02-26.
^ "Cefprozil Susceptibility and Resistance Data" (PDF). Retrieved 23 July 2013.
^ DE 3402642, Hoshi H, et al., issued 1984, assigned to Bristol-Myers
^ US 4520022, Hoshi H, et al., issued 1985, assigned to Bristol-Myers
^ Naito T, Hoshi H, Aburaki S, Abe Y, Okumura J, Tomatsu K, Kawaguchi H (July 1987). "Synthesis and structure-activity relationships of a new oral cephalosporin, BMY-28100 and related compounds". The Journal of Antibiotics. 40 (7): 991–1005. doi:10.7164/antibiotics.40.991. PMID 3624077.
^ US 4727070, Kaplan MA, et al., issued 1988, assigned to Bristol-Myers
^ Tomatsu K, Ando S, Masuyoshi S, Kondo S, Hirano M, Miyaki T, Kawaguchi H (August 1987). "In vitro and in vivo evaluations of BMY-28100, a new oral cephalosporin". The Journal of Antibiotics. 40 (8): 1175–1183. doi:10.7164/antibiotics.40.1175. PMID 3500158.
^ Albanus L, Björklund NE, Gustafsson B, Jönsson M (1975). "Forty days oral toxicity of 2,6-cis-diphenylhexamethylcyclotetrasiloxane (KABI 1774)in beagle dogs with special reference to effects on the male reproductive system". Acta Pharmacologica et Toxicologica. 36 (Suppl 3): 93–130. doi:10.1111/j.1600-0773.1975.tb03087.x. PMID 1080338.

External links

Cefprozil MedlinePlus Drug Information

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[1] "Cefzil (cefprozil) dosing, indications, interactions, adverse effects, and more". reference.medscape.com. Retrieved 2021-05-12.

[Fis2006-2] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 496. ISBN 9783527607495.

[3] "Determination That CEFZIL (Cefprozil) Tablets, 250 Milligrams and 500 Milligrams, and for Oral Suspension, 125 Milligrams/5 Milliliters and 250 Milligrams/5 Milliliters, Were Not Withdrawn From Sale for Reasons of Safety or Effectiveness". The Federal Register. National Archives. 11 September 2018.

[4] "Drugs@FDA: FDA-Approved Drugs". www.accessdata.fda.gov. Retrieved 2022-08-03.

[:0-5] "Cefzil® (CEFPROZIL) Prescribing Facts" (PDF). U.S. Food and Drug Administration. Bristol Myers Squibb.

[6] Pichichero ME (February 2006). "Cephalosporins can be prescribed safely for penicillin-allergic patients" (PDF). The Journal of Family Practice. 55 (2): 106–112. PMID 16451776. Archived from the original on 2012-09-16. Retrieved 2011-02-26.

[7] "Cefprozil Susceptibility and Resistance Data" (PDF). Retrieved 23 July 2013.

[8] DE 3402642, Hoshi H, et al., issued 1984, assigned to Bristol-Myers

[9] US 4520022, Hoshi H, et al., issued 1985, assigned to Bristol-Myers

[10] Naito T, Hoshi H, Aburaki S, Abe Y, Okumura J, Tomatsu K, Kawaguchi H (July 1987). "Synthesis and structure-activity relationships of a new oral cephalosporin, BMY-28100 and related compounds". The Journal of Antibiotics. 40 (7): 991–1005. doi:10.7164/antibiotics.40.991. PMID 3624077.

[11] US 4727070, Kaplan MA, et al., issued 1988, assigned to Bristol-Myers

[TOMATSUAndo1987-12] Tomatsu K, Ando S, Masuyoshi S, Kondo S, Hirano M, Miyaki T, Kawaguchi H (August 1987). "In vitro and in vivo evaluations of BMY-28100, a new oral cephalosporin". The Journal of Antibiotics. 40 (8): 1175–1183. doi:10.7164/antibiotics.40.1175. PMID 3500158.

[AlbanusBjörklund2009-13] Albanus L, Björklund NE, Gustafsson B, Jönsson M (1975). "Forty days oral toxicity of 2,6-cis-diphenylhexamethylcyclotetrasiloxane (KABI 1774)in beagle dogs with special reference to effects on the male reproductive system". Acta Pharmacologica et Toxicologica. 36 (Suppl 3): 93–130. doi:10.1111/j.1600-0773.1975.tb03087.x. PMID 1080338.

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