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{{Short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
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| image = Cefprozil.svg
| image = Cefprozil.svg
<!--Clinical data-->
<!--Clinical data-->
| tradename = Cefzil
| synonyms = Cefproxil
| tradename = Cefzil, Cefproz, others
| Drugs.com = {{drugs.com|monograph|cefprozil}}
| Drugs.com = {{drugs.com|monograph|cefprozil}}
| MedlinePlus = a698022
| MedlinePlus = a698022
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<!--Chemical data-->
<!--Chemical data-->
| C=18 | H=19 | N=3 | O=5 | S=1
| C=18 | H=19 | N=3 | O=5 | S=1
| molecular_weight = 389.427 g/mol
| 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
| 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| StdInChIKey = ALYUMNAHLSSTOU-HERYOFLYSA-N
| StdInChIKey = ALYUMNAHLSSTOU-HERYOFLYSA-N
}}
}}
'''Cefprozil''' is a second-generation [[cephalosporin]] [[antibiotic]].<ref>{{Cite web|title=Cefzil (cefprozil) dosing, indications, interactions, adverse effects, and more|url=https://reference.medscape.com/drug/cefzil-cefprozil-342499|access-date=2021-05-12|website=reference.medscape.com}}</ref> Originally discovered in 1983, and approved in 1992,<ref name="Fis2006">{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=496 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA496 |language=en}}</ref> it was sold under the tradename Cefzil by [[Bristol Myers Squibb|Bristol Meyers Squibb]] until 2010 when the brand name version was discontinued.<ref>{{Cite web |date=11 September 2018 |title=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and 500 Milligrams, and for Oral Suspension, 125 Milligrams/5 Milliliters and 250 Milligrams/5 Milliliters, Were Not Withdrawn From Sale for Reasons of Safety or Effectiveness |url=https://www.federalregister.gov/d/2018-19663 |website=The Federal Register |publisher=[[National Archives]]}}</ref> It continues to be available from various companies in its generic form.<ref>{{Cite web |title=Drugs@FDA: FDA-Approved Drugs |url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm |access-date=2022-08-03 |website=www.accessdata.fda.gov}}</ref> It is used in the treatment of [[pharyngitis]], [[tonsillitis]], [[Otitis|ear infections]], [[Sinusitis|acute sinusitis]], [[Acute exacerbation of chronic obstructive pulmonary disease|bacterial exacerbation of chronic bronchitis]], and [[skin and skin structure infection]]s.<ref name=":0">{{Cite web |title=Cefzil® (CEFPROZIL) Prescribing Facts |url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/050664s026,050665s026lbl.pdf |access-date= |website=U.S. Food and Drug Administration |publisher=Bristol Myers Squibb}}</ref> It is currently available as a tablet and as a liquid [[suspension (chemistry)|suspension]].
'''Cefprozil''', sometimes spelled '''cefproxil''' and marketed under the trade name '''Cefzil,Cefproz.'''


== Adverse effects ==
'''Cefprozil''' is a second-generation [[cephalosporin]] type [[antibiotic]]. In Europe it is marketed using the trade names '''Procef''' and '''Cronocef'''.{{Citation needed|date=February 2011}} It can be used to treat [[bronchitis]], ear infections, skin infections, and other bacterial infections.{{Citation needed|date=February 2011}} It comes as a tablet and as a liquid [[suspension (chemistry)|suspension]].
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.<ref>{{cite journal | vauthors = Pichichero ME | title = Cephalosporins can be prescribed safely for penicillin-allergic patients | journal = The Journal of Family Practice | volume = 55 | issue = 2 | pages = 106–112 | date = February 2006 | pmid = 16451776 | url = http://www.jfponline.com/pdf%2F5502%2F5502JFP%5FAppliedEvidence1%2Epdf | access-date = 2011-02-26 | url-status = dead | archive-url = https://web.archive.org/web/20120916125054/http://www.jfponline.com/pdf%2F5502%2F5502JFP%5FAppliedEvidence1.pdf | archive-date = 2012-09-16 }}</ref> 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.<ref name=":0" />

Although there is a widely quoted cross-allergy risk of 10% between cephalosporins and penicillin, an article in the ''Journal of Family Practice''<ref>{{cite journal
| last1 = Pichichero | first1 = ME
| title = Cephalosporins can be prescribed safely for penicillin-allergic patients
| journal = [[J Fam Pract]]
| volume = 55
| issue = 2
| pages = 106–12
| date=February 2006
| pmid = 16451776
| url = http://www.jfponline.com/pdf%2F5502%2F5502JFP%5FAppliedEvidence1%2Epdf
}}</ref> has shown no increased risk for cross-allergy for cefprozil and several other second-generation or later cephalosporins.


==Spectrum of bacterial susceptibility and resistance==
==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.<ref>{{cite web|title=Cefprozil Susceptibility and Resistance Data|url=http://www.toku-e.com/Assets/MIC/Cefprozil.pdf|accessdate=23 July 2013}}</ref>
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.<ref>{{cite web|title=Cefprozil Susceptibility and Resistance Data|url=http://www.toku-e.com/Assets/MIC/Cefprozil.pdf|access-date=23 July 2013}}</ref>


==Synthesis==
==Synthesis==
⚫
[[File:Cefprozil synthesis.svg|thumb|center|500px|Cefprozil synthesis:<ref>H. Hoshi et al., {{Cite patent|DE|3402642}}; eidem, {{US patent|4520022}} (1984, 1985 both to [[Bristol-Myers]]).</ref><ref>{{cite journal|pmid=3624077|year=1987|author1=Naito|first1=T|title=Synthesis and structure-activity relationships of a new oral cephalosporin, BMY-28100 and related compounds|journal=The Journal of antibiotics|volume=40|issue=7|pages=991–1005|last2=Hoshi|first2=H|last3=Aburaki|first3=S|last4=Abe|first4=Y|last5=Okumura|first5=J|last6=Tomatsu|first6=K|last7=Kawaguchi|first7=H|doi=10.7164/antibiotics.40.991}}</ref> Separation of isomers:<ref> M. A. Kaplan et al., {{US patent|4727070}} (1988 to [[Bristol-Myers]]).</ref>]]
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 group|vinyl]] derivative ('''3'''); deprotection then gives cefprozil. Semisynthetic oral cephalosporin consisting of ~90:10 Z/E isomeric mixture.


⚫
[[File:Cefprozil synthesis.svg|thumb|center|500px|Cefprozil synthesis:<ref>{{cite patent | country = DE | number = 3402642 | gdate = 1984 | inventor = Hoshi H, et al. | assign1 = [[Bristol-Myers]]}}</ref><ref>{{cite patent | country = US | number = 4520022 | gdate = 1985 | inventor = Hoshi H, et al. | assign1 = [[Bristol-Myers]]}}</ref><ref>{{cite journal | vauthors = Naito T, Hoshi H, Aburaki S, Abe Y, Okumura J, Tomatsu K, Kawaguchi H | title = Synthesis and structure-activity relationships of a new oral cephalosporin, BMY-28100 and related compounds | journal = The Journal of Antibiotics | volume = 40 | issue = 7 | pages = 991–1005 | date = July 1987 | pmid = 3624077 | doi = 10.7164/antibiotics.40.991 | doi-access = free }}</ref> Separation of isomers:<ref>{{cite patent | inventor = Kaplan MA, et al. | country = US | number = 4727070 | gdate = 1988 | assign1 = [[Bristol-Myers]] }}</ref>]]
⚫
==References==
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 group|vinyl]] derivative ('''3'''); deprotection then gives cefprozil. Semisynthetic oral cephalosporin consisting of ~90:10 Z/E isomeric mixture.<ref name="TOMATSUAndo1987">{{cite journal | vauthors = Tomatsu K, Ando S, Masuyoshi S, Kondo S, Hirano M, Miyaki T, Kawaguchi H | title = In vitro and in vivo evaluations of BMY-28100, a new oral cephalosporin | journal = The Journal of Antibiotics | volume = 40 | issue = 8 | pages = 1175–1183 | date = August 1987 | pmid = 3500158 | doi = 10.7164/antibiotics.40.1175 | doi-access = free }}</ref><ref name="AlbanusBjörklund2009">{{cite journal | vauthors = Albanus L, Björklund NE, Gustafsson B, Jönsson M | title = Forty days oral toxicity of 2,6-cis-diphenylhexamethylcyclotetrasiloxane (KABI 1774)in beagle dogs with special reference to effects on the male reproductive system | journal = Acta Pharmacologica et Toxicologica | volume = 36 | issue = Suppl 3 | pages = 93–130 | year = 1975 | pmid = 1080338 | doi = 10.1111/j.1600-0773.1975.tb03087.x }}</ref>

⚫
== References ==
{{reflist}}
{{reflist}}


==External links==
== External links ==
* [http://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a698022.html Cefprozil] MedlinePlus Drug Information
* [https://www.nlm.nih.gov/medlineplus/druginfo/medmaster/a698022.html Cefprozil] MedlinePlus Drug Information


{{CephalosporinAntiBiotics}}
{{CephalosporinAntiBiotics}}


[[Category:Cephalosporin antibiotics]]
[[Category:Cephalosporin antibiotics]]
[[Category:Phenols]]
[[Category:4-Hydroxyphenyl compounds]]


{{antibiotic-stub}}
{{antibiotic-stub}}

Latest revision as of 18:38, 21 October 2024

Cefprozil
Clinical data
Trade namesCefzil, Cefproz, others
Other namesCefproxil
AHFS/Drugs.comMonograph
MedlinePlusa698022
License data
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability95%
Protein binding36%
Elimination half-life1.3 hours
Identifiers
  • 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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H19N3O5S
Molar mass389.43 g·mol−1
3D model (JSmol)
  • 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=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 checkY
  • Key:ALYUMNAHLSSTOU-HERYOFLYSA-N checkY
 ☒NcheckY (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

[edit]

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

[edit]

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

[edit]
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

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