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==Synthesis==
==Synthesis==
Note: Picture here is slight innaccuracy but this was from Lednicer book.
[[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 | url = https://www.jstage.jst.go.jp/article/antibiotics1968/40/7/40_7_991/_pdf }}</ref> Separation of isomers:<ref>{{cite patent | inventor = Kaplan MA, et al. | country = US | number = 4727070 | gdate = 1988 | assign1 = [[Bristol-Myers]] }}</ref>]]
[[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 | url = https://www.jstage.jst.go.jp/article/antibiotics1968/40/7/40_7_991/_pdf }}</ref> Separation of isomers:<ref>{{cite patent | inventor = Kaplan MA, et al. | country = US | number = 4727070 | gdate = 1988 | assign1 = [[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.
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.

Revision as of 09:56, 8 March 2020

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 mass389.427 g/mol 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. It can be used to treat ear infections, skin infections, and other bacterial infections.[citation needed] It comes as a tablet and as a liquid suspension.

Although there is a widely quoted cross-allergy risk of 10% between cephalosporins and penicillin, an article[1] has shown no increased risk for cross-allergy for cefprozil and several other second-generation or later cephalosporins.

It was patented in 1983 and approved for medical use in 1992.[2]

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.[3]

Synthesis

Note: Picture here is slight innaccuracy but this was from Lednicer book.

Cefprozil synthesis:[4][5][6] Separation of isomers:[7]

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.

Brand names

It is marketed under the trade names Cefzil and Cefproz. In Europe it is marketed using the trade names Procef and Cronocef.[citation needed]

References

  1. ^ Pichichero ME (February 2006). "Cephalosporins can be prescribed safely for penicillin-allergic patients" (PDF). The Journal of Family Practice. 55 (2): 106–12. PMID 16451776. Archived from the original on 2012-09-16. Retrieved 2011-02-26.
  2. ^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 496. ISBN 9783527607495. {{cite book}}: Unknown parameter |name-list-format= ignored (|name-list-style= suggested) (help)
  3. ^ "Cefprozil Susceptibility and Resistance Data" (PDF). Retrieved 23 July 2013.
  4. ^ DE 3402642, Hoshi H, et al., issued 1984, assigned to Bristol-Myers 
  5. ^ US 4520022, Hoshi H, et al., issued 1985, assigned to Bristol-Myers 
  6. ^ 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.
  7. ^ US 4727070, Kaplan MA, et al., issued 1988, assigned to Bristol-Myers 
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