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Revision as of 20:51, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEMBL').← Previous edit Latest revision as of 18:38, 21 October 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Phenols; added Category:4-Hydroxyphenyl compounds using HotCat 
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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 416004657 | verifiedrevid = 460024534
| IUPAC_name = 7-amino-8-oxo-3-prop-1-enyl-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid | IUPAC_name = 7-amino-8-oxo-3-prop-1-enyl-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid
| 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
Line 13: Line 14:
| legal_US = Rx-only | legal_US = Rx-only
| routes_of_administration = Oral | routes_of_administration = Oral

<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = 95% | bioavailability = 95%
| protein_bound = 36% | protein_bound = 36%
| elimination_half-life = 1.3 hours | elimination_half-life = 1.3 hours

<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 92665-29-7 | CAS_number = 92665-29-7
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| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1M698F4H4E | UNII = 1M698F4H4E
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 3506
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07651 | KEGG = D07651
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1742 --> | ChEMBL = 1742
<!--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)CS12NC(=O)(c3ccc(O)cc3)N)C(=O)O.O | smiles = O=C2N1/C(=C(/C=C/C)CS12NC(=O)(c3ccc(O)cc3)N)C(=O)O.O
| InChI = 1/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
| InChIKey = ALYUMNAHLSSTOU-CIRGZYLNBD
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
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| StdInChIKey = ALYUMNAHLSSTOU-HERYOFLYSA-N | StdInChIKey = ALYUMNAHLSSTOU-HERYOFLYSA-N
}} }}
'''Cefprozil''' is a second-generation ] ].<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 ] 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=]}}</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 ], ], ], ], ], and ]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 ].
'''Cefprozil''', sometimes spelled '''cefproxil''' and marketed under the trade name '''Cefzil''', is a second-generation ] type ]. In Europe it is marketed using the trade names '''Procef''' and '''Cronocef'''.{{Citation needed|date=February 2011}} It can be used to treat ], ear infections, skin infections, and other bacterial infections.{{Citation needed|date=February 2011}} It comes as a tablet and as a liquid ].


== Adverse effects ==
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
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" />
| last1 = Pichichero | first1 = ME
| title = Cephalosporins can be prescribed safely for penicillin-allergic patients
| journal = ]
| volume = 55
| issue = 2
| pages = 106–12
| year = 2006
| month = February
| 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==
⚫ ==References==
Currently, bacteria like '']'', '']'' and '']'' are resistant to cefprozil, while '']'' serotype Agona and ] are susceptible to cefprozil. Some bacteria like '']'', '']'' and '']'' 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==

]}}</ref><ref>{{cite patent | country = US | number = 4520022 | gdate = 1985 | inventor = Hoshi H, et al. | assign1 = ]}}</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 = ] }}</ref>]]
Displacement of the allylic chloride in intermediate ('''1''') with ] gives the phosphonium salt ('''2'''). This functionality is then converted to its ]; condensation with ] then leads to the ] 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 ==
* MedlinePlus Drug Information * MedlinePlus Drug Information


{{CephalosporinAntiBiotics}} {{CephalosporinAntiBiotics}}


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

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