Misplaced Pages

Cefprozil: Difference between revisions

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Browse history interactively← Previous editContent deleted Content addedVisualWikitext
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 
(59 intermediate revisions by 40 users not shown)
Line 1: Line 1:
{{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
Line 32: Line 30:
| 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
Line 46: Line 44:
| 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}}


] ]
] ]


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

]
]
]
]
]

Latest revision as of 18:38, 21 October 2024

Chemical compound Pharmaceutical compound
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
IUPAC name
  • 7-amino-8-oxo-3-prop-1-enyl-5-thia-1-azabicyclooct-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
3D model (JSmol)
SMILES
  • O=C2N1/C(=C(/C=C/C)CS12NC(=O)(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. Originally discovered in 1983, and approved in 1992, it was sold under the tradename Cefzil by Bristol Meyers Squibb until 2010 when the brand name version was discontinued. It continues to be available from various companies in its generic form. It is used in the treatment of pharyngitis, tonsillitis, ear infections, acute sinusitis, bacterial exacerbation of chronic bronchitis, and skin and skin structure infections. 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. 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.

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.

Synthesis

Cefprozil synthesis: Separation of isomers:

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.

References

  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. ^ "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.

External links

Antibacterials active on the cell wall and envelope (J01C-J01D)
β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)
Penicillins (Penams)
Narrow
spectrum
β-lactamase sensitive
(1st generation)
β-lactamase resistant
(2nd generation)
Extended
spectrum
Aminopenicillins (3rd generation)
Carboxypenicillins (4th generation)
Ureidopenicillins (4th generation)
Other
Carbapenems / Penems
Cephems
Cephalosporins
Cephamycins
Carbacephems
1st generation
2nd generation
3rd generation
4th generation
5th generation
Siderophore
Veterinary
Monobactams
β-lactamase inhibitors
Combinations
Polypeptides
Lipopeptides
Other
  • Inhibits PG elongation and crosslinking: Ramoplanin
Intracellular
Other
Stub icon

This systemic antibiotic-related article is a stub. You can help Misplaced Pages by expanding it.

Categories: