Cefpodoxime: Difference between revisions

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			{{Short description\|Antibiotic}}
	{{drugbox \| verifiedrevid = 414053518
			{{Drugbox
	\|
			\| Verifiedfields = changed
	\| IUPAC_name = (6''R'',7''R'')-7-{amino}-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid
			\| verifiedrevid = 414053518
	\| image = Cefpodoxime.svg		\| image = Cefpodoxime.svg
	\| width = 200		\| width = 200
			\| alt =
	\| CASNo_Ref = {{cascite\|correct\|CAS}}

			<!--Clinical data-->
			\| tradename = Vantin, others
			\| Drugs.com = {{drugs.com\|monograph\|vantin}}
			\| MedlinePlus = a698024
			\| pregnancy_AU = B1
			\| routes_of_administration = ]

			\| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S8 -->
			\| legal_CA = Rx-only
			\| legal_CA_comment =
			\| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
			\| legal_US = Rx-only

			<!--Pharmacokinetic data-->
			\| bioavailability = 50%
			\| protein_bound = 21% to 29%
			\| metabolism = Negligible. Cefpodoxime proxetil is metabolized to cefpodoxime by the ]
			\| elimination_half-life = 2 hours
			\| excretion = ], unchanged

			<!--Identifiers-->
			\| CAS_number_Ref = {{cascite\|changed\|CAS}}
			\| CAS_number = 80210-62-4
			\| ATC_prefix = J01
			\| ATC_suffix = DD13
			\| PubChem = 6335986
			\| DrugBank_Ref = {{drugbankcite\|changed\|drugbank}}
			\| DrugBank = DB01416
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 4891496		\| ChemSpiderID = 4891496
			\| UNII_Ref = {{fdacite\|changed\|FDA}}
	\| InChI = 1/C15H17N5O6S2/c1-25-3-6-4-27-13-9(12(22)20(13)10(6)14(23)24)18-11(21)8(19-26-2)7-5-28-15(16)17-7/h5,9,13H,3-4H2,1-2H3,(H2,16,17)(H,18,21)(H,23,24)/b19-8-/t9-,13-/m1/s1
			\| UNII = 7R4F94TVGY
	\| smiles = O=C2N1/C(=C(\CS12NC(=O)C(=N\OC)/c3nc(sc3)N)COC)C(=O)O
			\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| InChIKey = WYUSVOMTXWRGEK-HBWVYFAYBO
			\| KEGG = D07650
			\| ChEBI_Ref = {{ebicite\|changed\|EBI}}
			\| ChEBI = 3504
	\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}		\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
	\| ChEMBL = 1672		\| ChEMBL = 1672
			\| synonyms = Cefpodoxime proxetil

			<!--Chemical data-->
			\| IUPAC_name = (6''R'',7''R'')-7-{amino}-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid
			\| C=15 \| H=17 \| N=5 \| O=6 \| S=2
			\| smiles = O=C2N1/C(=C(\CS12NC(=O)C(=N\OC)/c3nc(sc3)N)COC)C(=O)O
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 1S/C15H17N5O6S2/c1-25-3-6-4-27-13-9(12(22)20(13)10(6)14(23)24)18-11(21)8(19-26-2)7-5-28-15(16)17-7/h5,9,13H,3-4H2,1-2H3,(H2,16,17)(H,18,21)(H,23,24)/b19-8-/t9-,13-/m1/s1		\| StdInChI = 1S/C15H17N5O6S2/c1-25-3-6-4-27-13-9(12(22)20(13)10(6)14(23)24)18-11(21)8(19-26-2)7-5-28-15(16)17-7/h5,9,13H,3-4H2,1-2H3,(H2,16,17)(H,18,21)(H,23,24)/b19-8-/t9-,13-/m1/s1
	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = WYUSVOMTXWRGEK-HBWVYFAYSA-N		\| StdInChIKey = WYUSVOMTXWRGEK-HBWVYFAYSA-N
	\| CAS_number = 82619-04-3
	\| ATC_prefix = J01
	\| ATC_suffix = DD13
	\| PubChem = 6335986
	\| DrugBank =
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = D07650
	\| C = 15 \| H = 17 \| N = 5 \| O = 6 \| S = 2
	\| molecular_weight = 427.458 g/mol
	\| bioavailability = 50%
	\| protein_bound = 21% to 29%
	\| metabolism = Negligible. Cefpodoxime proxetil is metabolized to cefpodoxime by the ]
	\| elimination_half-life = 2 hours
	\| excretion = ], unchanged
	\| pregnancy_AU = B1
	\| pregnancy_US = B
	\| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S8 -->
	\| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
	\| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
	\| legal_US = Rx-only
	\| routes_of_administration = Oral
	}}		}}

	'''Cefpodoxime''' is an oral third generation ] ]. ~~It is marketed as the ] '''cefpodoxime proxetil''' by ] under the trade name '''Vantin''' and under the name '''Orelox''' by ; '''PECEF'''~~ in Dr ~~Reddy's~~ ~~(Farhaad)]~~. It is active against ~~most~~ ] and ] organisms. ~~Notable~~ exceptions ~~include~~ '']'', '']'', and '']''. It is ~~commonly~~ used to treat acute ], ], ~~and~~ ]. It also finds use as oral continuation therapy when ] cephalosporins (such as ]) are no longer necessary for continued treatment.		'''Cefpodoxime''' is an oral, third-generation ] ] available in various generic preparations. It is active against both ] and ] organisms with notable exceptions including '']'', '']'', and '']''. It is typically used to treat acute ], ], ], and gonorrhea. It also finds use as oral continuation therapy when ] cephalosporins (such as ]) are no longer necessary for continued treatment.

			Cefpodoxime inhibits peptidoglycan synthesis in bacterial cell walls. It has an oral ] of approximately 50%, which is increased when taken with food. It has an elimination half-life of 2-3 hours in adults, which is prolonged in renal failure. Approved indications include community acquired pneumonia, uncomplicated skin and skin structure infections, and uncomplicated urinary tract infections.
	], the parent company of ], markets cefpodoxime proxetil under the trade name '''Simplicef''' for veterinary use. The dose range in dogs is 5–10 mg/kg body weight, administered orally, once a day.

			<!-- Society and culture -->
	] of cefpodoxime '''proxetil''']]{{clear-left}}
			It was patented in 1980 and approved for medical use in 1989.<ref name=Fis2006>{{cite book \| vauthors = Fischer J, Ganellin CR \|title=Analogue-based Drug Discovery \|date=2006 \|publisher=John Wiley & Sons \|isbn=9783527607495 \|page=495 \|url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA495 \|language=en}}</ref>

			==Spectrum of bacterial susceptibility and resistance==
			Cefpodoxime has been used to treat gonorrhoea, tonsillitis, pneumonia, and bronchitis. The following minimum inhibitory concentrations have been reported:<ref>{{cite web \| title = Cefpodoxime, Free Acid Susceptibility and Minimum Inhibitory Concentration (MIC) Data \| url = http://www.toku-e.com/Assets/MIC/Cefpodoxime%20Free%20acid.pdf }}</ref>

			* '']'': ≤0.03 – 1 μg/ml
			* ''Neisseria gonorrhoeae'': 0.004 – 0.06 μg/ml
			* ''Streptococcus pyogenes'': ≤0.004 – 2 μg/ml

			==Brand names==
			] markets cefpodoxime proxetil under the trade name <!-- (C-doxim 50Dt,drysyp,100Dt/drysyp,200 and Cv200by Neomed(India) --> Simplicef for veterinary use, and Finecure in ] markets the drug as Cefpo.<ref>{{Cite web\|url=http://www.finecurepharma.com/\|title=Pharmaceuticals Manufacturer, Marketer, Pharmaceutical Manufacturing Company India\|website=www.finecurepharma.com\|access-date=2019-05-26}}</ref><!-- (Cefpo 100Dt, 200, Cv and Dry Syrup) --><ref>{{cite web \|title=Anti Biotics and Anti Bacterial \|url=http://www.finecurepharma.com/cephalosporins.htm#cefu5 \|publisher=Finecurepharmaceuticalsltd \|access-date=2012-03-27 \|archive-url=https://web.archive.org/web/20120306080133/http://www.finecurepharma.com/cephalosporins.htm#cefu5 \|archive-date=2012-03-06 \|url-status=dead }}</ref>

			Vantin (by ])<ref>{{Cite web\|title = Vantin – Drugs.com\|url = https://www.drugs.com/international/vantin.html\|website = www.drugs.com\|access-date = 2019-05-02}}</ref> in suspension or tablet form.

			Toraxim (by Delta Pharma Ltd., ])

			Trucef (by ], Bangladesh)

			Tricef (by ], ])

			Orelox (by ])<ref>{{Cite web\|title = Orelox – Drugs.com\|url = https://www.drugs.com/international/orelox.html\|website = www.drugs.com\|access-date = 2015-11-28}}</ref>

			MAPDOX-CV: Combination cefpodoxime–clavulanic acid{{By whom\|date=January 2025\|reason=Marketer not given.}}

			MONOTAX O (cefpodoxime)/MONOTAX CV (cefpodoxime–clavulanic acid) by ]

			ACXIME 200/CV (by Allencia Biosciences, India)

			POSTPOD-50 (cefpodoxime 50mg/5ml) by Laafon Galaxy Pharmaceuticals<ref>{{Cite web\|title=Postpod dry syrup\|url=https://www.laafon.com/product/postpod-dry-syrup/\|access-date=2020-09-16\|website=Laafon Galaxy Pharmaceuticals Company in Karnal\|language=en-US}}</ref>

			==References==
			<references />

	== External links ==		== External links ==
	* {{PubChem\|6526396}} - cefpodoxime proxetil		* {{PubChem\|6526396}} – cefpodoxime proxetil
	* (from manufacturer's website)		* (from manufacturer's website)
	* (from manufacturer's website)		* (from manufacturer's website)
			*

	{{CephalosporinAntiBiotics}}		{{CephalosporinAntiBiotics}}

	]		]
	]		]
	]		]

	{{antibiotic-stub}}

	]
	]
	]
	]

Latest revision as of 01:14, 7 January 2025

Antibiotic Pharmaceutical compound

Cefpodoxime
Clinical data

Trade names	Vantin, others
Other names	Cefpodoxime proxetil
AHFS/Drugs.com	Monograph
MedlinePlus	a698024
Pregnancy category	AU: B1
Routes of administration	By mouth
ATC code	J01DD13 (WHO)
Legal status
Legal status	CA: ℞-only US: ℞-only
Pharmacokinetic data
Bioavailability	50%
Protein binding	21% to 29%
Metabolism	Negligible. Cefpodoxime proxetil is metabolized to cefpodoxime by the liver
Elimination half-life	2 hours
Excretion	Kidney, unchanged
Identifiers
IUPAC name (6R,7R)-7-{amino}-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid
CAS Number	80210-62-4
PubChem CID	6335986
DrugBank	DB01416
ChemSpider	4891496
UNII	7R4F94TVGY
KEGG	D07650
ChEBI	CHEBI:3504
ChEMBL	ChEMBL1672
CompTox Dashboard (EPA)	DTXSID6022765
ECHA InfoCard	100.210.871
Chemical and physical data
Formula	C₁₅H₁₇N₅O₆S₂
Molar mass	427.45 g·mol
3D model (JSmol)	Interactive image
SMILES O=C2N1/C(=C(\CS12NC(=O)C(=N\OC)/c3nc(sc3)N)COC)C(=O)O
InChI InChI=1S/C15H17N5O6S2/c1-25-3-6-4-27-13-9(12(22)20(13)10(6)14(23)24)18-11(21)8(19-26-2)7-5-28-15(16)17-7/h5,9,13H,3-4H2,1-2H3,(H2,16,17)(H,18,21)(H,23,24)/b19-8-/t9-,13-/m1/s1 Key:WYUSVOMTXWRGEK-HBWVYFAYSA-N
(what is this?) (verify)

Cefpodoxime is an oral, third-generation cephalosporin antibiotic available in various generic preparations. It is active against both Gram-positive and Gram-negative organisms with notable exceptions including Pseudomonas aeruginosa, Enterococcus, and Bacteroides fragilis. It is typically used to treat acute otitis media, pharyngitis, sinusitis, and gonorrhea. It also finds use as oral continuation therapy when intravenous cephalosporins (such as ceftriaxone) are no longer necessary for continued treatment.

Cefpodoxime inhibits peptidoglycan synthesis in bacterial cell walls. It has an oral bioavailability of approximately 50%, which is increased when taken with food. It has an elimination half-life of 2-3 hours in adults, which is prolonged in renal failure. Approved indications include community acquired pneumonia, uncomplicated skin and skin structure infections, and uncomplicated urinary tract infections.

It was patented in 1980 and approved for medical use in 1989.

Spectrum of bacterial susceptibility and resistance

Cefpodoxime has been used to treat gonorrhoea, tonsillitis, pneumonia, and bronchitis. The following minimum inhibitory concentrations have been reported:

Haemophilus influenzae: ≤0.03 – 1 μg/ml
Neisseria gonorrhoeae: 0.004 – 0.06 μg/ml
Streptococcus pyogenes: ≤0.004 – 2 μg/ml

Brand names

Zoetis markets cefpodoxime proxetil under the trade name Simplicef for veterinary use, and Finecure in India markets the drug as Cefpo.

Vantin (by Pfizer) in suspension or tablet form.

Toraxim (by Delta Pharma Ltd., Bangladesh)

Trucef (by Renata Limited, Bangladesh)

Tricef (by Alkaloid Skopje, North Macedonia)

Orelox (by Sanofi-Aventis)

MAPDOX-CV: Combination cefpodoxime–clavulanic acid

MONOTAX O (cefpodoxime)/MONOTAX CV (cefpodoxime–clavulanic acid) by Zydus Healthcare Ltd.

ACXIME 200/CV (by Allencia Biosciences, India)

POSTPOD-50 (cefpodoxime 50mg/5ml) by Laafon Galaxy Pharmaceuticals

References

Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 495. ISBN 9783527607495.
"Cefpodoxime, Free Acid Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF).
"Pharmaceuticals Manufacturer, Marketer, Pharmaceutical Manufacturing Company India". www.finecurepharma.com. Retrieved 2019-05-26.
"Anti Biotics and Anti Bacterial". Finecurepharmaceuticalsltd. Archived from the original on 2012-03-06. Retrieved 2012-03-27.
"Vantin – Drugs.com". www.drugs.com. Retrieved 2019-05-02.
"Orelox – Drugs.com". www.drugs.com. Retrieved 2015-11-28.
"Postpod dry syrup". Laafon Galaxy Pharmaceuticals Company in Karnal. Retrieved 2020-09-16.

External links

CID 6526396 from PubChem – cefpodoxime proxetil
Vantin Tablets and Oral Suspension Torpod (Torrent) Full U.S. Prescribing Information (from manufacturer's website)
Simplicef (from manufacturer's website)
Intas Pharmaceuticals Ltd. » Animal Health :: Intas - a leading global pharmaceutical formulation development, manufacturing and marketing company

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)	Benzylpenicillin (G) Benzathine benzylpenicillin Procaine benzylpenicillin Phenoxymethylpenicillin (V) Propicillin Pheneticillin Azidocillin Clometocillin Penamecillin
β-lactamase resistant (2nd generation)	Cloxacillin (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin

Extended
spectrum

Aminopenicillins (3rd generation)	Amoxicillin Ampicillin (Pivampicillin Hetacillin Bacampicillin Lenampicillin Metampicillin Talampicillin) Epicillin
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin / Carindacillin Temocillin
Ureidopenicillins (4th generation)	Piperacillin Azlocillin Mezlocillin
Other	Mecillinam (Pivmecillinam) Sulbenicillin

Carbapenems / Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin Cefalexin Cefadroxil Cefapirin Cefazedone Cefazaflur Cefradine Cefroxadine Ceftezole Cefaloglycin Cefacetrile Cefalonium Cefaloridine Cefalotin Cefatrizine
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole Cefonicid Ceforanide Cefuzonam Cephamycin (Cefoxitin Cefotetan Cefminox Cefbuperazone Cefmetazole) Carbacephem (Loracarbef)
3rd generation	Cefixime Ceftriaxone Cefotaxime Antipseudomonal (Ceftazidime Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam Cefetamet Cefodizime Cefpimizole Cefsulodin Cefteram Ceftiolene Oxacephem (Flomoxef Latamoxef)
4th generation	Cefepime Cefozopran Cefpirome Cefquinome
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking: Ramoplanin

Intracellular

Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Other

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

Categories: