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Revision as of 20:41, 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').← Previous edit Latest revision as of 16:22, 11 November 2024 edit undoMuhammad Anas Sidik (talk | contribs)293 editsNo edit summaryTags: Mobile edit Mobile web edit 
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{{Short description|A third generation cephalosporin antibiotic}}
{{Drugbox
{{Use dmy dates|date=April 2024}}
| verifiedrevid = 443508903
{{cs1 config|name-list-style=vanc|display-authors=6}}
| IUPAC_name = (6''R'',7''R'')-7-{amino}-3-ethenyl-8-oxo-5-thia-<br>1-azabicyclooct-2-ene-2-carboxylic acid
{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 460023156
| image = Cefixime.svg | image = Cefixime.svg
| width =
| alt =
| caption =


<!--Clinical data--> <!-- Clinical data -->
| pronounce =
| tradename = Suprax
| tradename = Suprax, others<ref name=genericnames/>
| Drugs.com = {{drugs.com|monograph|cefixime}} | Drugs.com = {{drugs.com|monograph|cefixime}}
| MedlinePlus = a690007 | MedlinePlus = a690007
| DailyMedID = Cefixime
| pregnancy_category = B
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| legal_status =
| pregnancy_AU_comment =
| routes_of_administration = Oral
| pregnancy_category =
| routes_of_administration = ]
| class =
| ATC_prefix = J01
| ATC_suffix = DD08
| ATC_supplemental =

<!-- Legal status -->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_AU_comment =
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F-->
| legal_BR_comment =
| legal_CA = Rx-only
| legal_CA_comment = <ref>{{cite web | title=Antibiotics | website=] | date=8 May 2018 | url=https://www.canada.ca/en/services/health/drug-health-products/drug-medical-device-highlights-2017/approved-drugs/antibiotics.html | access-date=13 April 2024}}</ref><ref>{{cite web | title=Regulatory Decision Summary for Auro-Cefixime | website=Drug and Health Products Portal | date=9 November 2016 | url=https://dhpp.hpfb-dgpsa.ca/review-documents/resource/RDS00339 | access-date=13 April 2024}}</ref>
| legal_DE = <!-- Anlage I, II, III or Unscheduled-->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = POM
| legal_UK_comment = <ref name="Suprax SmPC">{{cite web | title=Suprax 200 mg Tablets - Summary of Product Characteristics (SmPC) | website=(emc) | date=20 August 2019 | url=https://www.medicines.org.uk/emc/product/5534/smpc | access-date=23 April 2020 | archive-date=22 September 2020 | archive-url=https://web.archive.org/web/20200922195438/https://www.medicines.org.uk/emc/product/5534/smpc | url-status=dead }}</ref>
| legal_US = Rx-only
| legal_US_comment =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_UN_comment =
| legal_status = Rx-only


<!--Pharmacokinetic data--> <!-- Pharmacokinetic data -->
| bioavailability = 40% to 50% | bioavailability = 30 to 50%<ref name=AHFS2016/>
| protein_bound = Approximately 60% | protein_bound = Approximately 60%
| metabolism = | metabolism =
| metabolites =
| elimination_half-life = Variable<br>Average 3 to 4 hours
| onset =
| excretion = ] and biliary
| elimination_half-life = Variable<br />Average 3 to 4 hours
| duration_of_action =
| excretion = ] and biliary


<!--Identifiers--> <!-- Identifiers -->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 79350-37-1 | CAS_number = 79350-37-1
| CAS_supplemental =
| ATC_prefix = J01
| ATC_suffix = DD08
| ATC_supplemental =
| PubChem = 5362065 | PubChem = 5362065
| IUPHAR_ligand =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00671 | DrugBank = DB00671
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4514923 | ChemSpiderID = 4514923
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 97I1C92E55 | UNII = XZ7BG04GJX
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00258 | KEGG = D00258
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| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1541 | ChEMBL = 1541
| NIAID_ChemDB =
| PDB_ligand =
| synonyms =


<!--Chemical data--> <!-- Chemical and physical data -->
| IUPAC_name = (6''R'',7''R'')-7-{amino}-3-ethenyl-8-oxo-5-thia-1-azabicyclooct-2-ene-2-carboxylic acid
| C=16 | H=15 | N=5 | O=7 | S=2
| C=16 | H=15 | N=5 | O=7 | S=2
| molecular_weight = 453.452 g/mol
| smiles = O=C2N1/C(=C(/C=C)CS12NC(=O)C(=N\OCC(=O)O)/c3nc(sc3)N)C(=O)O | SMILES = O=C2N1/C(=C(/C=C)CS12NC(=O)C(=N\OCC(=O)O)/c3nc(sc3)N)C(=O)O
| Jmol =
| InChI = 1/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9-/t10-,14-/m1/s1
| InChIKey = OKBVVJOGVLARMR-QSWIMTSFBM
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9-/t10-,14-/m1/s1 | StdInChI = 1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9-/t10-,14-/m1/s1
| StdInChI_comment =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OKBVVJOGVLARMR-QSWIMTSFSA-N | StdInChIKey = OKBVVJOGVLARMR-QSWIMTSFSA-N
| density =
| density_notes =
| melting_point =
| melting_high =
| melting_notes =
| boiling_point =
| boiling_notes =
| solubility =
| sol_units =
| specific_rotation =
}} }}
'''Cefixime''' is an oral third generation ] ]. Cefixime is a cephalosporin antibiotic used to treat infections caused by bacteria such as pneumonia; bronchitis; gonorrhea; and ear, lung, throat, and urinary tract infections. Antibiotics will not work for colds, flu, or other viral infections.


<!-- Definition and medical uses -->
It was sold under the trade name '''Suprax''' in the USA until 2003 when it was taken off the market by drug manufacturer ] after its ] expired. The oral suspension form of "Suprax" was re-launched by Lupin in the USA.
'''Cefixime''', sold under the brand name '''Suprax''' among others, is an ] medication used to treat a number of ].<ref name=AHFS2016/> These infections include ], ], ], ], ], and ].<ref name=AHFS2016/> For gonorrhea typically only one dose is required.<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 9789241547659 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | page=107 | publisher = World Health Organization | hdl-access=free }}</ref> In the United States it is a second-line treatment to ] for gonorrhea.<ref name=AHFS2016/> It is taken by mouth.<ref name=AHFS2016/>


<!-- Side effects and mechanism -->
Cefixime API is manufactured by many pharmaceutical companies the world over. The major manufacturers are based in India.
Common side effects include ], ], and ].<ref name=AHFS2016/> Serious side effects may include ]s and ].<ref name=AHFS2016/> It is not recommended in people with a history of a severe ].<ref name=WHO2008/><!-- Quote = sensitivity to Beta Lactam antibacterials (avoid if history of immediate hypersensitivity reaction --> It appears to be relatively safe during ].<ref name="Drugs.com pregnancy">{{cite web | title=Cefixime (Suprax) Use During Pregnancy | website=Drugs.com | date=29 March 2019 | url=https://www.drugs.com/pregnancy/cefixime.html | access-date=24 December 2019}}</ref> It is in the ] class of medications.<ref name=AHFS2016/> It works by disrupting the bacteria's ] resulting in its death.<ref name=AHFS2016>{{cite web|title=Cefixime|url=https://www.drugs.com/monograph/cefixime.html|publisher=The American Society of Health—System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161127220806/https://www.drugs.com/monograph/cefixime.html|archive-date=27 November 2016}}</ref>


<!-- Society and culture -->
Cefixime was patented in 1979 and approved for medical use in the United States in 1989.<ref name=AHFS2016/><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 }}</ref> It is on the ].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> It is available as a ] in the United States.<ref>{{cite web | title=Generic Suprax Availability | website=Drugs.com | url=https://www.drugs.com/availability/generic-suprax.html | access-date=23 April 2020}}</ref>


==References== ==Medical uses==

<References/>
Cefixime treats infections of the:
http://www.nlm.nih.gov/medlineplus/druginfo/meds/a690007.html
* Urinary tract: Uncomplicated urinary tract infections caused by susceptible isolates of '']'' and '']''.<ref name="Suprax FDA label" /><ref name="Suprax SmPC" /><ref name=AHFS2016/>
{{CephalosporinAntiBiotics}}
* Ear: ] caused by '']'', '']'' and '']''.<ref name="Suprax FDA label" /><ref name="Suprax SmPC" /><ref name=AHFS2016/>
* Throat: Tonsillitis and pharyngitis caused by '']''.<ref name="Suprax FDA label" /><ref name="Suprax SmPC" /><ref name=AHFS2016/>
* Chest and lungs: Chronic bronchitis caused by ''] ''and '']''.<ref name="Suprax FDA label" /><ref name="Suprax SmPC" /><ref name=AHFS2016/>
* Cervix and urethra: Gonorrhea (cervical/urethral) caused by susceptible isolates of ''Neisseria gonorrhoeae'' (penicillinase-and non-penicillinase-producing isolates).<ref name="Suprax FDA label" /><ref name="Suprax SmPC" /><ref name=AHFS2016/>
*Skin and soft tissue infection: effective against group A and B beta-hemolytic streptococci. However, Staphylococcus aureus, coagulase-negative staphylococci and enterococci are resistant.<ref name=":0">{{Cite book|url=https://www.worldcat.org/oclc/1011357224|title=Kucers' the use of antibiotics : a clinical review of antibacterial, antifungal, antiparasitic and antiviral drugs|date=2017| vauthors = Grayson ML |isbn=978-1-315-15211-0|edition=Seventh|location=Boca Raton|oclc=1011357224}}</ref>

It is also used to treat ].<ref>{{cite journal | vauthors = Matsumoto Y, Ikemoto A, Wakai Y, Ikeda F, Tawara S, Matsumoto K | title = Mechanism of therapeutic effectiveness of cefixime against typhoid fever | journal = Antimicrobial Agents and Chemotherapy | volume = 45 | issue = 9 | pages = 2450–2454 | date = September 2001 | pmid = 11502513 | pmc = 90676 | doi = 10.1128/aac.45.9.2450-2454.2001 }}</ref><ref>{{cite journal | vauthors = Bhutta ZA, Khan IA, Molla AM | title = Therapy of multidrug-resistant typhoid fever with oral cefixime vs. intravenous ceftriaxone | journal = The Pediatric Infectious Disease Journal | volume = 13 | issue = 11 | pages = 990–994 | date = November 1994 | pmid = 7845753 | doi = 10.1097/00006454-199411000-00010 }}</ref><ref name=AHFS2016/>

===Spectrum of bacterial susceptibility===
Cefixime is a broad spectrum cephalosporin antibiotic and is commonly used to treat bacterial infections of the ear, urinary tract, and upper respiratory tract. The following represents MIC susceptibility data for a few medically significant microorganisms:<ref>{{cite web | title = Cefixime trihydrate Susceptibility and Minimum Inhibitory Concentration (MIC) Data | work = www.toku-e.com | url = http://www.toku-e.com/Assets/MIC/Cefixime%20trihydrate.pdf }}</ref>
* ''Escherichia coli'': 0.015&nbsp;μg/mL – 4&nbsp;μg/mL
* ''Haemophilus influenzae'': ≤0.004&nbsp;μg/mL – >4&nbsp;μg/mL
* ''Proteus mirabilis'': ≤0.008&nbsp;μg/mL – 0.06&nbsp;μg/mL
* Streptococcus pneumoniae: 0.12&nbsp;μg/mL<ref name=":0" />
* Staphylococcus aureus: >128&nbsp;μg/mL (Resistant)<ref name=":0"/>
* Enterobacter spp.: >128&nbsp;μg/mL (Resistant) <ref name=":0"/>

==Mechanism of action==

The bactericidal action of Cefixime is due to the inhibition of cell wall synthesis.{{medcn|date=August 2023}} It binds to one of the ] (PBPs) which inhibits the final transpeptidation step of the peptidoglycan synthesis in the bacterial cell wall, thus inhibiting biosynthesis and arresting cell wall assembly resulting in bacterial cell death.{{medcn|date=August 2023}}

''Absorption''
Only 40–50% is absorbed from the GI tract (oral ]). Absorption may be slowed but not decreased when taken with food. Average peak concentration after administration of oral suspension is approximately 25–50% greater than the peak concentration following oral tablet or capsules administration.<ref name="Suprax FDA label" />

''Distribution''
It has high concentrations in ] and ]. It can cross the placenta and its protein binding capacity is 65%.{{medical citation needed|date=July 2015}}

==Contraindications==

Cefixime is contraindicated in patients with known sensitivity or allergies to ] class of ].<ref name="Suprax FDA label">{{cite web | title=Suprax- cefixime tablet Suprax- cefixime capsule Suprax- cefixime tablet, chewable Suprax- cefixime powder, for suspension | website=DailyMed | date=26 November 2019 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d0fd45bd-7d52-4fa6-a5f7-f46d5651ffa2 | access-date=23 April 2020}}</ref><ref>{{cite web | title=Suprax- cefixime powder, for suspension | website=DailyMed | date=2 January 2020 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7e2462b2-bfed-4da4-8c47-46838d6153f8 | access-date=23 April 2020}}</ref> As Cefixime is a third generation cephalosporin, it is not contraindicated for patients with a true penicillin allergy.

==Adverse effects==
{{unreferenced section|date=December 2019}}
Adverse drug reactions include ], ], ] and vomiting.<ref name="AHFS2016" /> Hypersensitivity reactions like skin rashes, ] and ] have been reported.{{medcn|date=August 2023}} There is no specific ] for cefixime overdosage.{{medcn|date=August 2023}}

==Drug interactions==
* Alcohol – No major interaction has been observed between cefixime and alcohol.<ref>{{cite web|url=http://www.nhs.uk/conditions/gonorrhoea/pages/MedicineOverview.aspx?condition=Bacterial%20infections&medicine=Cefixime&preparationCefixime%20100mg/5ml%20oral%20suspension|title=Medicines information links|work = NHS Choices | publisher = UK National Health Service |access-date=22 August 2016|url-status=live|archive-url= https://web.archive.org/web/20150711002908/http://www.nhs.uk/conditions/gonorrhoea/pages/MedicineOverview.aspx?condition=Bacterial%20infections&medicine=Cefixime&preparationCefixime%20100mg%2F5ml%20oral%20suspension |archive-date=11 July 2015}}</ref>{{better source needed|date=July 2015}}

==History==

It was sold under the trade name Suprax 125 in the United States until 2003, when it was taken off the market by drug manufacturer ] after its ] expired.{{citation needed|date=December 2019}} Lupin started selling Suprax in the United States in 2007,<ref name="ANDA 065355">{{cite web | title=Suprax: FDA-Approved Drugs | website=U.S. ] (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=065355 | access-date=23 April 2020}}</ref> and it is available in different formulations and strengths.<ref name="ANDA 065355" /><ref>{{cite web | title=Suprax: FDA-Approved Drugs | website=U.S. ] (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=065380 | access-date=23 April 2020}}</ref><ref>{{cite web | title=Suprax: FDA-Approved Drugs | website=U.S. ] (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=202091 | access-date=23 April 2020}}</ref><ref>{{cite web | title=Suprax: FDA-Approved Drugs | website=U.S. ] (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=203195 | access-date=23 April 2020}}</ref>

==Marketing==
Cefixime is marketed under many ]s worldwide; examples include Fixacef, Pancef, Caricef, Taxim o, Texit, Ofex, Ceftid, Cef-3, Denvar, 3-C, Cefim, Magnett, Oroken, Ofiken, Fix-A, and Zifi.<ref name=genericnames>{{cite web|title=Cefixime—Drugs.com|url=https://www.drugs.com/international/cefixime.html|website=www.drugs.com|access-date=10 December 2016|url-status=live|archive-url=https://web.archive.org/web/20160530044200/http://www.drugs.com/international/cefixime.html|archive-date=30 May 2016}}</ref><ref name="FDC—Products—Formulations">{{cite web |title=FDC—Products—Formulations |website=fdcindia.com |url=http://www.fdcindia.com/formulations.php |access-date=2 May 2018}}</ref> In India it is marketed as Zifi 200 and is commonly ].<ref>{{cite news | vauthors = Perur S |title=Fake drugs: the global industry putting your life at risk |url=https://mosaicscience.com/story/fake-drugs-global-antibiotics-amr-counterfeit-meds/ |access-date=13 December 2018 |publisher=Mosaic |date=30 October 2018}}</ref>

== References ==
{{Reflist}}

{{Cell wall disruptive antibiotics}}
{{Portal bar|Medicine}}


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