cefixime
{{Short description|A third generation cephalosporin antibiotic}}
{{Use dmy dates|date=April 2024}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 460023156
| image = Cefixime skeletal structure.svg
| image_class = skin-invert-image
| width =
| alt =
| caption =
| image2 = Cefixime ball-and-stick model from xtal 2013.png
| pronounce =
| Drugs.com = {{drugs.com|monograph|cefixime}}
| MedlinePlus = a690007
| DailyMedID = Cefixime
| pregnancy_AU =
| pregnancy_AU_comment =
| pregnancy_category =
| routes_of_administration = By mouth
| class =
| ATC_prefix = J01
| ATC_suffix = DD08
| ATC_supplemental =
| legal_AU =
| legal_AU_comment =
| legal_BR =
| legal_BR_comment =
| legal_CA = Rx-only
| legal_CA_comment = {{cite web | title=Antibiotics | website=Health Canada | 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}}{{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}}
| legal_DE =
| legal_DE_comment =
| legal_NZ =
| legal_NZ_comment =
| legal_UK = POM
| legal_US = Rx-only
| legal_US_comment =
| legal_UN =
| legal_UN_comment =
| legal_status = Rx-only
| protein_bound = Approximately 60%
| metabolism =
| metabolites =
| onset =
| elimination_half-life = Variable
Average 3 to 4 hours
| duration_of_action =
| excretion = Kidney and biliary
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 79350-37-1
| CAS_supplemental =
| PubChem = 5362065
| IUPHAR_ligand =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00671
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4514923
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = XZ7BG04GJX
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00258
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 472657
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1541
| NIAID_ChemDB =
| PDB_ligand =
| synonyms =
| IUPAC_name = (6R,7R)-7-{[2-(2-Amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino}-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
| C=16 | H=15 | N=5 | O=7 | S=2
| SMILES = O=C2N1/C(=C(/C=C)CS[C@@H]1[C@@H]2NC(=O)C(=N\OCC(=O)O)/c3nc(sc3)N)C(=O)O
| Jmol =
| 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_comment =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OKBVVJOGVLARMR-QSWIMTSFSA-N
| density =
| density_notes =
| melting_point =
| melting_high =
| melting_notes =
| boiling_point =
| boiling_notes =
| solubility =
| sol_units =
| specific_rotation =
}}
Cefixime, sold under the brand name Suprax among others, is an antibiotic medication used to treat a number of bacterial infections. These infections include otitis media, strep throat, pneumonia, urinary tract infections, gonorrhea, and Lyme disease. For gonorrhea typically only one dose is required.{{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 }} In the United States it is a second-line treatment to ceftriaxone for gonorrhea. It is taken by mouth.
Common side effects include diarrhea, abdominal pain, and nausea. Serious side effects may include allergic reactions and Clostridioides difficile diarrhea. It is not recommended in people with a history of a severe penicillin allergy. It appears to be relatively safe during 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}} It is in the third-generation cephalosporin class of medications. It works by disrupting the bacteria's cell wall resulting in its death.{{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}}
Cefixime was patented in 1979 and approved for medical use in the United States in 1989.{{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 }} It is on the World Health Organization's List of Essential Medicines.{{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 }} It is available as a generic medication in the United States.{{cite web | title=Generic Suprax Availability | website=Drugs.com | url=https://www.drugs.com/availability/generic-suprax.html | access-date=23 April 2020}}
Medical uses
Cefixime treats infections of the:
- Urinary tract: Uncomplicated urinary tract infections caused by susceptible isolates of Escherichia coli and Proteus mirabilis.
- Ear: Otitis media caused by Haemophilus influenzae, Moraxella catarrhalis and Streptococcus pyogenes.
- Throat: Tonsillitis and pharyngitis caused by Streptococcus pyogenes.
- Chest and lungs: Chronic bronchitis caused by Streptococcus pneumoniae and Haemophilus influenzae.
- Cervix and urethra: Gonorrhea (cervical/urethral) caused by susceptible isolates of Neisseria gonorrhoeae (penicillinase-and non-penicillinase-producing isolates).
- Skin and soft tissue infection: effective against group A and B beta-hemolytic streptococci. However, Staphylococcus aureus, coagulase-negative staphylococci and enterococci are resistant.{{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}}
It is also used to treat typhoid fever.{{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 }}{{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 }}
=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:{{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 }}
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 penicillin binding proteins (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 bioavailability). 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.
Distribution
It has high concentrations in bile and urine. 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 cephalosporin class of antibiotics.{{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}}{{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}} 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 diarrhea, dyspepsia, nausea and vomiting. Hypersensitivity reactions like skin rashes, urticaria and Stevens–Johnson syndrome have been reported.{{medcn|date=August 2023}} There is no specific antidote for cefixime overdosage.{{medcn|date=August 2023}}
Drug interactions
- Alcohol – No major interaction has been observed between cefixime and alcohol.{{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}}{{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 Wyeth after its patent expired.{{citation needed|date=December 2019}} Lupin started selling Suprax in the United States in 2007,{{cite web | title=Suprax: FDA-Approved Drugs | website=U.S. Food and Drug Administration (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=065355 | access-date=23 April 2020}} and it is available in different formulations and strengths.{{cite web | title=Suprax: FDA-Approved Drugs | website=U.S. Food and Drug Administration (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=065380 | access-date=23 April 2020}}{{cite web | title=Suprax: FDA-Approved Drugs | website=U.S. Food and Drug Administration (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=202091 | archive-url=https://web.archive.org/web/20170317144801/http://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=202091 | url-status=dead | archive-date=17 March 2017 | access-date=23 April 2020}}{{cite web | title=Suprax: FDA-Approved Drugs | website=U.S. Food and Drug Administration (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=203195 | access-date=23 April 2020}}
Marketing
Cefixime is marketed under many brand names worldwide; examples include Fixacef, Pancef, Caricef, Taxim o, Texit, Ofex, Ceftid, Cef-3, Denvar, 3-C, Cefim, Magnett, Oroken, Ofiken, Fix-A, and Zifi.{{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}}{{cite web |title=FDC—Products—Formulations |website=fdcindia.com |url=http://www.fdcindia.com/formulations.php |access-date=2 May 2018}} In India it is marketed as Zifi 200 and is commonly counterfeited.{{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 |archive-date=11 April 2020 |archive-url=https://web.archive.org/web/20200411072051/https://mosaicscience.com/story/fake-drugs-global-antibiotics-amr-counterfeit-meds/ |url-status=dead }}
References
{{Reflist}}
{{Cell wall disruptive antibiotics}}
{{Portal bar|Medicine}}
Category:Cephalosporin antibiotics
Category:World Health Organization essential medicines