| 词条 | Cefixime |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 460023156 | IUPAC_name = (6R,7R)-7[2-(2-Amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | image = Cefixime.svg | tradename = many[1] | Drugs.com = {{drugs.com|monograph|cefixime}} | MedlinePlus = a690007 | pregnancy_category = B | legal_status = Rx-only | routes_of_administration = by mouth (capsule or suspension) | bioavailability = 30 to 50%[2] | protein_bound = Approximately 60% | metabolism = | elimination_half-life = Variable Average 3 to 4 hours | excretion = Kidney and biliary | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 79350-37-1 | ATC_prefix = J01 | ATC_suffix = DD08 | ATC_supplemental = | PubChem = 5362065 | 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 | C=16 | H=15 | N=5 | O=7 | S=2 | molecular_weight = 453.452 g/mol | 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 | 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = OKBVVJOGVLARMR-QSWIMTSFSA-N }}Cefixime is an antibiotic useful to treat a number of bacterial infections.[2] This includes otitis media, strep throat, pneumonia, urinary tract infections, gonorrhea, and Lyme disease.[2] For gonorrhea typically only one dose is required.[1] In the United States it is a second line treatment to ceftriaxone for gonorrhea.[2] It is taken by mouth.[2] Common side effects include diarrhea, abdominal pain, and nausea.[2] Serious side effects may include allergic reactions and Clostridium difficile diarrhea.[2] It is not recommended in people with a history of a severe penicillin allergy.[1] It appears to be relatively safe during pregnancy.[2] It is in the third generation cephalosporin class of medications.[2] It works by disrupting the bacteria's cell wall resulting in its death.[3] Cefixime was patented in 1979 and approved for medical use in the United States in 1989.[3][4] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[5] It is not available as a generic medication in the United States.[17] The wholesale cost in the developing world is about US$0.26–2.09 per dose.[6] In the United States a course of treatment costs about $100–200 as of 2015.[7] Medical usesCefixime treats infections of the: Ear: Otitis caused by Haemophilus influenzae, Moraxella catarrhalis and Streptococcus pyogenes. Sinuses: Sinusitis. Throat: Tonsillitis, pharyngitis caused by Streptococcus pyogenes. Chest and lungs: Bronchitis, pneumonia caused by Streptococcus pneumoniae and Haemophilus influenzae. It is also used to treat typhoid fever.[8] Spectrum of bacterial susceptibilityCefixime 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:[9]
Mechanism of actionThe bactericidal action of Cefixime is due to the inhibition of cell wall synthesis. 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. AbsorptionOnly 40–50% is absorbed from the GI tract (oral bioavailability). Absorption may be 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.[10] DistributionIt 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}} It is always better to perform appropriate cultures and susceptibility studies to determine the causative organism and its sensitivity to cefixime. ContraindicationsCefixime is contraindicated in patients with known sensitivity or allergies to cephalosporin class of antibiotics. As Cefixime is a third generation cephalosporin, it is not contraindicated for patients with a true penicillin allergy.[11] Adverse effectsAdverse drug reactions include diarrhea, dyspepsia, nausea and vomiting. Hypersensitivity reactions like skin rashes, urticaria and Stevens-Johnson syndrome have been reported. Though thrombocytopenia has been reported for many cephalosporins, it has not been reported for cefixime. There is no specific antidote for Cefixime overdosage. Gastric lavage may be performed. Dialysis will not remove Cefixime in significant quantities. Drug interactions
HistoryIt was sold under the trade name Suprax 125 in the USA until 2003 when it was taken off the market by drug manufacturer Wyeth after its patent expired. MarketingCefixime is marketed under many trade names worldwide; examples include Taxim o, Texit, Cef-3, Denvar, 3-C, Cefim, Magnett, Oroken, Ofiken, Fix-A, and Zifi.[13][14] In India it is marketed as Zifi 200 and is commonly counterfeited.[15] References1. ^1 {{cite book|title=WHO Model Formulary 2008|date=2009|publisher=World Health Organization|isbn=9789241547659|page=107|url=http://apps.who.int/medicinedocs/documents/s16879e/s16879e.pdf|accessdate=8 December 2016|deadurl=no|archiveurl=https://web.archive.org/web/20161213060118/http://apps.who.int/medicinedocs/documents/s16879e/s16879e.pdf|archivedate=13 December 2016|df=}} {{CephalosporinAntiBiotics}}{{portal bar|Pharmacy and pharmacology|Medicine}}2. ^{{cite web|title=Cefixime (Suprax) Use During Pregnancy|url=https://www.drugs.com/pregnancy/cefixime.html|website=www.drugs.com|deadurl=no|archiveurl=https://web.archive.org/web/20161220224931/https://www.drugs.com/pregnancy/cefixime.html|archivedate=2016-12-20|df=}} 3. ^1 2 3 4 5 6 7 8 9 {{cite web|title=Cefixime|url=https://www.drugs.com/monograph/cefixime.html|publisher=The American Society of Health—System Pharmacists|accessdate=8 December 2016|deadurl=no|archiveurl=https://web.archive.org/web/20161127220806/https://www.drugs.com/monograph/cefixime.html|archivedate=27 November 2016|df=}} 4. ^{{cite book |last1=Fischer |first1=Jnos |last2=Ganellin |first2=C. Robin |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=495 |url=https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA495 |language=en}} 5. ^{{cite web|title=WHO Model List of Essential Medicines (19th List)|url=http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|work=World Health Organization|accessdate=8 December 2016|date=April 2015|deadurl=no|archiveurl=https://web.archive.org/web/20161213052708/http://www.who.int/medicines/publications/essentialmedicines/EML_2015_FINAL_amended_NOV2015.pdf?ua=1|archivedate=13 December 2016|df=}} 6. ^{{cite web|title=Cefixime |url=http://mshpriceguide.org/en/single-drug-information/?DMFId=1131&searchYear=2014|website=International Drug Price Indicator Guide|accessdate=8 December 2016}} 7. ^1 {{cite book|last1=Hamilton|first1=Richart|title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=9781284057560|page=86}} 8. ^{{cite web|title=Mechanism of Therapeutic Effectiveness of Cefixime against Typhoid Fever|url=http://aac.asm.org/content/45/9/2450.full#ref-3|work=Antimicrobial Agents and Chemotherapy|accessdate=7 April 2016|date=September 2001|deadurl=no|archiveurl=https://web.archive.org/web/20151202010015/http://aac.asm.org/content/45/9/2450.full#ref-3|archivedate=2 December 2015|df=}} 9. ^http://www.toku-e.com/Assets/MIC/Cefixime%20trihydrate.pdf 10. ^{{cite web|title=SUPRAX Package Insert|url=http://www.supraxrx.com/pdf/Suprax-Final%20PI%20-PDF%20File.pdf|work=Lupin Pharmaceuticals, Inc.|accessdate=7 April 2016|date=March 2013|deadurl=no|archiveurl=https://web.archive.org/web/20150223221244/http://supraxrx.com/pdf/Suprax-Final%20PI%20-PDF%20File.pdf|archivedate=23 February 2015|df=}} 11. ^http://www.cks.nhs.uk/gonorrhoea/prescribing_information/prescribing_information/cephalosporins_ceftriaxone_or_cefixime{{dead link|date=August 2017 |bot=InternetArchiveBot |fix-attempted=yes }} 12. ^{{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|publisher=NHS Choices|first=N. H. S.|last=Choices|work=www.nhs.uk|accessdate=22 August 2016|deadurl=no|archiveurl=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|archivedate=11 July 2015|df=}} 13. ^1 {{cite web|title=Cefixime - Drugs.com|url=https://www.drugs.com/international/cefixime.html|website=www.drugs.com|accessdate=10 December 2016|deadurl=no|archiveurl=https://web.archive.org/web/20160530044200/http://www.drugs.com/international/cefixime.html|archivedate=30 May 2016|df=}} 14. ^{{cite web |title=FDC - Products - Formulations |website=fdcindia.com |url=http://www.fdcindia.com/formulations.php |access-date=2018-05-02}} 15. ^{{cite news |title=Fake drugs: the global industry putting your life at risk |url=https://mosaicscience.com/story/fake-drugs-global-antibiotics-amr-counterfeit-meds/ |accessdate=13 December 2018 |publisher=Mosaic |date=30 October 2018}} 4 : Cephalosporin antibiotics|Thiazoles|World Health Organization essential medicines|RTT |
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