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Cefixime

Cefixime, sold under the brand name Suprax among others, is an antibiotic medication used to treat a number of bacterial infections.[3] These infections include otitis media, strep throat, pneumonia, urinary tract infections, gonorrhea, and Lyme disease.[3] For gonorrhea typically only one dose is required.[4] In the United States it is a second-line treatment to ceftriaxone for gonorrhea.[3] It is taken by mouth.[3]

Cefixime
Clinical data
Trade namesSuprax, others[1]
AHFS/Drugs.comMonograph
MedlinePlusa690007
License data
Routes of
administration
By mouth
ATC code
Legal status
Legal status
  • UK: POM (Prescription only)[2]
  • US: ℞-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability30 to 50%[3]
Protein bindingApproximately 60%
Elimination half-lifeVariable
Average 3 to 4 hours
ExcretionKidney and biliary
Identifiers
  • (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
CAS Number
  • 79350-37-1 Y
PubChem CID
  • 5362065
DrugBank
  • DB00671 Y
ChemSpider
  • 4514923 Y
UNII
  • XZ7BG04GJX
KEGG
  • D00258 Y
ChEBI
  • CHEBI:472657 Y
ChEMBL
  • ChEMBL1541 Y
CompTox Dashboard (EPA)
  • DTXSID7022754
ECHA InfoCard100.119.331
Chemical and physical data
FormulaC16H15N5O7S2
Molar mass453.44 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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
  • InChI=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 Y
  • Key:OKBVVJOGVLARMR-QSWIMTSFSA-N Y
 NY (what is this?)  (verify)

Common side effects include diarrhea, abdominal pain, and nausea.[3] Serious side effects may include allergic reactions and Clostridium difficile diarrhea.[3] It is not recommended in people with a history of a severe penicillin allergy.[4] It appears to be relatively safe during pregnancy.[5] It is in the third-generation cephalosporin class of medications.[3] 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][6] It is on the World Health Organization's List of Essential Medicines.[7] It is available as a generic medication in the United States.[8]

Medical uses edit

Cefixime treats infections of the:

It is also used to treat typhoid fever.[11][12][3]

Spectrum of bacterial susceptibility edit

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:[13]

  • Escherichia coli: 0.015 µg/mL – 4 µg/mL
  • Haemophilus influenzae: ≤0.004 µg/mL – >4 µg/mL
  • Proteus mirabilis: ≤0.008 µg/mL – 0.06 µg/mL
  • Streptococcus pneumoniae: 0.12 µg/mL[10]
  • Staphylococcus aureus: >128 µg/mL (Resistant)[10]
  • Enterobacter spp.: >128 µg/mL (Resistant) [10]

Mechanism of action edit

The bactericidal action of Cefixime is due to the inhibition of cell wall synthesis.[medical citation needed] 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.[medical citation needed]

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.[9]

Distribution It has high concentrations in bile and urine. It can cross the placenta and its protein binding capacity is 65%.[medical citation needed]

Contraindications edit

Cefixime is contraindicated in patients with known sensitivity or allergies to cephalosporin class of antibiotics.[9][14] As Cefixime is a third generation cephalosporin, it is not contraindicated for patients with a true penicillin allergy.

Adverse effects edit

Adverse drug reactions include diarrhea, dyspepsia, nausea and vomiting.[3] Hypersensitivity reactions like skin rashes, urticaria and Stevens–Johnson syndrome have been reported.[medical citation needed] There is no specific antidote for cefixime overdosage.[medical citation needed]

Drug interactions edit

History edit

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] Lupin started selling Suprax in the United States in 2007,[16] and it is available in different formulations and strengths.[16][17][18][19]

Marketing edit

Cefixime is marketed under many brand names worldwide; examples include Pancef, Caricef, Taxim o, Texit, Ofex, Ceftid, Cef-3, Denvar, 3-C, Cefim, Magnett, Oroken, Ofiken, Fix-A, and Zifi.[1][20] In India it is marketed as Zifi 200 and is commonly counterfeited.[21]

References edit

  1. ^ a b "Cefixime—Drugs.com". www.drugs.com. from the original on 30 May 2016. Retrieved 10 December 2016.
  2. ^ a b c d e f . (emc). 20 August 2019. Archived from the original on 22 September 2020. Retrieved 23 April 2020.
  3. ^ a b c d e f g h i j k l m n o p q "Cefixime". The American Society of Health—System Pharmacists. from the original on 27 November 2016. Retrieved 8 December 2016.
  4. ^ a b World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. p. 107. hdl:10665/44053. ISBN 9789241547659.
  5. ^ "Cefixime (Suprax) Use During Pregnancy". Drugs.com. 29 March 2019. Retrieved 24 December 2019.
  6. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 495. ISBN 9783527607495.
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  8. ^ "Generic Suprax Availability". Drugs.com. Retrieved 23 April 2020.
  9. ^ a b c d e f g "Suprax- cefixime tablet Suprax- cefixime capsule Suprax- cefixime tablet, chewable Suprax- cefixime powder, for suspension". DailyMed. 26 November 2019. Retrieved 23 April 2020.
  10. ^ a b c d Grayson ML (2017). Kucers' the use of antibiotics : a clinical review of antibacterial, antifungal, antiparasitic and antiviral drugs (Seventh ed.). Boca Raton. ISBN 978-1-315-15211-0. OCLC 1011357224.{{cite book}}: CS1 maint: location missing publisher (link)
  11. ^ Matsumoto Y, Ikemoto A, Wakai Y, Ikeda F, Tawara S, Matsumoto K (September 2001). "Mechanism of therapeutic effectiveness of cefixime against typhoid fever". Antimicrobial Agents and Chemotherapy. 45 (9): 2450–2454. doi:10.1128/aac.45.9.2450-2454.2001. PMC 90676. PMID 11502513.
  12. ^ Bhutta ZA, Khan IA, Molla AM (November 1994). "Therapy of multidrug-resistant typhoid fever with oral cefixime vs. intravenous ceftriaxone". The Pediatric Infectious Disease Journal. 13 (11): 990–994. doi:10.1097/00006454-199411000-00010. PMID 7845753.
  13. ^ "Cefixime trihydrate Susceptibility and Minimum Inhibitory Concentration (MIC) Data" (PDF). www.toku-e.com.
  14. ^ "Suprax- cefixime powder, for suspension". DailyMed. 2 January 2020. Retrieved 23 April 2020.
  15. ^ "Medicines information links". NHS Choices. UK National Health Service. from the original on 11 July 2015. Retrieved 22 August 2016.
  16. ^ a b "Suprax: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 23 April 2020.
  17. ^ "Suprax: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 23 April 2020.
  18. ^ "Suprax: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 23 April 2020.
  19. ^ "Suprax: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 23 April 2020.
  20. ^ "FDC—Products—Formulations". fdcindia.com. Retrieved 2 May 2018.
  21. ^ Perur S (30 October 2018). "Fake drugs: the global industry putting your life at risk". Mosaic. Retrieved 13 December 2018.

cefixime, sold, under, brand, name, suprax, among, others, antibiotic, medication, used, treat, number, bacterial, infections, these, infections, include, otitis, media, strep, throat, pneumonia, urinary, tract, infections, gonorrhea, lyme, disease, gonorrhea,. Cefixime sold under the brand name Suprax among others is an antibiotic medication used to treat a number of bacterial infections 3 These infections include otitis media strep throat pneumonia urinary tract infections gonorrhea and Lyme disease 3 For gonorrhea typically only one dose is required 4 In the United States it is a second line treatment to ceftriaxone for gonorrhea 3 It is taken by mouth 3 CefiximeClinical dataTrade namesSuprax others 1 AHFS Drugs comMonographMedlinePlusa690007License dataUS DailyMed CefiximeRoutes ofadministrationBy mouthATC codeJ01DD08 WHO Legal statusLegal statusUK POM Prescription only 2 US only In general Prescription only Pharmacokinetic dataBioavailability30 to 50 3 Protein bindingApproximately 60 Elimination half lifeVariableAverage 3 to 4 hoursExcretionKidney and biliaryIdentifiersIUPAC 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 acidCAS Number79350 37 1 YPubChem CID5362065DrugBankDB00671 YChemSpider4514923 YUNIIXZ7BG04GJXKEGGD00258 YChEBICHEBI 472657 YChEMBLChEMBL1541 YCompTox Dashboard EPA DTXSID7022754ECHA InfoCard100 119 331Chemical and physical dataFormulaC 16H 15N 5O 7S 2Molar mass453 44 g mol 13D model JSmol Interactive imageSMILES O C2N1 C C C C CS C H 1 C H 2NC O C N OCC O O c3nc sc3 N C O OInChI InChI 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 YKey OKBVVJOGVLARMR QSWIMTSFSA N Y N Y what is this verify Common side effects include diarrhea abdominal pain and nausea 3 Serious side effects may include allergic reactions and Clostridium difficile diarrhea 3 It is not recommended in people with a history of a severe penicillin allergy 4 It appears to be relatively safe during pregnancy 5 It is in the third generation cephalosporin class of medications 3 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 6 It is on the World Health Organization s List of Essential Medicines 7 It is available as a generic medication in the United States 8 Contents 1 Medical uses 1 1 Spectrum of bacterial susceptibility 2 Mechanism of action 3 Contraindications 4 Adverse effects 5 Drug interactions 6 History 7 Marketing 8 ReferencesMedical uses editCefixime treats infections of the Urinary tract Uncomplicated urinary tract infections caused by susceptible isolates of Escherichia coli and Proteus mirabilis 9 2 3 Ear Otitis media caused by Haemophilus influenzae Moraxella catarrhalis and Streptococcus pyogenes 9 2 3 Throat Tonsillitis and pharyngitis caused by Streptococcus pyogenes 9 2 3 Chest and lungs Chronic bronchitis caused by Streptococcus pneumoniaeand Haemophilus influenzae 9 2 3 Cervix and urethra Gonorrhea cervical urethral caused by susceptible isolates of Neisseria gonorrhoeae penicillinase and non penicillinase producing isolates 9 2 3 Skin and soft tissue infection effective against group A and B beta hemolytic streptococci However Staphylococcus aureus coagulase negative staphylococci and enterococci are resistant 10 It is also used to treat typhoid fever 11 12 3 Spectrum of bacterial susceptibility edit 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 13 Escherichia coli 0 015 µg mL 4 µg mL Haemophilus influenzae 0 004 µg mL gt 4 µg mL Proteus mirabilis 0 008 µg mL 0 06 µg mL Streptococcus pneumoniae 0 12 µg mL 10 Staphylococcus aureus gt 128 µg mL Resistant 10 Enterobacter spp gt 128 µg mL Resistant 10 Mechanism of action editThe bactericidal action of Cefixime is due to the inhibition of cell wall synthesis medical citation needed 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 medical citation needed 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 9 Distribution It has high concentrations in bile and urine It can cross the placenta and its protein binding capacity is 65 medical citation needed Contraindications editCefixime is contraindicated in patients with known sensitivity or allergies to cephalosporin class of antibiotics 9 14 As Cefixime is a third generation cephalosporin it is not contraindicated for patients with a true penicillin allergy Adverse effects editThis section does not cite any sources Please help improve this section by adding citations to reliable sources Unsourced material may be challenged and removed December 2019 Learn how and when to remove this template message Adverse drug reactions include diarrhea dyspepsia nausea and vomiting 3 Hypersensitivity reactions like skin rashes urticaria and Stevens Johnson syndrome have been reported medical citation needed There is no specific antidote for cefixime overdosage medical citation needed Drug interactions editAlcohol No major interaction has been observed between cefixime and alcohol 15 better source needed History editIt 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 Lupin started selling Suprax in the United States in 2007 16 and it is available in different formulations and strengths 16 17 18 19 Marketing editCefixime is marketed under many brand names worldwide examples include Pancef Caricef Taxim o Texit Ofex Ceftid Cef 3 Denvar 3 C Cefim Magnett Oroken Ofiken Fix A and Zifi 1 20 In India it is marketed as Zifi 200 and is commonly counterfeited 21 References edit a b Cefixime Drugs com www drugs com Archived from the original on 30 May 2016 Retrieved 10 December 2016 a b c d e f Suprax 200 mg Tablets Summary of Product Characteristics SmPC emc 20 August 2019 Archived from the original on 22 September 2020 Retrieved 23 April 2020 a b c d e f g h i j k l m n o p q Cefixime The American Society of Health System Pharmacists Archived from the original on 27 November 2016 Retrieved 8 December 2016 a b World Health Organization 2009 Stuart MC Kouimtzi M Hill SR eds WHO Model Formulary 2008 p 107 hdl 10665 44053 ISBN 9789241547659 Cefixime Suprax Use During Pregnancy Drugs com 29 March 2019 Retrieved 24 December 2019 Fischer J Ganellin CR 2006 Analogue based Drug Discovery John Wiley amp Sons p 495 ISBN 9783527607495 World Health Organization 2019 World Health Organization model list of essential medicines 21st list 2019 Geneva World Health Organization hdl 10665 325771 WHO MVP EMP IAU 2019 06 License CC BY NC SA 3 0 IGO Generic Suprax Availability Drugs com Retrieved 23 April 2020 a b c d e f g Suprax cefixime tablet Suprax cefixime capsule Suprax cefixime tablet chewable Suprax cefixime powder for suspension DailyMed 26 November 2019 Retrieved 23 April 2020 a b c d Grayson ML 2017 Kucers the use of antibiotics a clinical review of antibacterial antifungal antiparasitic and antiviral drugs Seventh ed Boca Raton ISBN 978 1 315 15211 0 OCLC 1011357224 a href Template Cite book html title Template Cite book cite book a CS1 maint location missing publisher link Matsumoto Y Ikemoto A Wakai Y Ikeda F Tawara S Matsumoto K September 2001 Mechanism of therapeutic effectiveness of cefixime against typhoid fever Antimicrobial Agents and Chemotherapy 45 9 2450 2454 doi 10 1128 aac 45 9 2450 2454 2001 PMC 90676 PMID 11502513 Bhutta ZA Khan IA Molla AM November 1994 Therapy of multidrug resistant typhoid fever with oral cefixime vs intravenous ceftriaxone The Pediatric Infectious Disease Journal 13 11 990 994 doi 10 1097 00006454 199411000 00010 PMID 7845753 Cefixime trihydrate Susceptibility and Minimum Inhibitory Concentration MIC Data PDF www toku e com Suprax cefixime powder for suspension DailyMed 2 January 2020 Retrieved 23 April 2020 Medicines information links NHS Choices UK National Health Service Archived from the original on 11 July 2015 Retrieved 22 August 2016 a b Suprax FDA Approved Drugs U S Food and Drug Administration FDA Retrieved 23 April 2020 Suprax FDA Approved Drugs U S Food and Drug Administration FDA Retrieved 23 April 2020 Suprax FDA Approved Drugs U S Food and Drug Administration FDA Retrieved 23 April 2020 Suprax FDA Approved Drugs U S Food and Drug Administration FDA Retrieved 23 April 2020 FDC Products Formulations fdcindia com Retrieved 2 May 2018 Perur S 30 October 2018 Fake drugs the global industry putting your life at risk Mosaic Retrieved 13 December 2018 Portal nbsp Medicine Retrieved from https en wikipedia org w index php title Cefixime amp oldid 1186204959, wikipedia, wiki, book, books, library,

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