Cefixime
Identification
- Summary
Cefixime is a third generation cephalosporin used to treat susceptible Gram-negative and Gram-positive bacterial infections.
- Brand Names
- Suprax
- Generic Name
- Cefixime
- DrugBank Accession Number
- DB00671
- Background
Bacteria possess a cell wall comprising a glycopeptide polymer commonly known as peptidoglycan, which is synthesized and remodelled through the action of a family of enzymes known as "penicillin-binding proteins" (PBPs).8 β-lactam antibiotics, including cephalosporins, are PBP inhibitors that, through inhibition of essential PBPs, result in impaired cell wall homeostasis, loss of cell integrity, and ultimately bacterial cell death.8,9,10 Cefixime is a broad-spectrum antibiotic and an orally-active third-generation semisynthetic cephalosporin.3,15,21 Cephalosporins are beta-lactam antibiotics and can be used to treat gram-positive and gram-negative bacterial infections which include conditions such as skin infections, resistant bacteria, and meningitis.12 Examples of third-generation cephalosporins are ceftriaxone, cefotaxime, and ceftazidime.12
Third-generation cephalosporins are often a first-line therapy against certain bacterial infections.17 However, cefixime is not recommended as a first-line of treatment for uncomplicated urogenital, anorectal, or pharyngeal gonorrhea because cefixime does not provide the same bactericidal effect as ceftriaxone.24,16 Generally, cefixime is used to treat uurinary tract infections, middle ear infections, pharyngitis, tonsillitis, exacerbations of chronic bronchitis, and uncomplicated gonorrhea.21 The beta-lactam ring of cefixime inhibits bacterial cell wall synthesis by binding to the penicillin-binding proteins which will then result in lysis.12,7,6 Specifically, cephalosporins inhibit penicillin-sensitive enzymes responsible for the final 3D structure of the bacterial cell wall which in turn inhibit bacterial cell wall peptidoglycan synthesis.19,20 Additionally, third-generation cephalosporins have been shown to have more stability in the presence of beta-lactamases compared to first- and second-generation cephalosporins.18 Cefixime was first approved in the United States in 1986.21
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
- Weight
- Average: 453.45
Monoisotopic: 453.041289239 - Chemical Formula
- C16H15N5O7S2
- Synonyms
- (−)-cefixim
- Cefixim
- Cefixima
- Céfixime
- Cefixime
- Cefixime anhydrous
- Cefiximum
- External IDs
- CL284635
- FK 027
- FK027
- FR 17027
- FR17027
Pharmacology
- Indication
Cefixime is indicated for the treatment of uncomplicated urinary tract infections caused by Escherichia coli and Proteus mirabilis, otitis media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pyogenes, pharyngitis and tonsillitis caused by Streptococcus pyogenes, acute exacerbations of chronic bronchitis caused by Streptococcus pneumoniae and Haemophilus influenzae, and uncomplicated gonorrhea (cervical/urethral) caused by Neisseria gonorrhoeae (penicillinase-and non-penicillinase-producing isolates).21
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Acute exacerbation of chronic bronchitis caused by streptococcus pneumoniae •••••••••••• •••••••• ••••••••••• ••••••• ••••••• •••••••• Treatment of Acute exacerbations of chronic bronchitis caused by haemophilus influenzae •••••••••••• •••••••• ••••••••••• ••••••• ••••••• •••••••• Treatment of Community acquired pneumonia ••• ••••• Treatment of Gonorrhea of anus ••• ••••• Treatment of Lyme disease ••• ••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Cefixime, a broad-spectrum antibiotic, is an orally-active third-generation semisynthetic cephalosporin.3,21 Like other cephalosporins, the antibacterial action of cefixime results from inhibition of cell wall synthesis.21 Also like other cephalosporins, cefixime is stable when in the presence of certain beta-lactamase enzymes, which means certain organisms resistant to penicillins and some cephalosporins due to the presence of beta-lactamases could be susceptible to cefixime.21
Use of cefixime can result in hypersensitivity reactions including anaphylactic/anaphylactoid reactions and Clostridium difficile-associated diarrhea (CDAD); it may also be associated with a fall in prothrombin activity.21 Cefixime doses should be adjusted for patients that have renal impairment and patients undergoing continuous ambulatory peritoneal dialysis (CAPD) and hemodialysis (HD), while patients on dialysis should be monitored while taking cefixime.21
- Mechanism of action
The bacterial cell wall, which is located at the periphery of Gram-positive bacteria and within the periplasm of Gram-negative bacteria, comprises a glycopeptide polymer synthesized through cross-linking of glycans to peptide stems on alternating saccharides, which is known commonly as peptidoglycan.8 Cell wall formation, recycling, and remodelling require numerous enzymes, including a family of enzymes with similar active site character despite distinct and sometimes overlapping roles as carboxypeptidases, endopeptidases, transpeptidases, and transglycosylases, known as "penicillin-binding proteins" (PBPs). The number of PBPs differs between bacteria, in which some are considered essential and others redundant. In general, inhibition of one or more essential PBPs results in impaired cell wall homeostasis, loss of cell integrity, and is ultimately bactericidal.8,9,10
Cefixime is a cephalosporin and cephalosporins work by using their beta-lactam rings to inhibit bacterial cell wall synthesis by binding to the penicillin-binding proteins transpeptidases on bacteria.12,7,6 The inhibition of synthesis of the bacteria cell wall will cause lysis, particularly in fast growing organisms such as bacteria.7 Specifically, cephalosporins inhibit penicillin-sensitive enzymes responsible for the final 3D structure of the bacterial cell wall which in turn inhibit bacterial cell wall peptidoglycan synthesis.19,20
Target Actions Organism APenicillin-binding protein binderGram positive and gram negative bacteria UPenicillin-binding protein 2 Not Available Escherichia coli (strain K12) - Absorption
With oral administration of cefixime, about 40%-50% is absorbed whether administered with or without food.21 However, time to maximal absorption is increased approximately 0.8 hours when administered with food.21
Cefixime administered as an single oral 200 mg tablet in healthy male volunteers had a corresponding Cmax of 3.25 mg/L and a corresponding Tmax of 4 hours.13 Administration of cefixime as a 200 mg oral solution in healthy volunteers results in a Cmax of 3.22 micrograms/mL, while administration of 200 mg and 400 mg cefixime capsules results in a Cmax of 2.92 micrograms/mL and 4.84 micrograms/mL, respectively.14 Administration of cefixime as a 200 mg intravenous solution, a 200 mg oral solution, a 200 mg capsule, and 400 mg capsule results in mean areas under the curve (AUC) of 47.0 μg.h/mL, 26.0 μg.h/mL, 23.6 μg.h/mL, and 39.4 μg.h/mL, respectively.14
- Volume of distribution
Cefixime has a volume of distribution averaging 0.1 L/kg of body weight when administered orally.5
- Protein binding
Approximately 65% of cefixime is bound to serum protein, the serum protein binding is also concentration-independent.21
- Metabolism
There is no evidence of metabolism of cefixime in vivo.21
- Route of elimination
Approximately 50% of absorbed cefixime is excreted unchanged in the urine in 24 hours.21
- Half-life
Cefixime has a serum half-life averaging 3 to 4 hours in healthy subjects and is independent of dosage form.4,21 It has ranged up to 9 hours in some normal volunteers.21 In individuals with severe renal impairment (5 to 20 mL/min creatinine clearance), the half-life of cefixime increased to an average of 11.5 hours.21
- Clearance
Cefixime administered as an oral suspension with a dose of 8 mg/kg in children with urinary tract infections aged from 6 to 13 years resulted in a mean apparent total clearance rate of 4.74 ml/min/kg.11
- Adverse Effects
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- Toxicity
Toxicity information specific to cefixime is not conclusive. Symptoms of overdose can include severe vomiting and seizures.22 As cefixime is a cephalosporin, it may trigger seizures, particularly in patients with renal impairment when the dosage was not reduced.21 Additionally, patients experiencing an overdose are at an increased risk of severe adverse effects such as diarrhea, nausea, loose stools, abdominal pain, dyspepsia, and vomiting.21 In case of overdose, no specific antidote exists and this drug is not removed in significant quantities from the circulation by hemodialysis or peritoneal dialysis; however, gastric lavage may be indicated.21 Symptomatic and supportive measures are recommended.
Animal studies revealed an oral LD50 greater than 10g/kg in rats.23
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Cefixime. Acenocoumarol The risk or severity of bleeding can be increased when Cefixime is combined with Acenocoumarol. Alteplase The therapeutic efficacy of Alteplase can be decreased when used in combination with Cefixime. Ambroxol The risk or severity of methemoglobinemia can be increased when Cefixime is combined with Ambroxol. Ancrod The therapeutic efficacy of Ancrod can be decreased when used in combination with Cefixime. - Food Interactions
- Take with or without food. The capsule and tablet may be administered without regard to food. However, the time to maximal absorption is increased approximately 0.8 hours when administered with food while taking with food reduces the absorption following administration of the capsule by approximately 15% based on AUC and 25% based on Cmax.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Cefixime trihydrate 97I1C92E55 125110-14-7 IPYWNMVPZOAFOQ-NABDTECSSA-N - Product Images
- International/Other Brands
- Cefixoral (Menarini) / Cefspan (GlaxoSmithKline) / Cephoral (Merck) / Fixam (Solas) / Fixspor (Invision) / Hifen (Hetero) / InfectoOpticef (Infectopharm) / Kuracef (Sanofi-Aventis) / Letix (Adley) / Ofex (Delta) / Omnatax-O (Abbott) / Oracef (Micro Labs) / Oroken (Sanofi Aventis) / Sancefix (Sandoz) / Secef (Novartis) / Supran (Teva) / Suprax 125 (Lupin) / Tricef (Merck) / Unixime (Firma) / Uro-Cephoral (Merck)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Suprax Powder, for suspension 100 mg / 5 mL Oral Odan Laboratories Ltd 1990-12-31 Not applicable Canada Suprax Powder, for solution 100 mg / 5 mL Oral Aventis Pharma Ltd. 1990-12-31 2005-12-07 Canada Suprax Capsule 400 mg/1 Oral LUPIN LIMITED 2013-03-15 2018-12-03 US Suprax Capsule 400 mg/1 Oral PD-Rx Pharmaceuticals, Inc. 2013-03-15 Not applicable US Suprax Capsule 400 mg/1 Oral Lupin Pharmaceuticals, Inc. 2013-03-15 2021-05-31 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Auro-cefixime Tablet 400 mg Oral Auro Pharma Inc 2014-10-24 Not applicable Canada Auro-cefixime Powder, for suspension 100 mg / 5 mL Oral Auro Pharma Inc 2018-01-08 Not applicable Canada Cefixime Powder, for suspension 100 mg/5mL Oral Belcher Pharmaceuticals,LLC 2017-03-15 Not applicable US Cefixime Capsule 400 mg/1 Oral Lupin Pharmaceuticals, Inc. 2020-10-14 Not applicable US Cefixime Powder, for suspension 200 mg/5mL Oral Lupin Pharmaceuticals, Inc. 2015-04-24 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image INNOCEF PLUS 100/62.5 MG SASE, 20 ADET Cefixime trihydrate (111.9 mg) + Clavulanate potassium (62.5 mg) Powder Oral VİTALİS İLAÇ SAN. TİC. A.Ş. 2011-11-11 Not applicable Turkey INNOCEF PLUS 200/125 MG SAŞE, 20 ADET Cefixime trihydrate (223.8 mg) + Clavulanate potassium (125 mg) Powder Oral VİTALİS İLAÇ SAN. TİC. A.Ş. 2012-10-19 Not applicable Turkey INNOCEF PLUS 200/62.5 MG SASE, 20 ADET Cefixime trihydrate (223.8 mg) + Clavulanate potassium (62.5 mg) Powder Oral VİTALİS İLAÇ SAN. TİC. A.Ş. 2011-11-04 Not applicable Turkey INNOCEF PLUS 400/125 MG SAŞE, 10 ADET Cefixime trihydrate (447.63 mg) + Clavulanate potassium (125 mg) Powder Oral VİTALİS İLAÇ SAN. TİC. A.Ş. 2012-10-19 Not applicable Turkey INNOCEF PLUS 400/125 MG SAŞE, 20 ADET Cefixime trihydrate (447.63 mg) + Clavulanate potassium (125 mg) Powder Oral VİTALİS İLAÇ SAN. TİC. A.Ş. 2012-10-19 Not applicable Turkey
Categories
- ATC Codes
- J01DD08 — Cefixime
- J01DD — Third-generation cephalosporins
- J01D — OTHER BETA-LACTAM ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- J01RA — Combinations of antibacterials
- J01R — COMBINATIONS OF ANTIBACTERIALS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactams
- Sub Class
- Beta lactams
- Direct Parent
- Cephalosporins
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / 2,4-disubstituted thiazoles / 1,3-thiazines / 2-amino-1,3-thiazoles / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids / Azetidines show 9 more
- Substituents
- 1,3-thiazol-2-amine / 2,4-disubstituted 1,3-thiazole / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Azole show 23 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin (CHEBI:472657)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- XZ7BG04GJX
- CAS number
- 79350-37-1
- InChI Key
- OKBVVJOGVLARMR-QSWIMTSFSA-N
- InChI
- 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
- IUPAC Name
- (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- [H][C@]12SCC(C=C)=C(N1C(=O)[C@H]2NC(=O)C(=N/OCC(O)=O)\C1=CSC(N)=N1)C(O)=O
References
- Synthesis Reference
Pandurang Deshpande, "Process for the preparation of cefixime." U.S. Patent US20040082560, issued April 29, 2004.
US20040082560- General References
- McMillan A, Young H: The treatment of pharyngeal gonorrhoea with a single oral dose of cefixime. Int J STD AIDS. 2007 Apr;18(4):253-4. [Article]
- Adam D, Hostalek U, Troster K: 5-day cefixime therapy for bacterial pharyngitis and/or tonsillitis: comparison with 10-day penicillin V therapy. Cefixime Study Group. Infection. 1995;23 Suppl 2:S83-6. [Article]
- Leggett NJ, Caravaggio C, Rybak MJ: Cefixime. DICP. 1990 May;24(5):489-95. doi: 10.1177/106002809002400510. [Article]
- Barre J: [Pharmacokinetic properties of cefixime]. Presse Med. 1989 Oct 11;18(32):1578-82. [Article]
- Brittain DC, Scully BE, Hirose T, Neu HC: The pharmacokinetic and bactericidal characteristics of oral cefixime. Clin Pharmacol Ther. 1985 Nov;38(5):590-4. doi: 10.1038/clpt.1985.229. [Article]
- Luo Y, Helmann JD: Analysis of the role of Bacillus subtilis sigma(M) in beta-lactam resistance reveals an essential role for c-di-AMP in peptidoglycan homeostasis. Mol Microbiol. 2012 Feb;83(3):623-39. doi: 10.1111/j.1365-2958.2011.07953.x. Epub 2012 Jan 4. [Article]
- Authors unspecified: Cephalosporins. . [Article]
- Fisher JF, Mobashery S: Constructing and deconstructing the bacterial cell wall. Protein Sci. 2020 Mar;29(3):629-646. doi: 10.1002/pro.3737. Epub 2019 Nov 20. [Article]
- Bush K, Bradford PA: beta-Lactams and beta-Lactamase Inhibitors: An Overview. Cold Spring Harb Perspect Med. 2016 Aug 1;6(8). pii: cshperspect.a025247. doi: 10.1101/cshperspect.a025247. [Article]
- Sayed ARM, Shah NR, Basso KB, Kamat M, Jiao Y, Moya B, Sutaria DS, Lang Y, Tao X, Liu W, Shin E, Zhou J, Werkman C, Louie A, Drusano GL, Bulitta JB: First Penicillin-Binding Protein Occupancy Patterns for 15 beta-Lactams and beta-Lactamase Inhibitors in Mycobacterium abscessus. Antimicrob Agents Chemother. 2020 Dec 16;65(1). pii: AAC.01956-20. doi: 10.1128/AAC.01956-20. Print 2020 Dec 16. [Article]
- Mamzoridi K, Kasteridou N, Peonides A, Niopas I: Pharmacokinetics of cefixime in children with urinary tract infections after a single oral dose. Pharmacol Toxicol. 1996 Jun;78(6):417-20. doi: 10.1111/j.1600-0773.1996.tb00229.x. [Article]
- Bui T, Preuss CV: Cephalosporins. . [Article]
- Montay G, Le Liboux A, Thebault JJ, Roche G, Frydman A, Gaillot J: [Pharmacokinetics of cefixime in healthy volunteers after a single oral administration of 200 mg]. Presse Med. 1989 Oct 11;18(32):1583-6. [Article]
- Faulkner RD, Fernandez P, Lawrence G, Sia LL, Falkowski AJ, Weiss AI, Yacobi A, Silber BM: Absolute bioavailability of cefixime in man. J Clin Pharmacol. 1988 Aug;28(8):700-6. doi: 10.1002/j.1552-4604.1988.tb03203.x. [Article]
- Brogden RN, Campoli-Richards DM: Cefixime. A review of its antibacterial activity. Pharmacokinetic properties and therapeutic potential. Drugs. 1989 Oct;38(4):524-50. doi: 10.2165/00003495-198938040-00004. [Article]
- Yang KJ, Kojima N, Bristow CC, Klausner JD: Effectiveness of Cefixime for the Treatment of Neisseria gonorrhoeae Infection at 3 Anatomic Sites: A Systematic Review and Meta-Analysis. Sex Transm Dis. 2023 Mar 1;50(3):131-137. doi: 10.1097/OLQ.0000000000001742. Epub 2022 Dec 13. [Article]
- Adam D: Overview of the clinical features of cefixime. Chemotherapy. 1998 Sep;44 Suppl 1:1-5. doi: 10.1159/000048455. [Article]
- Arumugham VB, Gujarathi R, Cascella M: Third-Generation Cephalosporins. . [Article]
- Frank J. Dowd, Barton S. Johnson and Angelo J. Mariotti (2017). Pharmacology and Therapeutics for Dentistry (Seventh Edition) (7th ed.). Elsevier. [ISBN:978-0-323-39307-2]
- Kumar P. (2017). Pharmacology and therapeutics for dentistry (7th ed.). Mosby.
- FDA Approved Drug Products: SUPRAX (cefixime) for oral use, (October 2019) [Link]
- HealthLink BC: Cefixime - Oral [Link]
- Fischer Scientific: Cefixime MSDS [Link]
- Mescape: cefixime (Rx) [Link]
- External Links
- Human Metabolome Database
- HMDB0014809
- KEGG Drug
- D00258
- KEGG Compound
- C06881
- PubChem Compound
- 5362065
- PubChem Substance
- 46508684
- ChemSpider
- 4514923
- BindingDB
- 84007
- 25033
- ChEBI
- 472657
- ChEMBL
- CHEMBL1541
- ZINC
- ZINC000004468778
- Therapeutic Targets Database
- DAP000439
- PharmGKB
- PA164768821
- PDBe Ligand
- C04
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Cefixime
- PDB Entries
- 4kou
- FDA label
- Download (3.07 MB)
- MSDS
- Download (43.7 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Health Services Research Antibiotic Resistant Infection / Uncomplicated Urinary Tract Infections 1 4 Completed Treatment Gonorrhea 1 4 Recruiting Treatment Disease caused by Salmonella typhi 1 4 Unknown Status Treatment Disease caused by Salmonella typhi 1 3 Active Not Recruiting Prevention Chronic Kidney Disease (CKD) / Renal Hypodysplasia, Nonsyndromic, 1 / Vesicoureteral Reflux (VUR) 1
Pharmacoeconomics
- Manufacturers
- Lederle laboratories div american cyanamid co
- Lupin pharmaceuticals inc
- Lupin ltd
- Packagers
- A-S Medication Solutions LLC
- Dept Health Central Pharmacy
- Dispensing Solutions
- Lupin Pharmaceuticals Inc.
- Nucare Pharmaceuticals Inc.
- PD-Rx Pharmaceuticals Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Pharmedix
- Physicians Total Care Inc.
- Redpharm Drug
- Remedy Repack
- Dosage Forms
Form Route Strength Capsule Oral 400.000 mg Tablet Oral 400 mg Tablet Oral 400.00 mg Capsule Oral 200.000 mg Suspension Oral 2.000 g Suspension Oral 2.000 g Capsule, coated Oral 400 mg Powder Parenteral 100 MG/5ML Tablet, film coated Oral 200 MG Syrup Oral 2 g Tablet, film coated Oral 400 MG Powder, for suspension Oral Granule, for suspension Oral Powder, for suspension Oral 2 g Powder, for suspension Oral 100 mg/5mL Powder, for suspension Oral 200 mg/5mL Capsule Oral Powder, for suspension Oral 1 g Suspension Oral Granule Oral 100 mg Syrup Oral 100 MG/5ML Solution / drops; suspension / drops Tablet, orally disintegrating Oral 400 mg Granule Oral Tablet, film coated Oral Granule Oral 100 MG/5ML Powder Oral Tablet, orally disintegrating Oral Powder Oral 447.6 mg Powder Oral Suspension Oral Tablet, coated Oral Capsule Oral 100 MG Capsule Oral 200 MG Tablet, effervescent Syrup Oral Capsule Oral 111.19 MG Capsule Oral 223.8 MG Syrup Oral 100 mg Powder, for suspension Oral Granule, for suspension Oral 100 MG/5ML Suspension Oral 100 MG/5ML Tablet, coated Oral 400 MG Tablet, for suspension Oral 400 MG Capsule Oral 400 mg/1 Granule, for suspension Oral 2 g/100ml Powder, for solution Oral 100 mg / 5 mL Powder, for suspension Oral 100 mg / 5 mL Powder, for suspension Oral 500 mg/5mL Tablet Oral 200 mg Tablet Oral 400 mg/1 Tablet, chewable Oral 100 mg/1 Tablet, chewable Oral 200 mg/1 Tablet, coated Oral 200 MG Tablet Oral 200 mg / tab Capsule, coated Oral 52.5 mg Capsule Oral 112 MG Tablet, film coated Oral 224 MG Powder, for solution Oral 100 mg/5ml Suspension Oral 1.000 g Tablet, effervescent 100 mg Tablet, effervescent 200 mg Tablet, effervescent 400 mg Tablet Oral Syrup Oral 50 mg/5ml - Prices
Unit description Cost Unit Suprax 400 mg Tablet 3.86USD tablet Suprax 100 mg/5ml Suspension 2.8USD ml Suprax 20 mg/ml Suspension 0.45USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US9233112 No 2016-01-12 2028-12-14 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 218-225 °C https://www.fishersci.com/shop/products/cefixime-trihydrate-thermo-scientific/AAJ66094MC water solubility 55.11 mg/L http://www.sagechem.com/product/1540798 - Predicted Properties
Property Value Source Water Solubility 0.104 mg/mL ALOGPS logP 0.25 ALOGPS logP -1.3 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 2.54 Chemaxon pKa (Strongest Basic) 4.07 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 184.51 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 104.91 m3·mol-1 Chemaxon Polarizability 41.93 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.7776 Blood Brain Barrier - 0.9704 Caco-2 permeable - 0.7432 P-glycoprotein substrate Substrate 0.6934 P-glycoprotein inhibitor I Non-inhibitor 0.8863 P-glycoprotein inhibitor II Non-inhibitor 0.8724 Renal organic cation transporter Non-inhibitor 0.8301 CYP450 2C9 substrate Non-substrate 0.9002 CYP450 2D6 substrate Non-substrate 0.8161 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9029 Ames test Non AMES toxic 0.7495 Carcinogenicity Non-carcinogens 0.8549 Biodegradation Not ready biodegradable 0.9911 Rat acute toxicity 1.6878 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9897 hERG inhibition (predictor II) Non-inhibitor 0.895
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 219.82789 predictedDarkChem Lite v0.1.0 [M-H]- 188.213 predictedDeepCCS 1.0 (2019) [M+H]+ 218.83689 predictedDarkChem Lite v0.1.0 [M+H]+ 190.60857 predictedDeepCCS 1.0 (2019) [M+Na]+ 218.63639 predictedDarkChem Lite v0.1.0 [M+Na]+ 196.52109 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein group
- Organism
- Gram positive and gram negative bacteria
- Pharmacological action
- Yes
- Actions
- Binder
- General Function
- Serine-type d-ala-d-ala carboxypeptidase activity
- Specific Function
- Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
Components:
References
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Serine-type d-ala-d-ala carboxypeptidase activity
- Specific Function
- Cell wall formation; PBP-2 is responsible for the determination of the rod shape of the cell. It synthesizes cross-linked peptidoglycan from lipid intermediates.
- Gene Name
- mrdA
- Uniprot ID
- P0AD65
- Uniprot Name
- Penicillin-binding protein 2
- Molecular Weight
- 70856.1 Da
References
- Takahata S, Senju N, Osaki Y, Yoshida T, Ida T: Amino acid substitutions in mosaic penicillin-binding protein 2 associated with reduced susceptibility to cefixime in clinical isolates of Neisseria gonorrhoeae. Antimicrob Agents Chemother. 2006 Nov;50(11):3638-45. Epub 2006 Aug 28. [Article]
- Zhao S, Duncan M, Tomberg J, Davies C, Unemo M, Nicholas RA: Genetics of chromosomally mediated intermediate resistance to ceftriaxone and cefixime in Neisseria gonorrhoeae. Antimicrob Agents Chemother. 2009 Sep;53(9):3744-51. doi: 10.1128/AAC.00304-09. Epub 2009 Jun 15. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Proton-dependent oligopeptide secondary active transmembrane transporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 Da
References
- Wenzel U, Gebert I, Weintraut H, Weber WM, Clauss W, Daniel H: Transport characteristics of differently charged cephalosporin antibiotics in oocytes expressing the cloned intestinal peptide transporter PepT1 and in human intestinal Caco-2 cells. J Pharmacol Exp Ther. 1996 May;277(2):831-9. [Article]
- Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. [Article]
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
- Terada T, Saito H, Mukai M, Inui K: Characterization of stably transfected kidney epithelial cell line expressing rat H+/peptide cotransporter PEPT1: localization of PEPT1 and transport of beta-lactam antibiotics. J Pharmacol Exp Ther. 1997 Jun;281(3):1415-21. [Article]
- Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [Article]
- Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [Article]
- Tamai I, Nakanishi T, Hayashi K, Terao T, Sai Y, Shiraga T, Miyamoto K, Takeda E, Higashida H, Tsuji A: The predominant contribution of oligopeptide transporter PepT1 to intestinal absorption of beta-lactam antibiotics in the rat small intestine. J Pharm Pharmacol. 1997 Aug;49(8):796-801. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Peptide:proton symporter activity
- Specific Function
- Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
- Gene Name
- SLC15A2
- Uniprot ID
- Q16348
- Uniprot Name
- Solute carrier family 15 member 2
- Molecular Weight
- 81782.77 Da
References
- Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. [Article]
- Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [Article]
- Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [Article]
Drug created at June 13, 2005 13:24 / Updated at May 21, 2024 02:58