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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAcute exacerbation of chronic bronchitis caused by streptococcus pneumoniae•••••••••••••••••••• ••••••••••• ••••••• ••••••• ••••••••
Treatment ofAcute exacerbations of chronic bronchitis caused by haemophilus influenzae•••••••••••••••••••• ••••••••••• ••••••• ••••••• ••••••••
Treatment ofCommunity acquired pneumonia••• •••••
Treatment ofGonorrhea of anus••• •••••
Treatment ofLyme disease••• •••••
Contraindications & Blackbox Warnings
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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

TargetActionsOrganism
APenicillin-binding protein
binder
Gram positive and gram negative bacteria
UPenicillin-binding protein 2Not AvailableEscherichia 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.
DrugInteraction
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Cefixime.
AcenocoumarolThe risk or severity of bleeding can be increased when Cefixime is combined with Acenocoumarol.
AlteplaseThe therapeutic efficacy of Alteplase can be decreased when used in combination with Cefixime.
AmbroxolThe risk or severity of methemoglobinemia can be increased when Cefixime is combined with Ambroxol.
AncrodThe 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

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Product Ingredients
IngredientUNIICASInChI Key
Cefixime trihydrate97I1C92E55125110-14-7IPYWNMVPZOAFOQ-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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
SupraxCapsule400 mg/1OralPD-Rx Pharmaceuticals, Inc.2013-03-15Not applicableUS flag
SupraxTablet400 mgOralOdan Laboratories Ltd1990-12-31Not applicableCanada flag
SupraxCapsule400 mg/1OralRemedy Repack2018-02-022018-02-02US flag
SupraxCapsule400 mg/1OralLUPIN LIMITED2013-03-152018-12-03US flag
SupraxPowder, for solution100 mg / 5 mLOralAventis Pharma Ltd.1990-12-312005-12-07Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Auro-cefiximePowder, for suspension100 mg / 5 mLOralAuro Pharma Inc2018-01-08Not applicableCanada flag
Auro-cefiximeTablet400 mgOralAuro Pharma Inc2014-10-24Not applicableCanada flag
CefiximePowder, for suspension200 mg/5mLOralLupin Pharmaceuticals, Inc.2015-04-24Not applicableUS flag
CefiximePowder, for suspension200 mg/5mLOralDr. Reddy’s Laboratories, Inc2017-08-03Not applicableUS flag
CefiximePowder, for suspension200 mg/5mLOralBelcher Pharmaceuticals,LLC2017-03-15Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
INNOCEF PLUS 100/62.5 MG SASE, 20 ADETCefixime trihydrate (111.9 mg) + Clavulanate potassium (62.5 mg)PowderOralVİTALİS İLAÇ SAN. TİC. A.Ş.2011-11-11Not applicableTurkey flag
INNOCEF PLUS 200/125 MG SAŞE, 20 ADETCefixime trihydrate (223.8 mg) + Clavulanate potassium (125 mg)PowderOralVİTALİS İLAÇ SAN. TİC. A.Ş.2012-10-19Not applicableTurkey flag
INNOCEF PLUS 200/62.5 MG SASE, 20 ADETCefixime trihydrate (223.8 mg) + Clavulanate potassium (62.5 mg)PowderOralVİTALİS İLAÇ SAN. TİC. A.Ş.2011-11-04Not applicableTurkey flag
INNOCEF PLUS 400/125 MG SAŞE, 10 ADETCefixime trihydrate (447.63 mg) + Clavulanate potassium (125 mg)PowderOralVİTALİS İLAÇ SAN. TİC. A.Ş.2012-10-19Not applicableTurkey flag
INNOCEF PLUS 400/125 MG SAŞE, 20 ADETCefixime trihydrate (447.63 mg) + Clavulanate potassium (125 mg)PowderOralVİTALİS İLAÇ SAN. TİC. A.Ş.2012-10-19Not applicableTurkey flag

Categories

ATC Codes
J01DD08 — CefiximeJ01RA16 — Cefixime and azithromycinJ01RA15 — Cefixime and ornidazole
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
  1. 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]
  2. 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]
  3. Leggett NJ, Caravaggio C, Rybak MJ: Cefixime. DICP. 1990 May;24(5):489-95. doi: 10.1177/106002809002400510. [Article]
  4. Barre J: [Pharmacokinetic properties of cefixime]. Presse Med. 1989 Oct 11;18(32):1578-82. [Article]
  5. 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]
  6. 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]
  7. Authors unspecified: Cephalosporins. . [Article]
  8. 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]
  9. 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]
  10. 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]
  11. 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]
  12. Bui T, Preuss CV: Cephalosporins. . [Article]
  13. 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]
  14. 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]
  15. 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]
  16. 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]
  17. Adam D: Overview of the clinical features of cefixime. Chemotherapy. 1998 Sep;44 Suppl 1:1-5. doi: 10.1159/000048455. [Article]
  18. Arumugham VB, Gujarathi R, Cascella M: Third-Generation Cephalosporins. . [Article]
  19. 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]
  20. Kumar P. (2017). Pharmacology and therapeutics for dentistry (7th ed.). Mosby.
  21. FDA Approved Drug Products: SUPRAX (cefixime) for oral use, (October 2019) [Link]
  22. HealthLink BC: Cefixime - Oral [Link]
  23. Fischer Scientific: Cefixime MSDS [Link]
  24. Mescape: cefixime (Rx) [Link]
Human Metabolome Database
HMDB0014809
KEGG Drug
D00258
KEGG Compound
C06881
PubChem Compound
5362065
PubChem Substance
46508684
ChemSpider
4514923
BindingDB
84007
RxNav
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
PhaseStatusPurposeConditionsCount
4CompletedHealth Services ResearchAntibiotic Resistant Infection / Uncomplicated Urinary Tract Infections1
4CompletedTreatmentGonorrhea1
4RecruitingTreatmentDisease caused by Salmonella typhi1
4Unknown StatusTreatmentDisease caused by Salmonella typhi1
3Active Not RecruitingPreventionChronic 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
FormRouteStrength
CapsuleOral400.000 mg
TabletOral400 mg
TabletOral400.00 mg
CapsuleOral200.000 mg
SuspensionOral2.000 g
SuspensionOral2.000 g
Capsule, coatedOral400 mg
PowderParenteral100 MG/5ML
Tablet, film coatedOral200 MG
SyrupOral2 g
Tablet, film coatedOral400 MG
Powder, for suspensionOral
Granule, for suspensionOral
Powder, for suspensionOral2 g
Powder, for suspensionOral100 mg/5mL
Powder, for suspensionOral200 mg/5mL
CapsuleOral
Powder, for suspensionOral1 g
SuspensionOral
GranuleOral100 mg
SyrupOral100 MG/5ML
Solution / drops; suspension / drops
Tablet, orally disintegratingOral400 mg
GranuleOral
Tablet, film coatedOral
GranuleOral100 MG/5ML
PowderOral
Tablet, orally disintegratingOral
PowderOral447.6 mg
PowderOral
SuspensionOral
Tablet, coatedOral
CapsuleOral100 MG
CapsuleOral200 MG
Tablet, effervescent
SyrupOral
CapsuleOral111.19 MG
CapsuleOral223.8 MG
SyrupOral100 mg
Powder, for suspensionOral
Granule, for suspensionOral100 MG/5ML
SuspensionOral100 MG/5ML
Tablet, coatedOral400 MG
Tablet, for suspensionOral400 MG
CapsuleOral400 mg/1
Granule, for suspensionOral2 g/100ml
Powder, for solutionOral100 mg / 5 mL
Powder, for suspensionOral100 mg / 5 mL
Powder, for suspensionOral500 mg/5mL
TabletOral200 mg
TabletOral400 mg/1
Tablet, chewableOral100 mg/1
Tablet, chewableOral200 mg/1
Tablet, coatedOral200 MG
TabletOral200 mg / tab
Capsule, coatedOral52.5 mg
CapsuleOral112 MG
Tablet, film coatedOral224 MG
Powder, for solutionOral100 mg/5ml
SuspensionOral1.000 g
Tablet, effervescent100 mg
Tablet, effervescent200 mg
Tablet, effervescent400 mg
TabletOral
SyrupOral50 mg/5ml
Prices
Unit descriptionCostUnit
Suprax 400 mg Tablet3.86USD tablet
Suprax 100 mg/5ml Suspension2.8USD ml
Suprax 20 mg/ml Suspension0.45USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US9233112No2016-01-122028-12-14US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)218-225 °Chttps://www.fishersci.com/shop/products/cefixime-trihydrate-thermo-scientific/AAJ66094MC
water solubility55.11 mg/Lhttp://www.sagechem.com/product/1540798
Predicted Properties
PropertyValueSource
Water Solubility0.104 mg/mLALOGPS
logP0.25ALOGPS
logP-1.3Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)2.54Chemaxon
pKa (Strongest Basic)4.07Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area184.51 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity104.91 m3·mol-1Chemaxon
Polarizability41.93 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.7776
Blood Brain Barrier-0.9704
Caco-2 permeable-0.7432
P-glycoprotein substrateSubstrate0.6934
P-glycoprotein inhibitor INon-inhibitor0.8863
P-glycoprotein inhibitor IINon-inhibitor0.8724
Renal organic cation transporterNon-inhibitor0.8301
CYP450 2C9 substrateNon-substrate0.9002
CYP450 2D6 substrateNon-substrate0.8161
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9029
Ames testNon AMES toxic0.7495
CarcinogenicityNon-carcinogens0.8549
BiodegradationNot ready biodegradable0.9911
Rat acute toxicity1.6878 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9897
hERG inhibition (predictor II)Non-inhibitor0.895
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0pb9-9272800000-e2d11677dac795ff2b58
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-004i-3920000000-3269e737530417831893
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-3920000000-3269e737530417831893
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f79-0112900000-d16acf72b7612af9d9ec
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-1090200000-31d9df7b46596fce268d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bu9-0449800000-f52168c67a7714d509b6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-06di-2873900000-f8b92e53314f06bbc09f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0229100000-2737637db44bec0b3d03
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00b9-3902100000-dd1ae51ad0b22675c2b0
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-219.82789
predicted
DarkChem Lite v0.1.0
[M-H]-188.213
predicted
DeepCCS 1.0 (2019)
[M+H]+218.83689
predicted
DarkChem Lite v0.1.0
[M+H]+190.60857
predicted
DeepCCS 1.0 (2019)
[M+Na]+218.63639
predicted
DarkChem Lite v0.1.0
[M+Na]+196.52109
predicted
DeepCCS 1.0 (2019)

Targets

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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
  1. Authors unspecified: Cephalosporins. . [Article]
  2. Bui T, Preuss CV: Cephalosporins. . [Article]
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
  1. 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]
  2. 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
Substrate
Inhibitor
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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [Article]
  7. 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
  1. 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]
  2. 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]
  3. 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 29, 2024 19:09