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Identification
- Summary
Ceftibuten is a third-generation cephalosporin antibiotic commonly used in the treatment of acute bacterial exacerbations of chronic bronchitis (ABECB), acute bacterial otitis media, pharyngitis, and tonsillitis.
- Brand Names
- Cedax
- Generic Name
- Ceftibuten
- DrugBank Accession Number
- DB01415
- Background
Ceftibuten is a third-generation cephalosporin antibiotic that is orally-administered. It is typically used to treat acute bacterial exacerbations of chronic bronchitis (ABECB), acute bacterial otitis media, pharyngitis, and tonsilitis.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Ceftibuten (DB01415)
- Weight
- Average: 410.425
Monoisotopic: 410.03547558 - Chemical Formula
- C15H14N4O6S2
- Synonyms
- (+)-(6R,7R)-7-((Z)-2-(2-amino-4-thiazolyl)-4-carboxycrotonamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
- Ceftibuten
- Ceftibutene
- Ceftibuteno
- Ceftibutenum
- cis-ceftibuten
- External IDs
- 7432-S
- SCH 39720
Pharmacology
- Indication
Indicated for the treatment of acute bacterial exacerbations of chronic bronchitis (ABECB), acute bacterial otitis media, pharyngitis, and tonsilitis.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Acute bacterial exacerbation of chronic bronchitis •••••••••••• Used in combination to treat Acute bronchitis Combination Product in combination with: Clavulanic acid (DB00766) •••••••••••• •••••• Used in combination to treat Acute otitis media Combination Product in combination with: Clavulanic acid (DB00766) •••••••••••• •••••••• •••••• Used in combination to treat Acute sinusitis Combination Product in combination with: Clavulanic acid (DB00766) •••••••••••• •••••• Treatment of Bacterial infections •••••••••••• - Contraindications & Blackbox Warnings
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Ceftibuten is an antibiotic with bactericidal actions.
- Mechanism of action
Ceftibuten exerts its bactericidal action by binding to essential target proteins of the bacterial cell wall. This binding leads to inhibition of cell-wall synthesis.
Target Actions Organism APeptidoglycan synthase FtsI inhibitorEscherichia coli (strain K12) APenicillin-binding protein 1A inhibitorEscherichia coli (strain K12) APenicillin-binding protein 1B inhibitorEscherichia coli (strain K12) APenicillin-binding protein 2 inhibitorEscherichia coli (strain K12) - Absorption
Rapidly absorbed following oral administration.
- Volume of distribution
- 0.21 L/kg [adult subjects]
- 0.5 L/kg [fasting pediatric patients]
- Protein binding
Ceftibuten is 65% bound to plasma proteins. The protein binding is independent of plasma ceftibuten concentration.
- Metabolism
A study with radiolabeled ceftibuten administered to 6 healthy adult male volunteers demonstrated that cis-ceftibuten is the predominant component in both plasma and urine. About 10% of ceftibuten is converted to the trans-isomer is approximately 1/8 as antimicrobially potent as the cis-isomer.
- Route of elimination
Ceftibuten is excreted in the urine; 95% of the administered radioactivity was recovered either in urine or feces.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Overdosage of cephalosporins can cause cerebral irritation leading to convulsions.
- 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 softwareAbacavir Ceftibuten may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Ceftibuten. Aceclofenac The risk or severity of nephrotoxicity can be increased when Ceftibuten is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Ceftibuten is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Ceftibuten is combined with Acenocoumarol. - Food Interactions
- Take separate from meals. Take ceftibuten oral suspension at least one hour after eating, or two hours before eating.
- Take with or without food. Separating the administration of ceftibuten from food is not required for ceftibuten capsules because the impact of food on bioavailability is less significant.
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 Ceftibuten dihydrate 62F4443RWP 118081-34-8 SSWTVBYDDFPFAF-DKOGRLLHSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cedax Capsule 400 mg/1 Oral Pernix Therapeutics 1995-12-20 2017-12-31 US 
Cedax Suspension 180 mg/5mL Oral Pernix Therapeutics 2010-10-20 2017-12-31 US Cedax Suspension 90 mg/5mL Oral Shionogi USA, Inc. 1995-12-01 2011-06-30 US Cedax Suspension 18 mg/1mL Oral Sciele Pharma, Inc. 1995-12-20 Not applicable US Cedax Capsule 400 mg/1 Oral Shionogi USA, Inc. 1995-12-01 2011-06-30 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ceftibuten Suspension 180 mg/5mL Oral Macoven Pharmaceuticals 2013-10-01 2017-12-31 US Ceftibuten Capsule 400 mg/1 Oral Macoven Pharmaceuticals 2013-10-01 2017-12-31 US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image BUCEF PLUS 180/62.5 MG TOZ ICEREN SASE, 20 ADET Ceftibuten dihydrate (180 mg) + Clavulanic acid (62.5 mg) Powder Oral NEUTEC İLAÇ SAN. TİC. A.Ş. 2010-12-27 Not applicable Turkey 
BUCEF PLUS 90/62.5 MG TOZ ICEREN SASE, 20 ADET Ceftibuten dihydrate (90 mg) + Clavulanic acid (62.5 mg) Powder Oral NEUTEC İLAÇ SAN. TİC. A.Ş. 2010-12-27 Not applicable Turkey WINCEF PLUS 180/62.5 MG/5 ML ORAL SUSPANSIYON HAZIRLAMAK ICIN KURU TOZ, 100 ML Ceftibuten (180 mg/5mL) + Clavulanic acid (62.5 mg/5mL) Suspension Oral CELTİS İLAÇ SAN. VE TİC. A.Ş. 2012-01-12 Not applicable Turkey WINCEF PLUS 200/62.5 MG FILM KAPLI TABLET, 20 ADET Ceftibuten (200 mg) + Clavulanic acid (62.5 mg) Tablet, coated Oral CELTİS İLAÇ SAN. VE TİC. A.Ş. 2012-02-09 Not applicable Turkey WINCEF PLUS 400/125 MG FILM KAPLI TABLET, 10 ADET Ceftibuten (400 mg) + Clavulanic acid (125 mg) Tablet, coated Oral CELTİS İLAÇ SAN. VE TİC. A.Ş. 2012-02-09 Not applicable Turkey
Categories
- ATC Codes
- J01DD14 — Ceftibuten
- Drug Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- beta-Lactams
- Cephalosporins
- Drugs that are Mainly Renally Excreted
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Nephrotoxic agents
- OAT1/SLC22A6 Substrates
- OAT3/SLC22A8 Inhibitors
- OAT3/SLC22A8 Substrates
- Sulfur Compounds
- Thiazines
- Third-Generation Cephalosporins
- 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 / N-acyl amines / Tertiary carboxylic acid amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids show 10 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 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin, dicarboxylic acid (CHEBI:3510)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- IW71N46B4Y
- CAS number
- 97519-39-6
- InChI Key
- UNJFKXSSGBWRBZ-BJCIPQKHSA-N
- InChI
- InChI=1S/C15H14N4O6S2/c16-15-17-7(5-27-15)6(1-2-9(20)21)11(22)18-10-12(23)19-8(14(24)25)3-4-26-13(10)19/h1,3,5,10,13H,2,4H2,(H2,16,17)(H,18,22)(H,20,21)(H,24,25)/b6-1-/t10-,13-/m1/s1
- IUPAC Name
- (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-4-carboxybut-2-enamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- [H][C@]12SCC=C(N1C(=O)[C@H]2NC(=O)C(=C/CC(O)=O)\C1=CSC(N)=N1)C(O)=O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015485
- KEGG Drug
- D00922
- KEGG Compound
- C08117
- PubChem Compound
- 5282242
- PubChem Substance
- 46507324
- ChemSpider
- 4445419
- BindingDB
- 50370586
- 20492
- ChEBI
- 3510
- ChEMBL
- CHEMBL1605
- ZINC
- ZINC000003871967
- Therapeutic Targets Database
- DAP000456
- PharmGKB
- PA164744555
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Ceftibuten
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data3 Terminated Treatment Pyelonephritis 1 somestatus stop reason just information to hide 1 Completed Basic Science Healthy Volunteers (HV) 2 somestatus stop reason just information to hide 1 Completed Basic Science Pharmacokinetics 1 somestatus stop reason just information to hide 1 Completed Treatment Pharmacokinetics 1 somestatus stop reason just information to hide 1 Not Yet Recruiting Treatment Bacterial Infections 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Schering Corp.
- Sciele Pharma Inc.
- Shionogi Pharma Inc.
- Zyber Pharmaceuticals
- Dosage Forms
Form Route Strength Powder Oral Powder Oral Capsule Oral 200 MG Capsule Oral 400 mg/1 Capsule Oral 400 MG Capsule Oral 400.00 mg Granule, for suspension Oral 14.4 g/100g Suspension Oral 18 mg/1mL Suspension Oral 2.1600 g Suspension Oral 90 mg/5mL Tablet, effervescent Suspension Oral 180 mg/5mL Powder, for suspension Oral 3.6 g Capsule Oral 400.000 mg Suspension Oral 3.600 g Granule, for suspension Oral 200 mg Granule, for suspension Oral 36 mg/mL Granule, for suspension Oral 400 mg Suspension Oral 36 mg/ml Capsule Oral Granule, for suspension Oral Tablet, film coated 200 mg Tablet, film coated 400 mg Suspension Oral Tablet, coated Oral Capsule Oral 435.120 mg - Prices
Unit description Cost Unit Cedax 400 mg capsule 16.13USD capsule DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5599557 No 1997-02-04 2014-02-04 US US4634697 No 1987-01-06 2009-10-01 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0705 mg/mL ALOGPS logP 0.31 ALOGPS logP -1.5 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 2.85 Chemaxon pKa (Strongest Basic) 4.68 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 162.92 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 97.02 m3·mol-1 Chemaxon Polarizability 38.49 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 - 0.5755 Blood Brain Barrier - 0.9679 Caco-2 permeable - 0.8957 P-glycoprotein substrate Substrate 0.5424 P-glycoprotein inhibitor I Non-inhibitor 0.9274 P-glycoprotein inhibitor II Non-inhibitor 0.9586 Renal organic cation transporter Non-inhibitor 0.929 CYP450 2C9 substrate Non-substrate 0.8531 CYP450 2D6 substrate Non-substrate 0.8293 CYP450 3A4 substrate Non-substrate 0.6007 CYP450 1A2 substrate Non-inhibitor 0.8787 CYP450 2C9 inhibitor Non-inhibitor 0.8817 CYP450 2D6 inhibitor Non-inhibitor 0.9191 CYP450 2C19 inhibitor Non-inhibitor 0.8833 CYP450 3A4 inhibitor Non-inhibitor 0.9625 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9387 Ames test Non AMES toxic 0.7274 Carcinogenicity Non-carcinogens 0.8961 Biodegradation Not ready biodegradable 0.9688 Rat acute toxicity 1.6446 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9848 hERG inhibition (predictor II) Non-inhibitor 0.9305
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00l6-4429000000-9eb742eca3a39f7f33c7 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-01q9-0902600000-c2388ee87fe4a0c57f08 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-01b9-0219000000-190493c1b5a3aa9e4571 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0j5c-0392000000-5e8978fc10ac139bd0fa Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0079-0129000000-be37f9cbf73c4ef955d4 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001c-9618000000-8887fe2fa2644176a32c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-05tf-0942000000-0dc6c5afe7b099d98aaa Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 191.9374743 predictedDarkChem Lite v0.1.0 [M-H]- 200.9991743 predictedDarkChem Lite v0.1.0 [M-H]- 185.77048 predictedDeepCCS 1.0 (2019) [M+H]+ 190.5948743 predictedDarkChem Lite v0.1.0 [M+H]+ 200.9544743 predictedDarkChem Lite v0.1.0 [M+H]+ 188.16603 predictedDeepCCS 1.0 (2019) [M+Na]+ 190.8420743 predictedDarkChem Lite v0.1.0 [M+Na]+ 201.3120743 predictedDarkChem Lite v0.1.0 [M+Na]+ 194.31775 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Peptidoglycan glycosyltransferase activity
- Specific Function
- Essential cell division protein that is required for the synthesis of peptidoglycan at the division septum (PubMed:1103132, PubMed:9614966). Catalyzes the synthesis of cross-linked peptidoglycan fr...
- Gene Name
- ftsI
- Uniprot ID
- P0AD68
- Uniprot Name
- Peptidoglycan synthase FtsI
- Molecular Weight
- 63876.925 Da
References
- Wise R, Andrews JM, Ashby JP, Thornber D: Ceftibuten--in-vitro activity against respiratory pathogens, beta-lactamase stability and mechanism of action. J Antimicrob Chemother. 1990 Aug;26(2):209-13. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serine-type d-ala-d-ala carboxypeptidase activity
- Specific Function
- Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
- Gene Name
- mrcA
- Uniprot ID
- P02918
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 93635.545 Da
References
- Wise R, Andrews JM, Ashby JP, Thornber D: Ceftibuten--in-vitro activity against respiratory pathogens, beta-lactamase stability and mechanism of action. J Antimicrob Chemother. 1990 Aug;26(2):209-13. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Serine-type d-ala-d-ala carboxypeptidase activity
- Specific Function
- Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
- Gene Name
- mrcB
- Uniprot ID
- P02919
- Uniprot Name
- Penicillin-binding protein 1B
- Molecular Weight
- 94291.875 Da
References
- Wise R, Andrews JM, Ashby JP, Thornber D: Ceftibuten--in-vitro activity against respiratory pathogens, beta-lactamase stability and mechanism of action. J Antimicrob Chemother. 1990 Aug;26(2):209-13. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- 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
- Wise R, Andrews JM, Ashby JP, Thornber D: Ceftibuten--in-vitro activity against respiratory pathogens, beta-lactamase stability and mechanism of action. J Antimicrob Chemother. 1990 Aug;26(2):209-13. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Electrogenic proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides. Transports neutral and monovalently charged peptides with a proton to peptide stoichiometry of 1:1 or 2:1 (By similarity) (PubMed:15521010, PubMed:18367661, PubMed:19685173, PubMed:26320580, PubMed:7896779, PubMed:8914574, PubMed:9835627). Primarily responsible for the absorption of dietary di- and tripeptides from the small intestinal lumen (By similarity). Mediates transepithelial transport of muramyl and N-formylated bacterial dipeptides contributing to recognition of pathogenic bacteria by the mucosal immune system (PubMed:15521010, PubMed:9835627)
- Specific Function
- Dipeptide transmembrane transporter activity
- Gene Name
- SLC15A1
- Uniprot ID
- P46059
- Uniprot Name
- Solute carrier family 15 member 1
- Molecular Weight
- 78805.265 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]
- 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]
- Saito H, Okuda M, Terada T, Sasaki S, Inui K: Cloning and characterization of a rat H+/peptide cotransporter mediating absorption of beta-lactam antibiotics in the intestine and kidney. J Pharmacol Exp Ther. 1995 Dec;275(3):1631-7. [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]
- Menon RM, Barr WH: Transporters involved in apical and basolateral uptake of ceftibuten into Caco-2 cells. Biopharm Drug Dispos. 2002 Nov;23(8):317-26. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Proton-coupled amino-acid transporter that transports oligopeptides of 2 to 4 amino acids with a preference for dipeptides (PubMed:16434549, PubMed:18367661, PubMed:7756356). Transports neutral and anionic dipeptides with a proton to peptide stoichiometry of 2:1 or 3:1 (By similarity). In kidney, involved in the absorption of circulating di- and tripeptides from the glomerular filtrate (PubMed:7756356). Can also transport beta-lactam antibiotics, such as the aminocephalosporin cefadroxil, and other antiviral and anticancer drugs (PubMed:16434549). Transports the dipeptide-like aminopeptidase inhibitor bestatin (By similarity). Also able to transport carnosine (PubMed:31073693). Involved in innate immunity by promoting the detection of microbial pathogens by NOD-like receptors (NLRs) (By similarity). Mediates transport of bacterial peptidoglycans across the plasma membrane or, in macrophages, the phagosome membrane: catalyzes the transport of certain bacterial peptidoglycans, such as muramyl dipeptide (MDP), the NOD2 ligand (PubMed:20406817)
- Specific Function
- Dipeptide transmembrane transporter activity
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- Curator comments
- Substrate profile was investigated in in vitro studies using HEK293 cells.
- General Function
- Secondary active transporter that functions as a Na(+)-independent organic anion (OA)/dicarboxylate antiporter where the uptake of one molecule of OA into the cell is coupled with an efflux of one molecule of intracellular dicarboxylate such as 2-oxoglutarate or glutarate (PubMed:11669456, PubMed:11907186, PubMed:14675047, PubMed:22108572, PubMed:23832370, PubMed:28534121, PubMed:9950961). Mediates the uptake of OA across the basolateral side of proximal tubule epithelial cells, thereby contributing to the renal elimination of endogenous OA from the systemic circulation into the urine (PubMed:9887087). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). Transports prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) and may contribute to their renal excretion (PubMed:11907186). Also mediates the uptake of cyclic nucleotides such as cAMP and cGMP (PubMed:26377792). Involved in the transport of neuroactive tryptophan metabolites kynurenate (KYNA) and xanthurenate (XA) and may contribute to their secretion from the brain (PubMed:22108572, PubMed:23832370). May transport glutamate (PubMed:26377792). Also involved in the disposition of uremic toxins and potentially toxic xenobiotics by the renal organic anion secretory pathway, helping reduce their undesired toxicological effects on the body (PubMed:11669456, PubMed:14675047). Uremic toxins include the indoxyl sulfate (IS), hippurate/N-benzoylglycine (HA), indole acetate (IA), 3-carboxy-4- methyl-5-propyl-2-furanpropionate (CMPF) and urate (PubMed:14675047, PubMed:26377792). Xenobiotics include the mycotoxin ochratoxin (OTA) (PubMed:11669456). May also contribute to the transport of organic compounds in testes across the blood-testis-barrier (PubMed:35307651)
- Specific Function
- Alpha-ketoglutarate transmembrane transporter activity
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- Curator comments
- Substrate and inhibitor profile was investigated in vitro using human OAT3 expressed on HEK293 cells.
- General Function
- Functions as an organic anion/dicarboxylate exchanger that couples organic anion uptake indirectly to the sodium gradient (PubMed:14586168, PubMed:15644426, PubMed:15846473, PubMed:16455804, PubMed:31553721). Transports organic anions such as estrone 3-sulfate (E1S) and urate in exchange for dicarboxylates such as glutarate or ketoglutarate (2-oxoglutarate) (PubMed:14586168, PubMed:15846473, PubMed:15864504, PubMed:22108572, PubMed:23832370). Plays an important role in the excretion of endogenous and exogenous organic anions, especially from the kidney and the brain (PubMed:11306713, PubMed:14586168, PubMed:15846473). E1S transport is pH- and chloride-dependent and may also involve E1S/cGMP exchange (PubMed:26377792). Responsible for the transport of prostaglandin E2 (PGE2) and prostaglandin F2(alpha) (PGF2(alpha)) in the basolateral side of the renal tubule (PubMed:11907186). Involved in the transport of neuroactive tryptophan metabolites kynurenate and xanthurenate (PubMed:22108572, PubMed:23832370). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). May be involved in the basolateral transport of steviol, a metabolite of the popular sugar substitute stevioside (PubMed:15644426). May participate in the detoxification/ renal excretion of drugs and xenobiotics, such as the histamine H(2)-receptor antagonists fexofenadine and cimetidine, the antibiotic benzylpenicillin (PCG), the anionic herbicide 2,4-dichloro-phenoxyacetate (2,4-D), the diagnostic agent p-aminohippurate (PAH), the antiviral acyclovir (ACV), and the mycotoxin ochratoxin (OTA), by transporting these exogenous organic anions across the cell membrane in exchange for dicarboxylates such as 2-oxoglutarate (PubMed:11669456, PubMed:15846473, PubMed:16455804). Contributes to the renal uptake of potent uremic toxins (indoxyl sulfate (IS), indole acetate (IA), hippurate/N-benzoylglycine (HA) and 3-carboxy-4-methyl-5-propyl-2-furanpropionate (CMPF)), pravastatin, PCG, E1S and dehydroepiandrosterone sulfate (DHEAS), and is partly involved in the renal uptake of temocaprilat (an angiotensin-converting enzyme (ACE) inhibitor) (PubMed:14675047). May contribute to the release of cortisol in the adrenals (PubMed:15864504). Involved in one of the detoxification systems on the choroid plexus (CP), removes substrates such as E1S or taurocholate (TC), PCG, 2,4-D and PAH, from the cerebrospinal fluid (CSF) to the blood for eventual excretion in urine and bile (By similarity). Also contributes to the uptake of several other organic compounds such as the prostanoids prostaglandin E(2) and prostaglandin F(2-alpha), L-carnitine, and the therapeutic drugs allopurinol, 6-mercaptopurine (6-MP) and 5-fluorouracil (5-FU) (By similarity). Mediates the transport of PAH, PCG, and the statins pravastatin and pitavastatin, from the cerebrum into the blood circulation across the blood-brain barrier (BBB). In summary, plays a role in the efflux of drugs and xenobiotics, helping reduce their undesired toxicological effects on the body (By similarity)
- Specific Function
- Organic anion transmembrane transporter activity
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Organic anion transporter 3
- Molecular Weight
- 59855.585 Da
References
- VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [Article]
Drug created at July 23, 2007 13:06 / Updated at June 02, 2024 21:53