Cloxacillin
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Identification
- Summary
Cloxacillin is an antibiotic agent used for the treatment of beta-hemolytic streptococcal and pneumococcal infections as well as staphylococcal infections.
- Generic Name
- Cloxacillin
- DrugBank Accession Number
- DB01147
- Background
A semi-synthetic penicillin antibiotic which is a chlorinated derivative of oxacillin.
- Type
- Small Molecule
- Groups
- Approved, Investigational, Vet approved
- Structure
- Weight
- Average: 435.881
Monoisotopic: 435.065569098 - Chemical Formula
- C19H18ClN3O5S
- Synonyms
- (2S,5R,6R)-6-({[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- (3-(o-chlorophenyl)-5-methyl-4-isoxazolyl)penicillin
- 6-(3-(o-chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanic acid
- Cloxacilina
- Cloxacillin
- Cloxacilline
- Cloxacillinum
Pharmacology
- Indication
Cloxacillin is indicated for the treatment of beta-hemolytic streptococcal, pneumococcal, and staphylococcal infections (including beta-lactamase producing organisms).6
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 Infection caused by staphylococci •••••••••••• Treatment of Infections caused by penicillinase-producing staphylococci •••••••••••• Treatment of Pneumococcal infection •••••••••••• Treatment of Streptococcal infections •••••••••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
Cloxacillin is a semisynthetic antibiotic in the same class as penicillin. Cloxacillin is for use against staphylococci that produce beta-lactamase.
- Mechanism of action
By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, cloxacillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cloxacillin interferes with an autolysin inhibitor.
Target Actions Organism AD-alanyl-D-alanine carboxypeptidase DacA inhibitorEscherichia coli (strain K12) APenicillin-binding protein 2X inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) APenicillin-binding protein 1A inhibitorStreptococcus pneumoniae (strain ATCC BAA-255 / R6) - Absorption
Well absorbed from the gastrointestinal tract.
- Volume of distribution
Not Available
- Protein binding
Cloxacillin is approximately 94% protein-bound in plasma,5 primarily to albumin.3
- Metabolism
Cloxacillin, like other penicillins, appears to be metabolized via breakage of the beta-lactam ring to form an inactive penicilloic acid metabolite.2
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Oral LD50 in rat and mouse is 5000 mg/kg. Intravenous LD50 in rat is 1660 mg/kg. Symptoms of overdose include wheezing, tightness in the chest, fever, itching, bad cough, blue skin color, fits, and swelling of face, lips, tongue, or throat.
- 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 softwareAcemetacin Acemetacin may decrease the excretion rate of Cloxacillin which could result in a higher serum level. Acenocoumarol Cloxacillin may increase the anticoagulant activities of Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Cloxacillin is combined with Ambroxol. Amikacin The serum concentration of Amikacin can be decreased when it is combined with Cloxacillin. Articaine The risk or severity of methemoglobinemia can be increased when Cloxacillin is combined with Articaine. - Food Interactions
- Take on an empty stomach. Orally administered cloxacillin should be taken 1-2 hours prior to meals as the presence of food in the stomach and intestine reduces drug absorption.
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 Cloxacillin benzathine AC79L7PV2G 23736-58-5 COCFKSXGORCFOW-VZHMHXRYSA-N Cloxacillin sodium MWQ645MKMF 642-78-4 SCLZRKVZRBKZCR-SLINCCQESA-M Cloxacillin sodium hydrate 65LCB00B4Y 7081-44-9 KCUWTKOTPIUBRI-VICXVTCVSA-M - International/Other Brands
- Aclox (Southshourne) / Apo-Cloxi (Apotex) / Auropen Inj. (Cirin) / Cloxacil (Saiph) / Cloxam (MacroPhar) / Orbenin (GlaxoSmithKline) / Vaclox (Atlantic) / Vamcloxil (Vamsler)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cloxacillin Capsule 500 mg Oral Pro Doc Limitee 1994-12-31 2013-07-15 Canada Cloxacillin for Injection Powder, for solution 10 g / vial Intravenous Sterimax Inc 2013-04-03 Not applicable Canada Cloxacillin for Injection Powder, for solution 500 mg / vial Intramuscular; Intravenous Sterimax Inc 2011-09-14 Not applicable Canada Cloxacillin for Injection Powder, for solution 2 g / vial Intravenous Sterimax Inc 2011-07-28 Not applicable Canada Cloxacillin for Injection Powder, for solution 1 g / vial Intravenous Sterimax Inc 2011-07-28 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo Cloxi Cap 250mg Capsule 250 mg Oral Apotex Corporation 1984-12-31 Not applicable Canada Apo Cloxi Cap 500mg Capsule 500 mg Oral Apotex Corporation 1984-12-31 Not applicable Canada Apo Cloxi for Oral Soln 125mg/5ml Powder, for solution 125 mg / 5 mL Oral Apotex Corporation 1985-12-31 2019-12-03 Canada Jamp Cloxacillin Capsule 250 mg Oral Jamp Pharma Corporation 2022-02-17 Not applicable Canada Jamp Cloxacillin Capsule 500 mg Oral Jamp Pharma Corporation 2022-02-17 Not applicable Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image คล็อกซาติน ดรายไซรับ Powder, for suspension 125 mg/5ml Oral ห้างหุ้นส่วนจำกัด โรงงานเลิศสิงห์เภสัชกรรม 1998-02-09 Not applicable Thailand
Categories
- ATC Codes
- J01CR50 — Combinations of penicillins
- J01CR — Combinations of penicillins, incl. beta-lactamase inhibitors
- J01C — BETA-LACTAM ANTIBACTERIALS, PENICILLINS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- Beta-Lactam Antibacterials
- Beta-Lactamase Resistant Penicillins
- beta-Lactams
- Heterocyclic Compounds, Fused-Ring
- Lactams
- OAT3/SLC22A8 Inhibitors
- OAT3/SLC22A8 Substrates
- Penicillinase-resistant Penicillins
- Penicillins
- Sulfur Compounds
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Dipeptides
- Alternative Parents
- Penicillins / N-acyl-alpha amino acids and derivatives / Chlorobenzenes / Aryl chlorides / Thiazolidines / Tertiary carboxylic acid amides / Heteroaromatic compounds / Isoxazoles / Secondary carboxylic acid amides / Azetidines show 12 more
- Substituents
- Alpha-amino acid or derivatives / Alpha-dipeptide / Aromatic heteropolycyclic compound / Aryl chloride / Aryl halide / Azacycle / Azetidine / Azole / Benzenoid / Beta-lactam show 30 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- penicillin (CHEBI:49566)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- O6X5QGC2VB
- CAS number
- 61-72-3
- InChI Key
- LQOLIRLGBULYKD-JKIFEVAISA-N
- InChI
- InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1
- IUPAC Name
- (2S,5R,6R)-6-[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-amido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- SMILES
- [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl)C(O)=O
References
- Synthesis Reference
Doyle, F.P. and Nayler, J.H.C.; British Patent 905,778; September 12, 1962; assigned to Beecham Research Laboratories, Ltd. Doyle, F.P. and Nayler, J.H.C.; US. Patent 2,996,501; August 15, 1961.
- General References
- Lalanne S, Le Vee M, Lemaitre F, Le Corre P, Verdier MC, Fardel O: Differential interactions of the beta-lactam cloxacillin with human renal organic anion transporters (OATs). Fundam Clin Pharmacol. 2020 Aug;34(4):476-483. doi: 10.1111/fcp.12541. Epub 2020 Feb 25. [Article]
- Thijssen HH, Mattie H: Active metabolites of isoxazolylpencillins in humans. Antimicrob Agents Chemother. 1976 Sep;10(3):441-6. doi: 10.1128/aac.10.3.441. [Article]
- Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. doi: 10.1159/000136629. [Article]
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
- Health Canada Product Monograph: Cloxacillin sodium for oral use [Link]
- Health Canada Product Monograph: Cloxacillin sodium powder for solution for injection [Link]
- External Links
- Human Metabolome Database
- HMDB0015278
- KEGG Compound
- C06923
- PubChem Compound
- 6098
- PubChem Substance
- 46507109
- ChemSpider
- 5873
- BindingDB
- 50022788
- 2625
- ChEBI
- 49566
- ChEMBL
- CHEMBL891
- ZINC
- ZINC000003875417
- Therapeutic Targets Database
- DAP001161
- PharmGKB
- PA449059
- PDBe Ligand
- CXN
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Cloxacillin
- PDB Entries
- 9bit / 9biu
- MSDS
- Download (38 KB)
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 dataNot Available Active Not Recruiting Treatment Bacteremia Due to Methicillin Susceptible Staphylococcus Aureus 1 somestatus stop reason just information to hide Not Available Completed Prevention Double Lumen Infection / Hemodialysis Treatment 1 somestatus stop reason just information to hide Not Available Completed Treatment Cancer / Fever / Neutropenia 1 somestatus stop reason just information to hide Not Available Completed Treatment Cloxacillin Treatment / Infection / Methicillin Susceptible Staphylococcus Aureus (MSSA) Infection 1 somestatus stop reason just information to hide 4 Completed Treatment Skin Diseases, Infectious 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Apothecon
- Dispensing Solutions
- H.J. Harkins Co. Inc.
- PD-Rx Pharmaceuticals Inc.
- Teva Pharmaceutical Industries Ltd.
- Dosage Forms
Form Route Strength Powder, for suspension Oral 250 mg/5ml Injection 250 mg Injection 500 mg Powder, for suspension Oral 25 mg/mL Powder, for solution Intravenous 10 g / vial Powder, for solution Intravenous 2 g / vial Injection, powder, for solution Intramuscular; Intravenous 500 mg Powder, for solution Intramuscular; Intravenous 500 mg / vial Powder, for solution Intravenous 1 g / vial Liquid Intramuscular; Intravenous 250 mg / vial Syrup Powder, for suspension Oral 125 mg Capsule Oral Injection, powder, for solution Intramuscular; Intravenous 1 g Capsule Oral 250 mg / cap Capsule Oral 500 mg / cap Powder, for solution Intramuscular; Intravenous 2 g / vial Powder, for solution Oral 125 mg / 5 mL Granule, for suspension Oral 25 mg/mL Granule, for suspension Oral 125 mg/5ml Powder, for solution Intramuscular; Intravenous 250 mg / vial Granule, for solution Oral 125 mg Tablet, film coated 500 mg Powder, for suspension Oral 125 mg/5ml Capsule Oral 250 mg Powder 250 mg/1vial Capsule Oral 500 mg Capsule Oral 125 mg/5ml - Prices
Unit description Cost Unit Cloxacillin Sodium 2 g/vial 7.69USD vial Cloxacillin Sodium 1 g/vial 5.89USD vial Cloxacillin Sodium 500 mg/vial 4.79USD vial Apo-Cloxi 500 mg Capsule 0.38USD capsule Novo-Cloxin 500 mg Capsule 0.38USD capsule Nu-Cloxi 500 mg Capsule 0.38USD capsule Apo-Cloxi 250 mg Capsule 0.19USD capsule Novo-Cloxin 250 mg Capsule 0.19USD capsule Nu-Cloxi 250 mg Capsule 0.19USD capsule Apo-Cloxi 25 mg/ml Liquid 0.05USD ml Novo-Cloxin 25 mg/ml Liquid 0.05USD ml Nu-Cloxi 25 mg/ml Liquid 0.05USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 2.48 SANGSTER (1994) pKa 2.78 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.0532 mg/mL ALOGPS logP 2.61 ALOGPS logP 2.3 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 3.75 Chemaxon pKa (Strongest Basic) -0.41 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 112.74 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 106.64 m3·mol-1 Chemaxon Polarizability 41.64 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8368 Blood Brain Barrier - 0.9903 Caco-2 permeable - 0.8957 P-glycoprotein substrate Non-substrate 0.6204 P-glycoprotein inhibitor I Non-inhibitor 0.8951 P-glycoprotein inhibitor II Non-inhibitor 0.9204 Renal organic cation transporter Non-inhibitor 0.9629 CYP450 2C9 substrate Non-substrate 0.8262 CYP450 2D6 substrate Non-substrate 0.905 CYP450 3A4 substrate Substrate 0.5977 CYP450 1A2 substrate Inhibitor 0.8592 CYP450 2C9 inhibitor Non-inhibitor 0.891 CYP450 2D6 inhibitor Non-inhibitor 0.918 CYP450 2C19 inhibitor Non-inhibitor 0.8832 CYP450 3A4 inhibitor Non-inhibitor 0.819 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9186 Ames test Non AMES toxic 0.6979 Carcinogenicity Carcinogens 0.5672 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 1.9946 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9996 hERG inhibition (predictor II) Non-inhibitor 0.8486
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 198.0747355 predictedDarkChem Lite v0.1.0 [M-H]- 191.87189 predictedDeepCCS 1.0 (2019) [M+H]+ 199.8869355 predictedDarkChem Lite v0.1.0 [M+H]+ 194.26746 predictedDeepCCS 1.0 (2019) [M+Na]+ 198.4923355 predictedDarkChem Lite v0.1.0 [M+Na]+ 200.17998 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
- Specific Function
- beta-lactamase activity
- Gene Name
- dacA
- Uniprot ID
- P0AEB2
- Uniprot Name
- D-alanyl-D-alanine carboxypeptidase DacA
- Molecular Weight
- 44443.62 Da
References
- Nicola G, Tomberg J, Pratt RF, Nicholas RA, Davies C: Crystal structures of covalent complexes of beta-lactam antibiotics with Escherichia coli penicillin-binding protein 5: toward an understanding of antibiotic specificity. Biochemistry. 2010 Sep 21;49(37):8094-104. doi: 10.1021/bi100879m. [Article]
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- A transpeptidase that forms peptide cross-links between adjacent glycan strands in cell wall peptidoglycan (PG). Part of the divisome machinery that synthesizes the septal cross wall. Beta-lactams inactivate the PBPs by acylating an essential serine residue in the active site of these proteins.
- Specific Function
- penicillin binding
- Gene Name
- pbpX
- Uniprot ID
- P59676
- Uniprot Name
- Penicillin-binding protein 2X
- Molecular Weight
- 82342.565 Da
References
- Chittock RS, Ward S, Wilkinson AS, Caspers P, Mensch B, Page MG, Wharton CW: Hydrogen bonding and protein perturbation in beta-lactam acyl-enzymes of Streptococcus pneumoniae penicillin-binding protein PBP2x. Biochem J. 1999 Feb 15;338 ( Pt 1):153-9. [Article]
- Kind
- Protein
- Organism
- Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Cell wall formation.
- Specific Function
- penicillin binding
- Gene Name
- pbpA
- Uniprot ID
- Q8DR59
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 79700.9 Da
References
- Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Binder
- General Function
- Binds water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs (Probable). Its main function is the regulation of the colloidal osmotic pressure of blood (Probable). Major zinc transporter in plasma, typically binds about 80% of all plasma zinc (PubMed:19021548). Major calcium and magnesium transporter in plasma, binds approximately 45% of circulating calcium and magnesium in plasma (By similarity). Potentially has more than two calcium-binding sites and might additionally bind calcium in a non-specific manner (By similarity). The shared binding site between zinc and calcium at residue Asp-273 suggests a crosstalk between zinc and calcium transport in the blood (By similarity). The rank order of affinity is zinc > calcium > magnesium (By similarity). Binds to the bacterial siderophore enterobactin and inhibits enterobactin-mediated iron uptake of E.coli from ferric transferrin, and may thereby limit the utilization of iron and growth of enteric bacteria such as E.coli (PubMed:6234017). Does not prevent iron uptake by the bacterial siderophore aerobactin (PubMed:6234017)
- Specific Function
- antioxidant activity
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Albumin
- Molecular Weight
- 69365.94 Da
References
- Bratlid D, Bergan T: Displacement of albumin-bound antimicrobial agents by bilirubin. Pharmacology. 1976;14(5):464-72. doi: 10.1159/000136629. [Article]
- Friedman LA, Lewis PJ: The effect of semisynthetic penicillins on the binding of bilirubin by neonatal serum. Br J Clin Pharmacol. 1980 Jan;9(1):61-5. [Article]
- Okore VC: Effect of ascorbic acid on the binding of cloxacillin sodium to bovine serum albumin. Arzneimittelforschung. 1994 May;44(5):671-3. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- 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
- Wolman AT, Gionfriddo MR, Heindel GA, Mukhija P, Witkowski S, Bommareddy A, Vanwert AL: Organic anion transporter 3 interacts selectively with lipophilic beta-lactam antibiotics. Drug Metab Dispos. 2013 Apr;41(4):791-800. doi: 10.1124/dmd.112.049569. Epub 2013 Jan 23. [Article]
- Lalanne S, Le Vee M, Lemaitre F, Le Corre P, Verdier MC, Fardel O: Differential interactions of the beta-lactam cloxacillin with human renal organic anion transporters (OATs). Fundam Clin Pharmacol. 2020 Aug;34(4):476-483. doi: 10.1111/fcp.12541. Epub 2020 Feb 25. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- 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
- 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
- No
- 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
- 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 October 21, 2024 08:50