Explore a selection of our essential drug information below, or:
Identification
- Summary
Piroxicam is an NSAID used to treat the symptoms of osteoarthritis and rheumatoid arthritis.
- Brand Names
- Feldene
- Generic Name
- Piroxicam
- DrugBank Accession Number
- DB00554
- Background
A cyclooxygenase inhibiting, non-steroidal anti-inflammatory agent (NSAID) that is well established in treating rheumatoid arthritis and osteoarthritis and used for musculoskeletal disorders, dysmenorrhea, and postoperative pain. Its long half-life enables it to be administered once daily.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Piroxicam (DB00554)
- Weight
- Average: 331.346
Monoisotopic: 331.062676609 - Chemical Formula
- C15H13N3O4S
- Synonyms
- 4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazin-3-caboxyamid-1,1-dioxid
- Piroxicam
- Piroxicam betadex
- Piroxicamum
- Pyroxycam
- External IDs
- CP-16,171
Pharmacology
- Indication
For treatment of osteoarthritis and rheumatoid arthritis.
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 Symptomatic treatment of Ankylosing spondylitis •••••••••••• Symptomatic treatment of Osteoarthritis •••••••••••• Symptomatic treatment of Rheumatoid arthritis •••••••••••• - 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
Piroxicam is in a class of drugs called nonsteroidal anti-inflammatory drugs (NSAIDs). Piroxicam works by reducing hormones that cause inflammation and pain in the body. Piroxicam is used to reduce the pain, inflammation, and stiffness caused by rheumatoid arthritis and osteoarthritis.
- Mechanism of action
The antiinflammatory effect of Piroxicam may result from the reversible inhibition of cyclooxygenase, causing the peripheral inhibition of prostaglandin synthesis. The prostaglandins are produced by an enzyme called Cox-1. Piroxicam blocks the Cox-1 enzyme, resulting into the disruption of production of prostaglandins. Piroxicam also inhibits the migration of leukocytes into sites of inflammation and prevents the formation of thromboxane A2, an aggregating agent, by the platelets.
Target Actions Organism AProstaglandin G/H synthase 2 inhibitorHumans UProstaglandin G/H synthase 1 inhibitorHumans - Absorption
Well absorbed following oral administration.
- Volume of distribution
- 0.14 L/kg
- Protein binding
Not Available
- Metabolism
Renal
Hover over products below to view reaction partners
- Route of elimination
Piroxicam and its biotransformation products are excreted in urine and feces, with about twice as much appearing in the urine as in the feces. Approximately 5% of a piroxicam dose is excreted unchanged. However, a substantial portion of piroxicam elimination occurs by hepatic metabolism. Piroxicam is excreted into human milk.
- Half-life
30 to 86 hours
- 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
Symptoms of overdose include drowsiness, nausea, stomach pain, and/or vomiting.
- Pathways
Pathway Category Piroxicam Action Pathway Drug action - Pharmacogenomic Effects/ADRs
Interacting Gene/Enzyme Allele name Genotype(s) Defining Change(s) Type(s) Description Details Cytochrome P450 2C9 CYP2C9*2 Not Available 430C>T Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*3 Not Available 1075A>C Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*4 Not Available 1076T>C Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*5 Not Available 1080C>G Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*8 Not Available 449G>A Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*11 Not Available 1003C>T Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*12 Not Available 1465C>T Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*13 Not Available 269T>C Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*14 Not Available 374G>A Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*16 Not Available 895A>G Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*18 Not Available 1075A>C / 1190A>C … show all Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*26 Not Available 389C>G Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*28 Not Available 641A>T Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*30 Not Available 1429G>A Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*33 Not Available 395G>A Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*6 Not Available 818delA Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*15 Not Available 485C>A Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*25 Not Available 353_362delAGAAATGGAA Effect Inferred Poor drug metabolizer, lower dose requirement. Details Cytochrome P450 2C9 CYP2C9*35 Not Available 374G>T / 430C>T Effect Inferred Poor drug metabolizer, lower dose requirement. Details
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 Piroxicam may decrease the excretion rate of Abacavir which could result in a higher serum level. Abatacept The metabolism of Piroxicam can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Piroxicam is combined with Abciximab. Abiraterone The metabolism of Piroxicam can be decreased when combined with Abiraterone. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Piroxicam. - Food Interactions
- Avoid alcohol.
- Take with food.
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 Images
- International/Other Brands
- Bruxicam / Dolonex / Erazon / Geldène / Improntal / Roxam (Bosnalijek) / Roxiden / Sasulen / Solocalm / Trast
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Feldene Capsule 20 mg/1 Oral Physicians Total Care, Inc. 1994-05-25 2012-06-30 US 
Feldene Capsule 10 mg/1 Oral Pfizer Laboratories Div Pfizer Inc 1994-05-25 2024-01-31 US Feldene Capsule 20 mg/1 Oral Remedy Repack 2012-07-19 2013-08-20 US Feldene Capsule 20 mg/1 Oral Pfizer Laboratories Div Pfizer Inc 1994-05-25 2024-06-30 US Feldene Cap 10mg Capsule 10 mg Oral Pfizer Canada Ulc 1981-12-31 2002-09-06 Canada 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Alti-piroxicam-cap 10mg Capsule 10 mg / cap Oral Altimed Pharma Inc. 1997-09-24 2004-08-03 Canada Alti-piroxicam-cap 20mg Capsule 20 mg / cap Oral Altimed Pharma Inc. 1995-12-31 2004-08-03 Canada Apo Piroxicam Cap 10mg Capsule 10 mg Oral Apotex Corporation 1986-12-31 Not applicable Canada Apo Piroxicam Cap 20mg Capsule 20 mg Oral Apotex Corporation 1986-12-31 Not applicable Canada Dom-piroxicam Capsule 10 mg Oral Dominion Pharmacal Not applicable 2016-10-25 Canada - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image FELDENE (0.5% GEL) Gel 0.5 %w/w Topical บริษัท ไฟเซอร์ (ประเทศไทย) จำกัด 2006-12-04 Not applicable Thailand 
PREDENE GEL Gel 0.5 %w/w Topical บริษัท โรงงานเภสัชกรรมแอตแลนติค จำกัด 2009-07-31 Not applicable Thailand ROSIDEN GEL Gel 5 mg/g Topical ZYFAS PHARMA PTE LTD 1990-03-10 Not applicable Singapore 
ROXIFEN GEL 500 mg/100 g Gel 500 mg/100g Topical JOYSON PTE. LTD. 1999-05-06 Not applicable Singapore ค็อกซ์ซิแคม เจล Gel 0.5 %w/w Topical บริษัท โรงงานเภสัชอุตสาหกรรม เจเอสพี (ประเทศไทย) จำกัด (มหาชน) 2017-08-18 2020-09-29 Thailand - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Therafeldamine Piroxicam (20 mg/1) + gamma-Aminobutyric acid (100 mg/1) Kit Oral Physician Therapeutics Llc 2011-03-03 Not applicable US
Categories
- ATC Codes
- M01AC01 — Piroxicam
- M01AC — Oxicams
- M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
- M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
- M — MUSCULO-SKELETAL SYSTEM
- M02AA — Antiinflammatory preparations, non-steroids for topical use
- M02A — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
- M02 — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
- M — MUSCULO-SKELETAL SYSTEM
- Drug Categories
- Agents causing hyperkalemia
- Agents that produce hypertension
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Anti-Inflammatory Agents, Non-Steroidal (Non-Selective)
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Antiinflammatory Preparations, Non-Steroids for Topical Use
- Antirheumatic Agents
- Cyclooxygenase Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Drugs causing inadvertant photosensitivity
- Drugs that are Mainly Renally Excreted
- Enzyme Inhibitors
- Musculo-Skeletal System
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- OAT1/SLC22A6 inhibitors
- OAT3/SLC22A8 Inhibitors
- Ophthalmologicals
- Organic Anion Transporting Polypeptide 2B1 Inhibitors
- Other Nonsteroidal Anti-inflammatory Agents
- Oxicams
- Peripheral Nervous System Agents
- Photosensitizing Agents
- Sensory Organs
- Sensory System Agents
- Sulfur Compounds
- Thiazines
- Topical Products for Joint and Muscular Pain
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzothiazines
- Sub Class
- Not Available
- Direct Parent
- Benzothiazines
- Alternative Parents
- Alpha amino acids and derivatives / Pyridines and derivatives / Organosulfonamides / 1,2-thiazines / Benzenoids / Imidolactams / Heteroaromatic compounds / Secondary carboxylic acid amides / Azacyclic compounds / Carboximidic acids show 6 more
- Substituents
- Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzothiazine / Carbonyl group / Carboximidic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative show 14 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- monocarboxylic acid amide, pyridines, benzothiazine (CHEBI:8249)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 13T4O6VMAM
- CAS number
- 36322-90-4
- InChI Key
- QYSPLQLAKJAUJT-UHFFFAOYSA-N
- InChI
- InChI=1S/C15H13N3O4S/c1-18-13(15(20)17-12-8-4-5-9-16-12)14(19)10-6-2-3-7-11(10)23(18,21)22/h2-9,19H,1H3,(H,16,17,20)
- IUPAC Name
- 4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1lambda6,2-benzothiazine-3-carboxamide
- SMILES
- CN1C(C(=O)NC2=NC=CC=C2)=C(O)C2=C(C=CC=C2)S1(=O)=O
References
- Synthesis Reference
Paul D. Weeks, "3-Hydroxy 2-methyl benzisothiazolines as intermediates in production of piroxicam." U.S. Patent US4376204, issued April, 1982.
US4376204- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014694
- KEGG Drug
- D00127
- KEGG Compound
- C01608
- PubChem Compound
- 54676228
- PubChem Substance
- 46505225
- ChemSpider
- 10442653
- BindingDB
- 85245
- 8356
- ChEBI
- 8249
- ChEMBL
- CHEMBL527
- ZINC
- ZINC000051133897
- Therapeutic Targets Database
- DAP000181
- PharmGKB
- PA450985
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Piroxicam
- FDA label
- Download (74.3 KB)
- MSDS
- Download (73.3 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 Completed Supportive Care Metastatic Cancer 1 somestatus stop reason just information to hide Not Available Unknown Status Prevention Tooth, Nonvital 1 somestatus stop reason just information to hide 4 Completed Supportive Care Cytochrome P450 CYP2C9 Enzyme Deficiency / Impacted Third Molar Tooth / Other Surgical Procedures / Pain 1 somestatus stop reason just information to hide 4 Completed Supportive Care Symptomatic Irreversible Pulpitis (SIP) 1 somestatus stop reason just information to hide 4 Completed Treatment Hypertension 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Akorn inc
- Pfizer laboratories div pfizer inc
- Egis pharmaceuticals
- Genpharm pharmaceuticals inc
- Ivax pharmaceuticals inc sub teva pharmaceuticals usa
- Mutual pharmaceutical co inc
- Mylan pharmaceuticals inc
- Nostrum laboratories inc
- Roxane laboratories inc
- Scs pharmaceuticals
- Teva pharmaceuticals usa inc
- Teva pharmaceuticals usa
- Watson laboratories inc
- Packagers
- Advanced Pharmaceutical Services Inc.
- Aidarex Pharmacuticals LLC
- Akorn Inc.
- Amerisource Health Services Corp.
- AQ Pharmaceuticals Inc.
- A-S Medication Solutions LLC
- Bryant Ranch Prepack
- Corepharma LLC
- Direct Dispensing Inc.
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Egis Pharmaceuticals Public Ltd. Co.
- Goldline Laboratories Inc.
- Group Health Cooperative
- H.J. Harkins Co. Inc.
- Innoviant Pharmacy Inc.
- Keltman Pharmaceuticals Inc.
- Lake Erie Medical and Surgical Supply
- Liberty Pharmaceuticals
- Major Pharmaceuticals
- Medisca Inc.
- Mepha Ltd.
- Murfreesboro Pharmaceutical Nursing Supply
- Mylan
- Nostrum Laboratories Inc.
- Novopharm Ltd.
- Nucare Pharmaceuticals Inc.
- Pack Pharmaceuticals
- Palmetto Pharmaceuticals Inc.
- PD-Rx Pharmaceuticals Inc.
- Pfizer Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Pharmedix
- Physicians Total Care Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Prepak Systems Inc.
- Prescription Dispensing Service Inc.
- Qualitest
- Ranbaxy Laboratories
- Rebel Distributors Corp.
- Redpharm Drug
- Remedy Repack
- Sandhills Packaging Inc.
- Southwood Pharmaceuticals
- St Mary's Medical Park Pharmacy
- Teva Pharmaceutical Industries Ltd.
- UDL Laboratories
- United Research Laboratories Inc.
- Va Cmop Dallas
- Dosage Forms
Form Route Strength Tablet, coated Oral 10 mg Granule, for solution Oral Tablet, effervescent Gel Topical 0.500 g Solution Parenteral 20 mg Tablet Oral 2 g Tablet Oral Aerosol, foam Topical 10 MG/G Cream Topical 10 mg/g Ointment Topical 0.5 % Ointment Topical 10 mg/g Granule, for solution Oral 20 MG Tablet, effervescent 20 MG Tablet, effervescent Oral 20 MG Injection, powder, for solution Intramuscular Injection, powder, for solution Intramuscular 20 MG/2ML Capsule, coated Oral 10 mg Tablet, coated Oral 500 mg Gel Topical 1 % Tablet Oral 20.000 mg Patch Topical Solution Parenteral 21 mg Gel 5 MG Capsule Oral 10.000 mg Gel Cutaneous 0.500 g Solution Intramuscular 20.000 mg Gel Topical Capsule Oral Injection, solution Intramuscular Tablet, for suspension Oral 20 mg Tablet, orally disintegrating Oral 20 mg Capsule Oral 20.000 mg Injection, solution Intramuscular 20 MG/1ML Tablet Oral 20 mg Solution Intramuscular 20 mg Suppository Rectal 10 mg / sup Suppository Rectal 20 mg / sup Gel 5 MG/G Cream Topical Aerosol, foam Topical Gel Topical 0.5 % Tablet, soluble Oral 20 MG Capsule Oral 10 MG Gel Topical 500 mg Cream Topical 1 % Suppository Rectal 20 MG Capsule, coated Oral 20 mg Solution Parenteral 200000 mg Solution / drops Ophthalmic Capsule Oral 10 mg/1 Capsule Oral 20 mg/1 Capsule; tablet Oral 10 MG Gel Topical 0.5 g Injection Intramuscular 20 mg Injection Intramuscular 40 mg Solution Parenteral 40 mg Solution Intramuscular 40 mg Gel Topical 5 mg/g Capsule, coated Oral 20.4 mg Injection, solution Intramuscular; Parenteral 20 MG/ML Injection, solution Intramuscular; Parenteral 20 MG/1ML Tablet, soluble Oral Suppository Rectal 10 mg Tablet Oral 10 mg / cap Capsule, liquid filled Oral 10 mg Gel Topical 1 g Capsule, liquid filled Oral 20 mg Capsule Oral 10 mg / cap Capsule Oral 20 mg / cap Suppository Rectal Injection Intramuscular 20 mg/ml Gel Topical 500 mg/100g Gel Topical 5 MG Injection, solution Powder, for solution Oral 20 mg Kit Oral Capsule, coated Oral 2000000 mg Liquid Ophthalmic 5 mg/1ml Tablet, coated Oral 20 mg Gel Topical 0.5 %w/w Tablet Oral 10 mg Capsule Oral 20 mg Tablet, film coated 10 mg - Prices
Unit description Cost Unit Piroxicam powder 13.16USD g Akten 3.5% drops 7.5USD ml Feldene 20 mg capsule 4.93USD capsule Feldene 10 mg capsule 2.82USD capsule Piroxicam 20 mg capsule 2.69USD capsule Pms-Piroxicam 20 mg Suppository 1.82USD suppository Piroxicam 10 mg capsule 1.44USD capsule Apo-Piroxicam 20 mg Capsule 0.75USD capsule Novo-Pirocam 20 mg Capsule 0.75USD capsule Nu-Pirox 20 mg Capsule 0.75USD capsule Apo-Piroxicam 10 mg Capsule 0.43USD capsule Gen-Piroxicam 10 mg Capsule 0.43USD capsule Novo-Pirocam 10 mg Capsule 0.43USD capsule Nu-Pirox 10 mg Capsule 0.43USD capsule 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 melting point (°C) 198-200 °C PhysProp water solubility 23 mg/L (at 22 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 3.06 AVDEEF,A (1997) logS -4.16 ADME Research, USCD Caco2 permeability -4.45 ADME Research, USCD pKa 6.3 SANGSTER (1994) - Predicted Properties
Property Value Source Water Solubility 0.143 mg/mL ALOGPS logP 2.2 ALOGPS logP 0.6 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 4.76 Chemaxon pKa (Strongest Basic) 3.79 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 99.6 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 87.04 m3·mol-1 Chemaxon Polarizability 32.27 Å3 Chemaxon Number of Rings 3 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 + 0.9898 Blood Brain Barrier - 0.9659 Caco-2 permeable + 0.8867 P-glycoprotein substrate Substrate 0.5786 P-glycoprotein inhibitor I Non-inhibitor 0.7285 P-glycoprotein inhibitor II Non-inhibitor 0.7453 Renal organic cation transporter Non-inhibitor 0.9437 CYP450 2C9 substrate Substrate 0.6437 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Non-substrate 0.7356 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Inhibitor 0.9086 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8789 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8709 Ames test Non AMES toxic 0.8767 Carcinogenicity Non-carcinogens 0.7612 Biodegradation Not ready biodegradable 0.923 Rat acute toxicity 3.1545 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9589 hERG inhibition (predictor II) Non-inhibitor 0.8311
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 177.7012979 predictedDarkChem Lite v0.1.0 [M-H]- 178.3851979 predictedDarkChem Lite v0.1.0 [M-H]- 166.28563 predictedDeepCCS 1.0 (2019) [M+H]+ 177.6479979 predictedDarkChem Lite v0.1.0 [M+H]+ 178.5391979 predictedDarkChem Lite v0.1.0 [M+H]+ 168.64363 predictedDeepCCS 1.0 (2019) [M+Na]+ 177.8416979 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.5877979 predictedDarkChem Lite v0.1.0 [M+Na]+ 174.73677 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Dual cyclooxygenase and peroxidase in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response (PubMed:11939906, PubMed:16373578, PubMed:19540099, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes (PubMed:16373578, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:16373578, PubMed:22942274, PubMed:26859324, PubMed:27226593, PubMed:7592599, PubMed:7947975, PubMed:9261177). Similarly catalyzes successive cyclooxygenation and peroxidation of dihomo-gamma-linoleate (DGLA, C20:3(n-6)) and eicosapentaenoate (EPA, C20:5(n-3)) to corresponding PGH1 and PGH3, the precursors of 1- and 3-series prostaglandins (PubMed:11939906, PubMed:19540099). In an alternative pathway of prostanoid biosynthesis, converts 2-arachidonoyl lysophopholipids to prostanoid lysophopholipids, which are then hydrolyzed by intracellular phospholipases to release free prostanoids (PubMed:27642067). Metabolizes 2-arachidonoyl glycerol yielding the glyceryl ester of PGH2, a process that can contribute to pain response (PubMed:22942274). Generates lipid mediators from n-3 and n-6 polyunsaturated fatty acids (PUFAs) via a lipoxygenase-type mechanism. Oxygenates PUFAs to hydroperoxy compounds and then reduces them to corresponding alcohols (PubMed:11034610, PubMed:11192938, PubMed:9048568, PubMed:9261177). Plays a role in the generation of resolution phase interaction products (resolvins) during both sterile and infectious inflammation (PubMed:12391014). Metabolizes docosahexaenoate (DHA, C22:6(n-3)) to 17R-HDHA, a precursor of the D-series resolvins (RvDs) (PubMed:12391014). As a component of the biosynthetic pathway of E-series resolvins (RvEs), converts eicosapentaenoate (EPA, C20:5(n-3)) primarily to 18S-HEPE that is further metabolized by ALOX5 and LTA4H to generate 18S-RvE1 and 18S-RvE2 (PubMed:21206090). In vascular endothelial cells, converts docosapentaenoate (DPA, C22:5(n-3)) to 13R-HDPA, a precursor for 13-series resolvins (RvTs) shown to activate macrophage phagocytosis during bacterial infection (PubMed:26236990). In activated leukocytes, contributes to oxygenation of hydroxyeicosatetraenoates (HETE) to diHETES (5,15-diHETE and 5,11-diHETE) (PubMed:22068350, PubMed:26282205). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity). During neuroinflammation, plays a role in neuronal secretion of specialized preresolving mediators (SPMs) 15R-lipoxin A4 that regulates phagocytic microglia (By similarity)
- Specific Function
- Enzyme binding
- Gene Name
- PTGS2
- Uniprot ID
- P35354
- Uniprot Name
- Prostaglandin G/H synthase 2
- Molecular Weight
- 68995.625 Da
References
- Blanco FJ, Guitian R, Moreno J, de Toro FJ, Galdo F: Effect of antiinflammatory drugs on COX-1 and COX-2 activity in human articular chondrocytes. J Rheumatol. 1999 Jun;26(6):1366-73. [Article]
- Bugajski J, Glod R, Gadek-Michalska A, Bugajski AJ: Involvement of constitutive (COX-1) and inducible cyclooxygenase (COX-2) in the adrenergic-induced ACTH and corticosterone secretion. J Physiol Pharmacol. 2001 Dec;52(4 Pt 2):795-809. [Article]
- Fackovcova D, Kristova V, Kriska M: Renal damage induced by the treatment with non-opioid analgesics--theoretical assumption or clinical significance. Bratisl Lek Listy. 2000;101(8):417-22. [Article]
- Raju J, Bird RP: Differential modulation of transforming growth factor-betas and cyclooxygenases in the platelet lysates of male F344 rats by dietary lipids and piroxicam. Mol Cell Biochem. 2002 Feb;231(1-2):139-46. [Article]
- Veiga AP, Duarte ID, Avila MN, da Motta PG, Tatsuo MA, Francischi JN: Prevention by celecoxib of secondary hyperalgesia induced by formalin in rats. Life Sci. 2004 Oct 22;75(23):2807-17. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Dual cyclooxygenase and peroxidase that plays an important role in the biosynthesis pathway of prostanoids, a class of C20 oxylipins mainly derived from arachidonate ((5Z,8Z,11Z,14Z)-eicosatetraenoate, AA, C20:4(n-6)), with a particular role in the inflammatory response. The cyclooxygenase activity oxygenates AA to the hydroperoxy endoperoxide prostaglandin G2 (PGG2), and the peroxidase activity reduces PGG2 to the hydroxy endoperoxide prostaglandin H2 (PGH2), the precursor of all 2-series prostaglandins and thromboxanes. This complex transformation is initiated by abstraction of hydrogen at carbon 13 (with S-stereochemistry), followed by insertion of molecular O2 to form the endoperoxide bridge between carbon 9 and 11 that defines prostaglandins. The insertion of a second molecule of O2 (bis-oxygenase activity) yields a hydroperoxy group in PGG2 that is then reduced to PGH2 by two electrons (PubMed:7947975). Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the generation of thromboxane A2 (TXA2), which promotes platelet activation and aggregation, vasoconstriction and proliferation of vascular smooth muscle cells (Probable). Can also use linoleate (LA, (9Z,12Z)-octadecadienoate, C18:2(n-6)) as substrate and produce hydroxyoctadecadienoates (HODEs) in a regio- and stereospecific manner, being (9R)-HODE ((9R)-hydroxy-(10E,12Z)-octadecadienoate) and (13S)-HODE ((13S)-hydroxy-(9Z,11E)-octadecadienoate) its major products (By similarity)
- Specific Function
- Heme binding
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- Blanco FJ, Guitian R, Moreno J, de Toro FJ, Galdo F: Effect of antiinflammatory drugs on COX-1 and COX-2 activity in human articular chondrocytes. J Rheumatol. 1999 Jun;26(6):1366-73. [Article]
- Bugajski J, Glod R, Gadek-Michalska A, Bugajski AJ: Involvement of constitutive (COX-1) and inducible cyclooxygenase (COX-2) in the adrenergic-induced ACTH and corticosterone secretion. J Physiol Pharmacol. 2001 Dec;52(4 Pt 2):795-809. [Article]
- Fackovcova D, Kristova V, Kriska M: Renal damage induced by the treatment with non-opioid analgesics--theoretical assumption or clinical significance. Bratisl Lek Listy. 2000;101(8):417-22. [Article]
- Raju J, Bird RP: Differential modulation of transforming growth factor-betas and cyclooxygenases in the platelet lysates of male F344 rats by dietary lipids and piroxicam. Mol Cell Biochem. 2002 Feb;231(1-2):139-46. [Article]
- Veiga AP, Duarte ID, Avila MN, da Motta PG, Tatsuo MA, Francischi JN: Prevention by celecoxib of secondary hyperalgesia induced by formalin in rats. Life Sci. 2004 Oct 22;75(23):2807-17. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:11093772, PubMed:14559847, PubMed:15766564, PubMed:19965576, PubMed:7574697). Primarily catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) with a preference for the last double bond (PubMed:15766564, PubMed:19965576, PubMed:7574697). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes all trans-retinoic acid toward its 4-hydroxylated form (PubMed:11093772). Displays 16-alpha hydroxylase activity toward estrogen steroid hormones, 17beta-estradiol (E2) and estrone (E1) (PubMed:14559847). Plays a role in the oxidative metabolism of xenobiotics. It is the principal enzyme responsible for the metabolism of the anti-cancer drug paclitaxel (taxol) (PubMed:26427316)
- Specific Function
- Arachidonic acid epoxygenase activity
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Calvo AM, Zupelari-Goncalves P, Dionisio TJ, Brozoski DT, Faria FA, Santos CF: Efficacy of piroxicam for postoperative pain after lower third molar surgery associated with CYP2C8*3 and CYP2C9. J Pain Res. 2017 Jul 6;10:1581-1589. doi: 10.2147/JPR.S138147. eCollection 2017. [Article]
- Kim KA, Oh SO, Park PW, Park JY: Effect of probenecid on the pharmacokinetics of carbamazepine in healthy subjects. Eur J Clin Pharmacol. 2005 Jun;61(4):275-80. doi: 10.1007/s00228-005-0940-7. Epub 2005 May 25. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and steroids (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase) (PubMed:12865317, PubMed:15766564, PubMed:19965576, PubMed:21576599, PubMed:7574697, PubMed:9435160, PubMed:9866708). Catalyzes the epoxidation of double bonds of polyunsaturated fatty acids (PUFA) (PubMed:15766564, PubMed:19965576, PubMed:7574697, PubMed:9866708). Catalyzes the hydroxylation of carbon-hydrogen bonds. Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). Exhibits low catalytic activity for the formation of catechol estrogens from 17beta-estradiol (E2) and estrone (E1), namely 2-hydroxy E1 and E2 (PubMed:12865317). Catalyzes bisallylic hydroxylation and hydroxylation with double-bond migration of polyunsaturated fatty acids (PUFA) (PubMed:9435160, PubMed:9866708). Also metabolizes plant monoterpenes such as limonene. Oxygenates (R)- and (S)-limonene to produce carveol and perillyl alcohol (PubMed:11950794). Contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan (PubMed:25994031)
- Specific Function
- (r)-limonene 6-monooxygenase activity
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Pelkonen O, Maenpaa J, Taavitsainen P, Rautio A, Raunio H: Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica. 1998 Dec;28(12):1203-53. [Article]
- Du H, Wei Z, Yan Y, Xiong Y, Zhang X, Shen L, Ruan Y, Wu X, Xu Q, He L, Qin S: Functional Characterization of Human CYP2C9 Allelic Variants in COS-7 Cells. Front Pharmacol. 2016 Apr 25;7:98. doi: 10.3389/fphar.2016.00098. eCollection 2016. [Article]
- Flockhart Table of Drug Interactions [Link]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Bertucci C, Wainer IW: Improved chromatographic performance of a modified human albumin based stationary phase. Chirality. 1997;9(4):335-40. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Mulato AS, Ho ES, Cihlar T: Nonsteroidal anti-inflammatory drugs efficiently reduce the transport and cytotoxicity of adefovir mediated by the human renal organic anion transporter 1. J Pharmacol Exp Ther. 2000 Oct;295(1):10-5. [Article]
- Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [Article]
- Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [Article]
- Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [Article]
- Tsuda M, Sekine T, Takeda M, Cha SH, Kanai Y, Kimura M, Endou H: Transport of ochratoxin A by renal multispecific organic anion transporter 1. J Pharmacol Exp Ther. 1999 Jun;289(3):1301-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [Article]
- Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [Article]
- Kusuhara H, Sekine T, Utsunomiya-Tate N, Tsuda M, Kojima R, Cha SH, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. J Biol Chem. 1999 May 7;274(19):13675-80. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Antiporter that mediates the transport of conjugated steroids and other specific organic anions at the basal membrane of syncytiotrophoblast and at the apical membrane of proximal tubule epithelial cells, in exchange for anionic compounds (PubMed:10660625, PubMed:11907186, PubMed:15037815, PubMed:15102942, PubMed:15291761, PubMed:15576633, PubMed:17229912, PubMed:18501590, PubMed:26277985, PubMed:28027879). May be responsible for placental absorption of fetal-derived steroid sulfates such as estrone sulfate (E1S) and the steroid hormone precursor dehydroepiandrosterone sulfate (DHEA-S), as well as clearing waste products and xenobiotics from the fetus (PubMed:12409283). Maybe also be involved in placental urate homeostasis (PubMed:17229912). Facilitates the renal reabsorption of organic anions such as urate and derived steroid sulfates (PubMed:15037815, PubMed:17229912). Organic anion glutarate acts as conteranion for E1S renal uptake (PubMed:15037815, PubMed:17229912). Possible transport mode may also include DHEA-S/E1S exchange (PubMed:28027879). Also interacts with inorganic anions such as chloride and hydroxyl ions, therefore possible transport modes may include E1S/Cl(-), E1S/OH(-), urate/Cl(-) and urate/OH(-) (PubMed:17229912). Also mediates the transport of prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) and may be involved in their renal excretion (PubMed:11907186). Also able to uptake anionic drugs, diuretics, bile salts and ochratoxin A (PubMed:10660625, PubMed:26277985). Mediates the unidirectional efflux of glutamate and aspartate (PubMed:28027879). Glutamate efflux down its transmembrane gradient may drive SLC22A11/OAT4-mediated placental uptake of E1S (PubMed:26277985)
- Specific Function
- Organic anion transmembrane transporter activity
- Gene Name
- SLC22A11
- Uniprot ID
- Q9NSA0
- Uniprot Name
- Solute carrier family 22 member 11
- Molecular Weight
- 59970.945 Da
References
- Babu E, Takeda M, Narikawa S, Kobayashi Y, Enomoto A, Tojo A, Cha SH, Sekine T, Sakthisekaran D, Endou H: Role of human organic anion transporter 4 in the transport of ochratoxin A. Biochim Biophys Acta. 2002 Jun 12;1590(1-3):64-75. [Article]
- Takeda M, Khamdang S, Narikawa S, Kimura H, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of methotrexate transport and its drug interactions with human organic anion transporters. J Pharmacol Exp Ther. 2002 Aug;302(2):666-71. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Mediates the Na(+)-independent transport of steroid sulfate conjugates and other specific organic anions (PubMed:10873595, PubMed:11159893, PubMed:11932330, PubMed:12724351, PubMed:14610227, PubMed:16908597, PubMed:18501590, PubMed:20507927, PubMed:22201122, PubMed:23531488, PubMed:25132355, PubMed:26383540, PubMed:27576593, PubMed:28408210, PubMed:29871943, PubMed:34628357). Responsible for the transport of estrone 3-sulfate (E1S) through the basal membrane of syncytiotrophoblast, highlighting a potential role in the placental absorption of fetal-derived sulfated steroids including the steroid hormone precursor dehydroepiandrosterone sulfate (DHEA-S) (PubMed:11932330, PubMed:12409283). Also facilitates the uptake of sulfated steroids at the basal/sinusoidal membrane of hepatocytes, therefore accounting for the major part of organic anions clearance of liver (PubMed:11159893). Mediates the intestinal uptake of sulfated steroids (PubMed:12724351, PubMed:28408210). Mediates the uptake of the neurosteroids DHEA-S and pregnenolone sulfate (PregS) into the endothelial cells of the blood-brain barrier as the first step to enter the brain (PubMed:16908597, PubMed:25132355). Also plays a role in the reuptake of neuropeptides such as substance P/TAC1 and vasoactive intestinal peptide/VIP released from retinal neurons (PubMed:25132355). May act as a heme transporter that promotes cellular iron availability via heme oxygenase/HMOX2 and independently of TFRC (PubMed:35714613). Also transports heme by-product coproporphyrin III (CPIII), and may be involved in their hepatic disposition (PubMed:26383540). Mediates the uptake of other substrates such as prostaglandins D2 (PGD2), E1 (PGE1) and E2 (PGE2), taurocholate, L-thyroxine, leukotriene C4 and thromboxane B2 (PubMed:10873595, PubMed:14610227, PubMed:19129463, PubMed:29871943, Ref.25). May contribute to regulate the transport of organic compounds in testis across the blood-testis-barrier (Probable). Shows a pH-sensitive substrate specificity which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:14610227, PubMed:19129463, PubMed:22201122). The exact transport mechanism has not been yet deciphered but most likely involves an anion exchange, coupling the cellular uptake of organic substrate with the efflux of an anionic compound (PubMed:19129463, PubMed:20507927, PubMed:26277985). Hydrogencarbonate/HCO3(-) acts as a probable counteranion that exchanges for organic anions (PubMed:19129463). Cytoplasmic glutamate may also act as counteranion in the placenta (PubMed:26277985). An inwardly directed proton gradient has also been proposed as the driving force of E1S uptake with a (H(+):E1S) stoichiometry of (1:1) (PubMed:20507927)
- Specific Function
- Bile acid transmembrane transporter activity
- Gene Name
- SLCO2B1
- Uniprot ID
- O94956
- Uniprot Name
- Solute carrier organic anion transporter family member 2B1
- Molecular Weight
- 76697.93 Da
References
- Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [Article]
Drug created at June 13, 2005 13:24 / Updated at September 15, 2024 01:12