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Identification
- Summary
Teriflunomide is a pyrimidine synthesis inhibitor with anti-inflammatory and immunomodulatory properties used to treat patients with the relapsing-remitting form of multiple sclerosis.
- Brand Names
- Aubagio
- Generic Name
- Teriflunomide
- DrugBank Accession Number
- DB08880
- Background
Teriflunomide is the active metabolite of leflunomide, and it acts as an immunomodulatory agent by inhibiting pyrimidine synthesis. It is marketed under the name Aubagio® and is indicated for the treatment of multiple sclerosis, specifically relapsing forms. The FDA label states an important warning about the risk of hepatoxicity and teratogenicity for patients using teriflunomide.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Teriflunomide (DB08880)
- Weight
- Average: 270.2073
Monoisotopic: 270.061612157 - Chemical Formula
- C12H9F3N2O2
- Synonyms
- (Z)-2-cyano-alpha,alpha,alpha-trifluoro-3-hydroxy-p-crotonotoluidide
- Teriflunomida
- Tériflunomide
- Teriflunomide
- Teriflunomidum
- External IDs
- A 77-1726
- A 771726
- A-771726
- A77 1726
- A771726
- HMR 1726
- HMR-1726
- HMR1726
Pharmacology
- Indication
Used in the treatment of relapsing forms of multiple sclerosis (MS).
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Multiple sclerosis •••••••••••• - Contraindications & Blackbox Warnings
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Teriflunomide is an immunomodulatory agent that decreases the amount of activated CNS lymphocytes, which results in anti-inflammatory and antiproliferative effects.
- Mechanism of action
The exact mechanism by which teriflunomide acts in MS is not known. What is known is that teriflunomide prevents pyrimidine synthesis by inhibiting the mitochondrial enzyme dihydroorotate dehydrogenase, and this may be involved in its immunomodulatory effect in MS.
Target Actions Organism ADihydroorotate dehydrogenase (quinone), mitochondrial inhibitorPlasmodium falciparum (isolate 3D7) A3-hydroxy-3-methylglutaryl-coenzyme A reductase inhibitorHumans UDihydroorotate dehydrogenase (quinone), mitochondrial inhibitorHumans - Absorption
After oral administration of teriflunomide, maximum plasma concentrations are reached, on average, in 1-4 hours.
- Volume of distribution
After a single intravenous dose, the volume of distribution is 11 L.
- Protein binding
Teriflunomide is extensively plasma protein bound(>99%).
- Metabolism
Teriflunomide mainly undergoes hydrolyis to minor metabolites. Other minor metabolic pathways include oxidation, N-acetylation and sulfate conjugation. Teriflunomide is not metabolized by CYP450 or flavin monoamine oxidase.
- Route of elimination
Teriflunomide is eliminated unchanged and mainly through bile. Specifically 37.5% is eliminated in the feces and 22.6% in urine.
- Half-life
The median half-life is 18 to 19 days.
- Clearance
After a single IV dose, teriflunomide has a total body clearance of 30.5 mL/h.
- 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
Teriflunomide is contraindicated in pregnant women or women of childbearing age due to the risk of teratogenicity. Teriflunomide is also contraindicated in severe hepatic impairment due to reports of hepatotoxicity, hepatic failure, and death.
- 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 softwareAbatacept The risk or severity of adverse effects can be increased when Abatacept is combined with Teriflunomide. Abemaciclib Teriflunomide may decrease the excretion rate of Abemaciclib which could result in a higher serum level. Acenocoumarol The therapeutic efficacy of Acenocoumarol can be decreased when used in combination with Teriflunomide. Acetaminophen The serum concentration of Acetaminophen can be decreased when it is combined with Teriflunomide. Acitretin The risk or severity of liver damage can be increased when Acitretin is combined with Teriflunomide. - Food Interactions
- Take with or without 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.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Aubagio Tablet, film coated 7 mg Oral SANOFI WINTHROP INDUSTRIE 2022-05-04 Not applicable EU 
Aubagio Tablet, film coated 14 mg Oral SANOFI WINTHROP INDUSTRIE 2016-09-08 Not applicable EU Aubagio Tablet, film coated 7 mg/1 Oral Genzyme Corporation 2013-05-01 Not applicable US 
Aubagio Tablet, film coated 14 mg Oral SANOFI WINTHROP INDUSTRIE 2016-09-08 Not applicable EU Aubagio Tablet, film coated 14 mg Oral SANOFI WINTHROP INDUSTRIE 2016-09-08 Not applicable EU - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ach-teriflunomide Tablet 14 mg Oral Accord Healthcare, S.L.U. 2022-05-19 Not applicable Canada 
Apo-teriflunomide Tablet 14 mg Oral Apotex Corporation 2022-05-16 Not applicable Canada Auro-teriflunomide Tablet 14 mg Oral Auro Pharma Inc Not applicable Not applicable Canada Jamp Teriflunomide Tablet 14 mg Oral Jamp Pharma Corporation 2022-05-16 Not applicable Canada Mar-teriflunomide Tablet 14 mg Oral Marcan Pharmaceuticals Inc 2022-05-18 Not applicable Canada
Categories
- ATC Codes
- L04AK02 — Teriflunomide
- Drug Categories
- Acids, Acyclic
- Amines
- Analgesics
- Analgesics, Non-Narcotic
- Aniline Compounds
- Anti-Inflammatory Agents
- Antineoplastic and Immunomodulating Agents
- Antirheumatic Agents
- BCRP/ABCG2 Inhibitors
- BCRP/ABCG2 Substrates
- Benzene Derivatives
- Butyrates
- Cytochrome P-450 CYP1A2 Inducers
- Cytochrome P-450 CYP1A2 Inducers (strength unknown)
- Cytochrome P-450 CYP1A2 Inducers (weak)
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (moderate)
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Dihydroorotate dehydrogenase (DHODH) inhibitors
- Dihydroorotate Dehydrogenase Inhibitors
- Fatty Acids
- Fatty Acids, Volatile
- Hepatotoxic Agents
- Hydroxy Acids
- Immunologic Factors
- Immunomodulatory Agents
- Immunosuppressive Agents
- Lipids
- OAT3/SLC22A8 Inhibitors
- OATP1B1/SLCO1B1 Inhibitors
- Peripheral Nervous System Agents
- Pyrimidine Synthesis Inhibitor
- Selective Immunosuppressants
- Sensory System Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as trifluoromethylbenzenes. These are organofluorine compounds that contain a benzene ring substituted with one or more trifluoromethyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Trifluoromethylbenzenes
- Direct Parent
- Trifluoromethylbenzenes
- Alternative Parents
- Anilides / N-arylamides / Vinylogous acids / Secondary carboxylic acid amides / Nitriles / Enols / Organopnictogen compounds / Organofluorides / Organic oxides / Hydrocarbon derivatives show 2 more
- Substituents
- Alkyl fluoride / Alkyl halide / Anilide / Aromatic homomonocyclic compound / Carbonitrile / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Enol / Hydrocarbon derivative show 13 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- nitrile, enamide, aromatic amide, enol, (trifluoromethyl)benzenes (CHEBI:68540)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 1C058IKG3B
- CAS number
- 163451-81-8
- InChI Key
- UTNUDOFZCWSZMS-YFHOEESVSA-N
- InChI
- InChI=1S/C12H9F3N2O2/c1-7(18)10(6-16)11(19)17-9-4-2-8(3-5-9)12(13,14)15/h2-5,18H,1H3,(H,17,19)/b10-7-
- IUPAC Name
- (2Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide
- SMILES
- C\C(O)=C(/C#N)C(=O)NC1=CC=C(C=C1)C(F)(F)F
References
- Synthesis Reference
Keshav Deo, Samir Patel, Snehal Dhol, Sunil Sanghani, Vishal Ray, " PROCESS FOR PREPARING TERIFLUNOMIDE." U.S. Patent US20110092727, issued April 21, 2011.
US20110092727- General References
- O'Connor PW, Li D, Freedman MS, Bar-Or A, Rice GP, Confavreux C, Paty DW, Stewart JA, Scheyer R: A Phase II study of the safety and efficacy of teriflunomide in multiple sclerosis with relapses. Neurology. 2006 Mar 28;66(6):894-900. [Article]
- Tallantyre E, Evangelou N, Constantinescu CS: Spotlight on teriflunomide. Int MS J. 2008 Jun;15(2):62-8. [Article]
- FDA Approved Drug Products: AUBAGIO (teriflunomide) tablets [Link]
- External Links
- KEGG Drug
- D10172
- PubChem Compound
- 54684141
- PubChem Substance
- 347827807
- ChemSpider
- 16737143
- BindingDB
- 50018011
- 1310520
- ChEBI
- 68540
- ChEMBL
- CHEMBL973
- ZINC
- ZINC000013512456
- PDBe Ligand
- A26
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Teriflunomide
- PDB Entries
- 1d3h / 1tv5
- FDA label
- Download (527 KB)
- MSDS
- Download (124 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 Not Available Multiple Sclerosis 3 somestatus stop reason just information to hide Not Available Completed Not Available Relapsing Remitting Multiple Sclerosis (RRMS) 3 somestatus stop reason just information to hide Not Available Completed Not Available Tecfidera / Teriflunomide 1 somestatus stop reason just information to hide Not Available Enrolling by Invitation Not Available Adherence, Medication / Multiple Sclerosis 1 somestatus stop reason just information to hide Not Available Unknown Status Treatment Multiple Sclerosis / Relapsing Remitting Multiple Sclerosis (RRMS) / Secondary Progressive Multiple Sclerosis (SPMS) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 14 mg Tablet, film coated Oral 7 MG Tablet, film coated Oral 14 mg Tablet, film coated Oral 14.0 mg Tablet Oral 14.000 mg Tablet Oral 14 mg/1 Tablet Oral 7 mg/1 Tablet, coated Oral 14 mg/1 Tablet, coated Oral 7 mg/1 Tablet, film coated Oral 14 mg/1 Tablet, film coated Oral 7 mg/1 Tablet, coated Oral 14 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6794410 Yes 2004-09-21 2027-03-12 US US9186346 Yes 2015-11-17 2034-08-04 US US8802735 Yes 2014-08-12 2031-03-14 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility Soluble in DMSO (practically insoluble in water). From FDA label. - Predicted Properties
Property Value Source Water Solubility 0.0124 mg/mL ALOGPS logP 2.3 ALOGPS logP 2.14 Chemaxon logS -4.3 ALOGPS pKa (Strongest Acidic) 5.48 Chemaxon pKa (Strongest Basic) -3.2 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 73.12 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 64.39 m3·mol-1 Chemaxon Polarizability 23.15 Å3 Chemaxon Number of Rings 1 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0gvo-7890000000-a02cc8999b41f93431c0 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-9100000000-2a60cc190de61052600c Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-5090000000-234a7b4755738cefe042 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-9000000000-96b31ed1fcc72ae700a5 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-1900000000-f0a06b6314701f5201f4 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00kf-9210000000-0f3745960114418f4083 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-5900000000-c6f7e506c6a2813d650c 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]- 158.53004 predictedDeepCCS 1.0 (2019) [M+H]+ 160.88805 predictedDeepCCS 1.0 (2019) [M+Na]+ 167.66957 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Plasmodium falciparum (isolate 3D7)
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor.
- Specific Function
- dihydroorotate dehydrogenase (quinone) activity
- Gene Name
- Not Available
- Uniprot ID
- Q08210
- Uniprot Name
- Dihydroorotate dehydrogenase (quinone), mitochondrial
- Molecular Weight
- 65557.87 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the conversion of (3S)-hydroxy-3-methylglutaryl-CoA (HMG-CoA) to mevalonic acid, the rate-limiting step in the synthesis of cholesterol and other isoprenoids, thus plays a critical role in cellular cholesterol homeostasis (PubMed:21357570, PubMed:2991281, PubMed:36745799, PubMed:6995544). HMGCR is the main target of statins, a class of cholesterol-lowering drugs (PubMed:11349148, PubMed:18540668, PubMed:36745799)
- Specific Function
- coenzyme A binding
- Gene Name
- HMGCR
- Uniprot ID
- P04035
- Uniprot Name
- 3-hydroxy-3-methylglutaryl-coenzyme A reductase
- Molecular Weight
- 97475.155 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Catalyzes the conversion of dihydroorotate to orotate with quinone as electron acceptor. Required for UMP biosynthesis via de novo pathway
- Specific Function
- dihydroorotase activity
- Gene Name
- DHODH
- Uniprot ID
- Q02127
- Uniprot Name
- Dihydroorotate dehydrogenase (quinone), mitochondrial
- Molecular Weight
- 42866.93 Da
References
- Palmer AM: Teriflunomide, an inhibitor of dihydroorotate dehydrogenase for the potential oral treatment of multiple sclerosis. Curr Opin Investig Drugs. 2010 Nov;11(11):1313-23. [Article]
- Davis JP, Cain GA, Pitts WJ, Magolda RL, Copeland RA: The immunosuppressive metabolite of leflunomide is a potent inhibitor of human dihydroorotate dehydrogenase. Biochemistry. 1996 Jan 30;35(4):1270-3. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids, steroid hormones and vitamins (PubMed:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). 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:10681376, PubMed:11555828, PubMed:12865317, PubMed:19965576, PubMed:9435160). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:11555828, PubMed:12865317). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2 (PubMed:11555828, PubMed:12865317). Metabolizes cholesterol toward 25-hydroxycholesterol, a physiological regulator of cellular cholesterol homeostasis (PubMed:21576599). May act as a major enzyme for all-trans retinoic acid biosynthesis in the liver. Catalyzes two successive oxidative transformation of all-trans retinol to all-trans retinal and then to the active form all-trans retinoic acid (PubMed:10681376). Primarily catalyzes stereoselective epoxidation of the last double bond of polyunsaturated fatty acids (PUFA), displaying a strong preference for the (R,S) stereoisomer (PubMed:19965576). Catalyzes bisallylic hydroxylation and omega-1 hydroxylation of PUFA (PubMed:9435160). May also participate in eicosanoids metabolism by converting hydroperoxide species into oxo metabolites (lipoxygenase-like reaction, NADPH-independent) (PubMed:21068195). Plays a role in the oxidative metabolism of xenobiotics. Catalyzes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin (PubMed:14725854). Metabolizes caffeine via N3-demethylation (Probable)
- Specific Function
- aromatase activity
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58406.915 Da
References
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Broad substrate specificity ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes a wide variety of physiological compounds, dietary toxins and xenobiotics from cells (PubMed:11306452, PubMed:12958161, PubMed:19506252, PubMed:20705604, PubMed:28554189, PubMed:30405239, PubMed:31003562). Involved in porphyrin homeostasis, mediating the export of protoporphyrin IX (PPIX) from both mitochondria to cytosol and cytosol to extracellular space, it also functions in the cellular export of heme (PubMed:20705604, PubMed:23189181). Also mediates the efflux of sphingosine-1-P from cells (PubMed:20110355). Acts as a urate exporter functioning in both renal and extrarenal urate excretion (PubMed:19506252, PubMed:20368174, PubMed:22132962, PubMed:31003562, PubMed:36749388). In kidney, it also functions as a physiological exporter of the uremic toxin indoxyl sulfate (By similarity). Also involved in the excretion of steroids like estrone 3-sulfate/E1S, 3beta-sulfooxy-androst-5-en-17-one/DHEAS, and other sulfate conjugates (PubMed:12682043, PubMed:28554189, PubMed:30405239). Mediates the secretion of the riboflavin and biotin vitamins into milk (By similarity). Extrudes pheophorbide a, a phototoxic porphyrin catabolite of chlorophyll, reducing its bioavailability (By similarity). Plays an important role in the exclusion of xenobiotics from the brain (Probable). It confers to cells a resistance to multiple drugs and other xenobiotics including mitoxantrone, pheophorbide, camptothecin, methotrexate, azidothymidine, and the anthracyclines daunorubicin and doxorubicin, through the control of their efflux (PubMed:11306452, PubMed:12477054, PubMed:15670731, PubMed:18056989, PubMed:31254042). In placenta, it limits the penetration of drugs from the maternal plasma into the fetus (By similarity). May play a role in early stem cell self-renewal by blocking differentiation (By similarity)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- Broad substrate specificity ATP-binding cassette transporter ABCG2
- Molecular Weight
- 72313.47 Da
References
- Kis E, Nagy T, Jani M, Molnar E, Janossy J, Ujhellyi O, Nemet K, Heredi-Szabo K, Krajcsi P: Leflunomide and its metabolite A771726 are high affinity substrates of BCRP: implications for drug resistance. Ann Rheum Dis. 2009 Jul;68(7):1201-7. doi: 10.1136/ard.2007.086264. Epub 2008 Apr 8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Mediates the Na(+)-independent uptake of organic anions (PubMed:10358072, PubMed:15159445, PubMed:17412826). Shows broad substrate specificity, can transport both organic anions such as bile acid taurocholate (cholyltaurine) and conjugated steroids (dehydroepiandrosterone 3-sulfate, 17-beta-glucuronosyl estradiol, and estrone 3-sulfate), as well as eicosanoids (prostaglandin E2, thromboxane B2, leukotriene C4, and leukotriene E4), and thyroid hormones (T4/L-thyroxine, and T3/3,3',5'-triiodo-L-thyronine) (PubMed:10358072, PubMed:10601278, PubMed:10873595, PubMed:11159893, PubMed:12196548, PubMed:12568656, PubMed:15159445, PubMed:15970799, PubMed:16627748, PubMed:17412826, PubMed:19129463, PubMed:26979622). Can take up bilirubin glucuronides from plasma into the liver, contributing to the detoxification-enhancing liver-blood shuttling loop (PubMed:22232210). Involved in the clearance of endogenous and exogenous substrates from the liver (PubMed:10358072, PubMed:10601278). Transports coproporphyrin I and III, by-products of heme synthesis, and may be involved in their hepatic disposition (PubMed:26383540). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can transport HMG-CoA reductase inhibitors (also known as statins), such as pravastatin and pitavastatin, a clinically important class of hypolipidemic drugs (PubMed:10601278, PubMed:15159445, PubMed:15970799). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drug methotrexate (PubMed:23243220). May also transport antihypertension agents, such as the angiotensin-converting enzyme (ACE) inhibitor prodrug enalapril, and the highly selective angiotensin II AT1-receptor antagonist valsartan, in the liver (PubMed:16624871, PubMed:16627748). Shows a pH-sensitive substrate specificity towards prostaglandin E2 and T4 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:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463)
- Specific Function
- bile acid transmembrane transporter activity
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
Drug created at May 20, 2013 02:55 / Updated at August 26, 2024 19:24