Details
Stereochemistry | ACHIRAL |
Molecular Formula | C12H9F3N2O2 |
Molecular Weight | 270.2073 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
Stereo Comments | Teriflunomide then can interconvert between the E and Z enolic forms (and the corresponding keto-amide), with the Z-enol being the most stable and therefore most predominant form (https://en.wikipedia.org/wiki/Leflunomide) |
SHOW SMILES / InChI
SMILES
C\C(O)=C(/C#N)C(=O)NC1=CC=C(C=C1)C(F)(F)F
InChI
InChIKey=UTNUDOFZCWSZMS-YFHOEESVSA-N
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-
Molecular Formula | C12H9F3N2O2 |
Molecular Weight | 270.2073 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/202992s003lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020905s031lbl.pdfCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/9666414
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/202992s003lbl.pdfhttp://www.accessdata.fda.gov/drugsatfda_docs/label/2016/020905s031lbl.pdf
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/9666414
Leflunomide is a pyrimidine synthesis inhibitor belonging to the DMARD (disease-modifying antirheumatic drug) class of drugs, which are chemically and pharmacologically very heterogeneous. Leflunomide was approved by FDA and in many other countries. Leflunomide is an isoxazole immunomodulatory agent that inhibits dihydroorotate dehydrogenase (a mitochondrial enzyme involved in de novo pyrimidine synthesis) and has antiproliferative activity. Several in vivo and in vitro experimental models have demonstrated an anti-inflammatory effect. Leflunomide is rapidly metabolized to its active form, teriflunomide (A77 1726). Two mechanisms of action have been identified for A77 1726: inhibition of dihydroorotate dehydrogenase (DHODH) and inhibition of tyrosine kinases. DHODH inhibition occurs at lower concentrations of A77 1726 than that of tyrosine kinases and is currently considered the major mode of action. Human dihydroorotate dehydrogenase consists of 2 domains: an α/β-barrel domain containing the active site and an α-helical domain that forms a tunnel leading to the active site. A77 1726 binds to the hydrophobic tunnel at a site near the flavin mononucleotide. Inhibition of dihydroorotate dehydrogenase by A77 1726 prevents production of rUMP by the de novo pathway; such inhibition leads to decreased rUMP levels, decreased DNA and RNA synthesis, inhibition of cell proliferation, and G1 cell cycle arrest. It is through this action that leflunomide inhibits autoimmune T-cell proliferation and production of autoantibodies by B cells. Since salvage pathways are expected to sustain cells arrested in the G1 phase, the activity of leflunomide is cytostatic rather than cytotoxic. Tyrosine kinases activate signalling pathways leading to DNA repair, apoptosis and cell proliferation. Inhibition of tyrosine kinases can help to treating cancer by preventing repair of tumor cells. Teriflunomide is also an inhibitor of CYP2C8 in vivo. In patients taking leflunomide, exposure of drugs metabolized by CYP2C8 (e.g., paclitaxel, pioglitazone, repaglinide, rosiglitazone) may be increased. Teriflunomide inhibits the activity of BCRP and OATP1B1/1B3 in vivo. For a patient taking leflunomide, the dose of rosuvastatin should not exceed 10 mg once daily. For other substrates of BCRP (e.g., mitoxantrone) and drugs in the OATP family (e.g., methotrexate, rifampin), especially HMG-Co reductase inhibitors (e.g., atorvastatin, nateglinide, pravastatin, repaglinide, and simvastatin), consider reducing the dose of these drugs and monitor patients closely for signs and symptoms of increased exposures to the drugs while patients are taking leflunomide.
CNS Activity
Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=18782502https://www.ncbi.nlm.nih.gov/pubmed/?term=23637535
Curator's Comment: Teriflunomide, is the active metabolite of leflunomide, has only limited penetration across the blood–brain barrier
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Q02127 Gene ID: 1723.0 Gene Symbol: DHODH Target Organism: Homo sapiens (Human) |
160.0 nM [Ki] | ||
Target ID: CHEMBL1966 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9666414 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | AUBAGIO Approved UseIndicated for the treatment of patients with relapsing forms of multiple sclerosis. Launch Date1.34740797E12 |
|||
Palliative | ARAVA Approved UseLeflunomide is indicated in adults for the treatment of active rheumatoid arthritis (RA): to reduce signs and symptoms to inhibit structural damage as evidenced by X-ray erosions and joint space narrowing to improve physical function (see CLINICAL STUDIES ). Aspirin, nonsteroidal anti-inflammatory agents and/or low dose corticosteroids may be continued during treatment with leflunomide (see PRECAUTIONS: Drug Interactions: NSAIDs ). The combined use of leflunomide with antimalarials, intramuscular or oral gold, D penicillamine, azathioprine, or methotrexate has not been adequately studied (see WARNINGS: Immunosuppression Potential/Bone Marrow Suppression ). Launch Date9.0538561E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.06 μg/mL |
7 mg single, oral dose: 7 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERIFLUNOMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
100 μg × h/mL |
7 mg single, oral dose: 7 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERIFLUNOMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
243 h |
7 mg single, oral dose: 7 mg route of administration: Oral experiment type: SINGLE co-administered: |
TERIFLUNOMIDE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1% |
TERIFLUNOMIDE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
14 mg 1 times / day multiple, oral Recommended Dose: 14 mg, 1 times / day Route: oral Route: multiple Dose: 14 mg, 1 times / day Sources: Page: p.923 |
unhealthy, 36 n = 250 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 36 Sex: M+F Population Size: 250 Sources: Page: p.923 |
Disc. AE: ALT increased, Hepatic enzyme increased... AEs leading to discontinuation/dose reduction: ALT increased (3.6%) Sources: Page: p.923Hepatic enzyme increased (0.4%) |
14 mg 1 times / day multiple, oral Recommended Dose: 14 mg, 1 times / day Route: oral Route: multiple Dose: 14 mg, 1 times / day Sources: Page: p.8,9 |
unhealthy, 37 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 37 Sex: M+F Sources: Page: p.8,9 |
Disc. AE: ALT increased... AEs leading to discontinuation/dose reduction: ALT increased (2.6%) Sources: Page: p.8,9 |
14 mg 1 times / day multiple, oral Recommended Dose: 14 mg, 1 times / day Route: oral Route: multiple Dose: 14 mg, 1 times / day Sources: Page: p.2781 |
unhealthy, 37.8 ± 9.7 n = 43 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 37.8 ± 9.7 Sex: M+F Population Size: 43 Sources: Page: p.2781 |
Disc. AE: ALT increased, AST increased... AEs leading to discontinuation/dose reduction: ALT increased (4.7%) Sources: Page: p.2781AST increased (4.7%) Neutropenia (4.7%) |
672 mg single, oral Overdose |
unknown |
|
14 mg 1 times / day multiple, oral Recommended Dose: 14 mg, 1 times / day Route: oral Route: multiple Dose: 14 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Multiple sclerosis Sources: Page: p.1 |
Disc. AE: Hepatotoxicity, Liver injury... AEs leading to discontinuation/dose reduction: Hepatotoxicity Sources: Page: p.1Liver injury (severe) Liver failure (grade 5) Disorder fetal |
14 mg 1 times / day multiple, oral Recommended Dose: 14 mg, 1 times / day Route: oral Route: multiple Dose: 14 mg, 1 times / day Sources: Page: p.7 |
unhealthy Health Status: unhealthy Condition: Multiple sclerosis Sources: Page: p.7 |
Disc. AE: Peripheral neuropathy... AEs leading to discontinuation/dose reduction: Peripheral neuropathy (1.9%) Sources: Page: p.7 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hepatic enzyme increased | 0.4% Disc. AE |
14 mg 1 times / day multiple, oral Recommended Dose: 14 mg, 1 times / day Route: oral Route: multiple Dose: 14 mg, 1 times / day Sources: Page: p.923 |
unhealthy, 36 n = 250 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 36 Sex: M+F Population Size: 250 Sources: Page: p.923 |
ALT increased | 3.6% Disc. AE |
14 mg 1 times / day multiple, oral Recommended Dose: 14 mg, 1 times / day Route: oral Route: multiple Dose: 14 mg, 1 times / day Sources: Page: p.923 |
unhealthy, 36 n = 250 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 36 Sex: M+F Population Size: 250 Sources: Page: p.923 |
ALT increased | 2.6% Disc. AE |
14 mg 1 times / day multiple, oral Recommended Dose: 14 mg, 1 times / day Route: oral Route: multiple Dose: 14 mg, 1 times / day Sources: Page: p.8,9 |
unhealthy, 37 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 37 Sex: M+F Sources: Page: p.8,9 |
ALT increased | 4.7% Disc. AE |
14 mg 1 times / day multiple, oral Recommended Dose: 14 mg, 1 times / day Route: oral Route: multiple Dose: 14 mg, 1 times / day Sources: Page: p.2781 |
unhealthy, 37.8 ± 9.7 n = 43 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 37.8 ± 9.7 Sex: M+F Population Size: 43 Sources: Page: p.2781 |
AST increased | 4.7% Disc. AE |
14 mg 1 times / day multiple, oral Recommended Dose: 14 mg, 1 times / day Route: oral Route: multiple Dose: 14 mg, 1 times / day Sources: Page: p.2781 |
unhealthy, 37.8 ± 9.7 n = 43 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 37.8 ± 9.7 Sex: M+F Population Size: 43 Sources: Page: p.2781 |
Neutropenia | 4.7% Disc. AE |
14 mg 1 times / day multiple, oral Recommended Dose: 14 mg, 1 times / day Route: oral Route: multiple Dose: 14 mg, 1 times / day Sources: Page: p.2781 |
unhealthy, 37.8 ± 9.7 n = 43 Health Status: unhealthy Condition: Multiple sclerosis Age Group: 37.8 ± 9.7 Sex: M+F Population Size: 43 Sources: Page: p.2781 |
Disorder fetal | Disc. AE | 14 mg 1 times / day multiple, oral Recommended Dose: 14 mg, 1 times / day Route: oral Route: multiple Dose: 14 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Multiple sclerosis Sources: Page: p.1 |
Hepatotoxicity | Disc. AE | 14 mg 1 times / day multiple, oral Recommended Dose: 14 mg, 1 times / day Route: oral Route: multiple Dose: 14 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Multiple sclerosis Sources: Page: p.1 |
Liver failure | grade 5 Disc. AE |
14 mg 1 times / day multiple, oral Recommended Dose: 14 mg, 1 times / day Route: oral Route: multiple Dose: 14 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Multiple sclerosis Sources: Page: p.1 |
Liver injury | severe Disc. AE |
14 mg 1 times / day multiple, oral Recommended Dose: 14 mg, 1 times / day Route: oral Route: multiple Dose: 14 mg, 1 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Multiple sclerosis Sources: Page: p.1 |
Peripheral neuropathy | 1.9% Disc. AE |
14 mg 1 times / day multiple, oral Recommended Dose: 14 mg, 1 times / day Route: oral Route: multiple Dose: 14 mg, 1 times / day Sources: Page: p.7 |
unhealthy Health Status: unhealthy Condition: Multiple sclerosis Sources: Page: p.7 |
PubMed
Title | Date | PubMed |
---|---|---|
Differential modulation of pro- and anti-inflammatory cytokine receptors by N-(4-trifluoromethylphenyl)-2-cyano-3-hydroxy-crotonic acid amide (A77 1726), the physiologically active metabolite of the novel immunomodulator leflunomide. | 1998 May 1 |
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Leflunomide, a novel immunomodulator for the treatment of active rheumatoid arthritis. | 1999 Nov |
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Leflunomide: mode of action in the treatment of rheumatoid arthritis. | 2000 Nov |
|
Vasculitis occurring during leflunomide therapy. | 2001 |
|
A randomized, controlled, single-blind trial of leflunomide in the treatment of rheumatoid arthritis. | 2001 |
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Benefits of leflunomide in systemic lupus erythematosus: a pilot observational study. | 2001 |
|
What's new in rheumatoid arthritis? An evidenced based review. | 2001 Apr |
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Leflunomide: new antirheumatic drug. Effect on pregnancy outcomes. | 2001 Apr |
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A multi-institutional phase ii study of SU101, a platelet-derived growth factor receptor inhibitor, for patients with hormone-refractory prostate cancer. | 2001 Apr |
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Rational use of new and existing disease-modifying agents in rheumatoid arthritis. | 2001 Apr 17 |
|
Diabetic rats transplanted with adult porcine islets and immunosuppressed with cyclosporine A, mycophenolate mofetil, and leflunomide remain normoglycemic for up to 100 days. | 2001 Apr 27 |
|
The Saccharomyces cerevisiae MLF6/YPL244C gene, which encodes a possible yeast homologue of mammalian UDP-galactose transporter, confers resistance to the immunosuppressive drug, leflunomide. | 2001 Aug |
|
Progress in the treatment of rheumatoid arthritis. | 2001 Dec 12 |
|
Acetyl-coa: alcohol acetyltransferase activity and aroma formation in ripening melon fruits. | 2001 Feb |
|
Teratogen update: reproductive risks of leflunomide (Arava); a pyrimidine synthesis inhibitor: counseling women taking leflunomide before or during pregnancy and men taking leflunomide who are contemplating fathering a child. | 2001 Feb |
|
Radiography of rheumatoid arthritis in the time of increasing drug effectiveness. | 2001 Feb |
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Current management of rheumatoid arthritis. | 2001 Feb 15 |
|
Combination of antilymphocyte globulin and leflunomide leads to superior grafts. | 2001 Feb-Mar |
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Leflunomide analog, MNA-715, plus cyclosporine reduces renal allograft rejection in mismatched dogs. | 2001 Feb-Mar |
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Newer immunomodulating drugs in rheumatoid arthritis may precipitate glomerulonephritis. | 2001 Jan |
|
Inhibition of herpes simplex virus type 1 by the experimental immunosuppressive agent leflunomide. | 2001 Jan 15 |
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Discussion. Treatment algorithm: managing rheumatoid arthritis. | 2001 Jul |
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Flow cytometric quantitation of calcium-dependent and -independent mitogen-stimulation of T cell functions in whole blood: inhibition by immunosuppressive drugs in vitro. | 2001 Jul 1 |
|
Treatment of immune-mediated skin diseases: future perspectives. | 2001 Jul-Aug |
|
Conventional DMARD options for patients with a suboptimal response to methotrexate. | 2001 Jun |
|
Aromatic quinolinecarboxamides as selective, orally active antibody production inhibitors for prevention of acute xenograft rejection. | 2001 Jun 7 |
|
Novel therapies for anti-neutrophil cytoplasmic antibody-associated vasculitis. | 2001 Mar |
|
Comorbidity in rheumatoid arthritis. | 2001 May |
|
Leflunomide induces apoptosis of thymocytes and T-cell hybridoma: differences in sensitivity and signaling pathways. | 2001 May |
|
Inhibition of cyclosporin-resistant B-cell antigen responses by pyrazoles: a tool for the identification of novel molecular mechanisms of B-cell activation. | 2001 May |
|
Modulation of human peripheral blood mononuclear cell activation by the combination of leflunomide and pentoxifylline. | 2001 May |
|
Leflunomide and its analogue X920715 synergize with cyclosporin A in preventing early graft failure and delaying graft rejection of xenogeneic islets in nonobese diabetic mice. | 2001 May |
|
Have the new drugs relieved the burden of the orthopedic surgeon? | 2001 May |
|
Rationally designed anti-mitotic agents with pro-apoptotic activity. | 2001 Nov |
|
[Leflunomide--a new disease modifying anti-rheumatic agent]. | 2001 Nov 10 |
|
Platelet-derived growth factor receptors: a therapeutic target in solid tumors. | 2001 Oct |
|
Current and emerging lupus treatments. | 2001 Oct |
|
Leflunomide for the treatment of systemic lupus erythematosus: comment on the article by McMurray. | 2001 Oct |
|
Etanercept therapy for immune-mediated cochleovestibular disorders: preliminary results in a pilot study. | 2001 Sep |
|
Suppression of experimental autoimmune neuritis by leflunomide. | 2001 Sep |
|
Economic comparison of leflunomide and methotrexate in patients with rheumatoid arthritis: an evaluation based on a 1-year randomised controlled trial. | 2002 |
|
Comparative assessment of leflunomide and methotrexate for the treatment of rheumatoid arthritis, by dynamic enhanced magnetic resonance imaging. | 2002 Feb |
|
Experiences with leflunomide in solid organ transplantation. | 2002 Feb 15 |
|
A77 1726 induces differentiation of human myeloid leukemia K562 cells by depletion of intracellular CTP pools. | 2002 Sep |
|
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. | 2015 May 18 |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:12:11 UTC 2023
by
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on
Wed Jul 05 23:12:11 UTC 2023
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Record UNII |
1C058IKG3B
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Record Status |
Validated (UNII)
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Record Version |
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LIVERTOX |
NBK548525
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WHO-VATC |
QL04AA31
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NCI_THESAURUS |
C471
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EMA ASSESSMENT REPORTS |
AUBAGIO (AUTHORIZED: MULTIPLE SCLEROSIS)
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NDF-RT |
N0000185502
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WHO-ATC |
L04AA31
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DB08880
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68540
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54684141
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SUB25218
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1357056
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C527525
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TERIFLUNOMIDE
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YY-88
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1C058IKG3B
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Teriflunomide
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7761
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100000089234
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N0000185501
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PRIMARY | Dihydroorotate Dehydrogenase Inhibitors [MoA] | ||
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M10578
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CHEMBL973
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108605-62-5
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C76662
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1C058IKG3B
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1310520
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163451-81-8
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Related Record | Type | Details | ||
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METABOLIC ENZYME -> NON-SUBSTRATE | |||
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METABOLIC ENZYME -> NON-SUBSTRATE | |||
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EXCRETED UNCHANGED |
FECAL
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TRANSPORTER -> INHIBITOR |
Terifluniomide is an inhibitor of BCRP, OAT3, OATP1B1, OCT2 in vitro
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TRANSPORTER -> INHIBITOR |
Terifluniomide is an inhibitor of BCRP, OAT3, OATP1B1, OCT2 in vitro
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EXCRETED UNCHANGED |
URINE
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TRANSPORTER -> INHIBITOR |
Terifluniomide is an inhibitor of BCRP, OAT3, OATP1B1, OCT2 in vitro
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TARGET -> INHIBITOR |
INHIBITOR
IC50
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METABOLIC ENZYME -> NON-SUBSTRATE | |||
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METABOLIC ENZYME -> NON-SUBSTRATE | |||
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METABOLIC ENZYME -> NON-SUBSTRATE | |||
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METABOLIC ENZYME -> NON-SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR |
Terifluniomide is an inhibitor of BCRP, OAT3, OATP1B1, OCT2 in vitro
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TRANSPORTER -> SUBSTRATE |
Teriflunomide is a substrate of BCRP in vitro
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METABOLIC ENZYME -> NON-SUBSTRATE | |||
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METABOLIC ENZYME -> NON-SUBSTRATE | |||
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> NON-SUBSTRATE | |||
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METABOLIC ENZYME -> NON-SUBSTRATE |
Related Record | Type | Details | ||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
MINOR
URINE
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METABOLITE -> PARENT |
MINOR
URINE
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
MINOR
URINE
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METABOLITE -> PARENT |
4-TFMA was not detected in the single dose metabolism study, but was detected in very small amount after repeated dosing in clinical trials 4-TFMA plasma concentrations were measurable at relatively low concentrations after repeated teriflunomide doses of 7 mg (≤1.7 ng/mL) and 14 mg (≤5.31 ng/mL) for 468 weeks.
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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DOSE |
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Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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