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163451-81-8,MFCD00910058
Catalog No.:AA001U1C

163451-81-8 | Teriflunomide

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1mg
98%
in stock  
$6.00   $4.00
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10mg
98%
in stock  
$34.00   $24.00
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100mg
98%
in stock  
$51.00   $36.00
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250mg
98%
in stock  
$62.00   $43.00
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1g
97%
in stock  
$204.00   $143.00
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5g
97%
in stock  
$474.00   $332.00
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25g
97%
in stock  
$1,547.00   $1,083.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA001U1C
Chemical Name:
Teriflunomide
CAS Number:
163451-81-8
Molecular Formula:
C12H9F3N2O2
Molecular Weight:
270.2073
MDL Number:
MFCD00910058
SMILES:
N#C/C(=C(/O)\C)/C(=O)Nc1ccc(cc1)C(F)(F)F
Properties
Computed Properties
 
Complexity:
426  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
2  
XLogP3:
3.3  

Downstream Synthesis Route
75706-12-6   
teriflunomide 

[1]Patent:US2017/73304,2017,A1.Locationinpatent:Paragraph0025

[2]Patent:WO2016/203410,2016,A1.Locationinpatent:Page/Pagecolumn16;17;18;19

[3]Chemicalandpharmaceuticalbulletin,2003,vol.51,p.313-314

[4]Patent:US5494911,1996,A

[5]Patent:US5504084,1996,A

[6]Patent:US5519042,1996,A

[7]ChemicalCommunications,2012,vol.48,p.11781-11783

[8]ChemicalPhysicsLetters,2014,vol.613,p.127-132

[9]GreenChemistry,2017,vol.19,p.2541-2545

[10]ChemCatChem,2019,vol.11,p.1425-1430

CASUnavailable 
  1206724-43-7    163451-81-8 

[1]CurrentPatentAssignee:ALEMBICPHARMACEUTICALSLIMITED-WO2010/13159,2010,A1Locationinpatent:Page/Pagecolumn7

[1]CurrentPatentAssignee:ZYDUSLIFESCIENCESLTD-US2016/58730,2016,A1

Literature

Title: Mitochondrial dysfunction induced by leflunomide and its active metabolite.

Journal: Toxicology 20180301

Title: Fingerprinting of neurotoxic compounds using a mouse embryonic stem cell dual luminescence reporter assay.

Journal: Archives of toxicology 20170101

Title: Long-term safety and efficacy of teriflunomide: Nine-year follow-up of the randomized TEMSO study.

Journal: Neurology 20160308

Title: Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.

Journal: Chemical research in toxicology 20150518

Title: Novel selective and potent inhibitors of malaria parasite dihydroorotate dehydrogenase: discovery and optimization of dihydrothiophenone derivatives.

Journal: Journal of medicinal chemistry 20131024

Title: On dihydroorotate dehydrogenases and their inhibitors and uses.

Journal: Journal of medicinal chemistry 20130425

Title: Discovery of diverse human dihydroorotate dehydrogenase inhibitors as immunosuppressive agents by structure-based virtual screening.

Journal: Journal of medicinal chemistry 20121011

Title: New inhibitors of dihydroorotate dehydrogenase (DHODH) based on the 4-hydroxy-1,2,5-oxadiazol-3-yl (hydroxyfurazanyl) scaffold.

Journal: European journal of medicinal chemistry 20120301

Title: Biaryl analogues of teriflunomide as potent DHODH inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20111215

Title: Hepatic cytochrome P450s attenuate the cytotoxicity induced by leflunomide and its active metabolite A77 1726 in primary cultured rat hepatocytes.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20110801

Title: 1,2,5-Oxadiazole analogues of leflunomide and related compounds.

Journal: European journal of medicinal chemistry 20110101

Title: Structure-based design, synthesis, and characterization of inhibitors of human and Plasmodium falciparum dihydroorotate dehydrogenases.

Journal: Journal of medicinal chemistry 20090514

Title: ATP competitive inhibitors of D-alanine-D-alanine ligase based on protein kinase inhibitor scaffolds.

Journal: Bioorganic & medicinal chemistry 20090201

Title: Dihydroorotate dehydrogenase inhibitor A771726 (leflunomide) induces apoptosis and diminishes proliferation of multiple myeloma cells.

Journal: Molecular cancer therapeutics 20090201

Title: Spotlight on teriflunomide.

Journal: International MS journal 20080601

Title: The immunomodulatory drug Leflunomide inhibits cell cycle progression of B-CLL cells.

Journal: Leukemia 20080301

Title: Design and synthesis of potent inhibitors of the malaria parasite dihydroorotate dehydrogenase.

Journal: Journal of medicinal chemistry 20070125

Title: A Phase II study of the safety and efficacy of teriflunomide in multiple sclerosis with relapses.

Journal: Neurology 20060328

Title: SAR, species specificity, and cellular activity of cyclopentene dicarboxylic acid amides as DHODH inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20051101

Title: [The active metabolite of leflunomide A771726 inhibits proliferation and collagen synthesis of hepatic stellate cell].

Journal: Zhejiang da xue xue bao. Yi xue ban = Journal of Zhejiang University. Medical sciences 20041101

Title: A77 1726 induces differentiation of human myeloid leukemia K562 cells by depletion of intracellular CTP pools.

Journal: Molecular pharmacology 20020901

Title: Inhibition of HIV replication by A77 1726, the active metabolite of leflunomide, in combination with pyrimidine nucleoside reverse transcriptase inhibitors.

Journal: Journal of acquired immune deficiency syndromes (1999) 20011001

Title: Recombinant expression of N-terminal truncated mutants of the membrane bound mouse, rat and human flavoenzyme dihydroorotate dehydrogenase. A versatile tool to rate inhibitor effects?

Journal: European journal of biochemistry 20010301

Title: New dermatological agents for the treatment of psoriasis.

Journal: Journal of medicinal chemistry 20010201

Title: Immunosuppressive leflunomide metabolite (A77 1726) blocks TNF-dependent nuclear factor-kappa B activation and gene expression.

Journal: Journal of immunology (Baltimore, Md. : 1950) 19990215

Title: Species-related inhibition of human and rat dihydroorotate dehydrogenase by immunosuppressive isoxazol and cinchoninic acid derivatives.

Journal: Biochemical pharmacology 19981101

Title: Structural and functional comparison of agents interfering with dihydroorotate, succinate and NADH oxidation of rat liver mitochondria.

Journal: Biochemical pharmacology 19981015

Title: 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.

Journal: Biochemical pharmacology 19980501

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