Teriflunomide
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MedKoo CAT#: 205875

CAS#: 108605-62-5

Description: Teriflunomide, aslo known as A77 1726, is the active metabolite of leflunomide. Teriflunomide is an immunomodulatory drug inhibiting pyrimidine de novo synthesis by blocking the enzyme dihydroorotate dehydrogenase. It is uncertain whether this explains its effect on MS lesions. Teriflunomide inhibits rapidly dividing cells, including activated T cells, which are thought to drive the disease process in MS. It has been found that teriflunomide blocks the transcription factor NF-κB. The drug was approved by the FDA on September 13, 2012.

Chemical Structure

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Teriflunomide
CAS# 108605-62-5
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 205875
Name: Teriflunomide
CAS#: 108605-62-5
Chemical Formula: C12H9F3N2O2
Exact Mass: 270.06
Molecular Weight: 270.207
Elemental Analysis: C, 53.34; H, 3.36; F, 21.09; N, 10.37; O, 11.84

Price and Availability

Size Price Availability Quantity
500mg USD 150 Ready to ship
1g USD 250 Ready to ship
2g USD 350 Ready to ship
5g USD 550 Ready to ship
10g USD 850 Ready to ship
20g USD 1450 Ready to ship
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Synonym: A77 1726; A771726; A-771726; HMR1726; HMR-1726; HMR 1726; teriflunomide; Brande name: Aubagio.

IUPAC/Chemical Name: (Z)-2-cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)but-2-enamide.

InChi Key: UTNUDOFZCWSZMS-YFHOEESVSA-N

InChi Code: 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-

SMILES Code: C/C(O)=C(C#N)/C(NC1=CC=C(C(F)(F)F)C=C1)=O

Appearance: White to off-white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target: Teriflunomide (A77 1726, HMR-1726) inhibits pyrimidine de novo synthesis by blocking the enzyme dihydroorotate dehydrogenase, used as an immunomodulatory agent.
In vitro activity: After culture with teriflunomide 50 μM, both CD8+ and CD4+ T cells showed a reduction in spontaneous lymphoproliferation (figure 2A). Group analysis of spontaneous CD8+ T-cell proliferation in 12 patients with HAM/TSP showed a significant and concentration-dependent suppression in culture with teriflunomide at day 5 (p = 0.0025; figure 2B). The average percent inhibition across all the patients with HAM/TSP was 54.3%, 64.1%, and 84.9% at 25, 50, and 100 μM teriflunomide, respectively (figure 2C), which was consistent with proliferation assay using [3H] thymidine (figure 1E). Reference: Neurol Neuroimmunol Neuroinflamm. 2021 May; 8(3): e986. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8054963/
In vivo activity: Compared with baseline, i.c.v. TERI (Teriflunomide) injection caused a stable decrease of ∼60% in the MFR of CA1 neurons (Figures 6A–6C). In contrast, similar amount of VEH did not affect the MFR across several hours of recording (Figure 6D; Figure S9D). These results reveal an inhibitory effect of TERI on spontaneous spiking activity in the hippocampus of behaving mice. Reference: Neuron. 2019 Jun 5; 102(5): 1009–1024.e8. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6559804/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 27.0 99.96

Preparing Stock Solutions

The following data is based on the product molecular weight 270.21 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Enose-Akahata Y, Ngouth N, Ohayon J, Mandel M, Chavin J, Turner TJ, Jacobson S. Effect of Teriflunomide on Cells From Patients With Human T-cell Lymphotropic Virus Type 1-Associated Neurologic Disease. Neurol Neuroimmunol Neuroinflamm. 2021 Apr 9;8(3):e986. doi: 10.1212/NXI.0000000000000986. PMID: 33837058; PMCID: PMC8054963. 2. Wolters A, Reuther J, Gude P, Weber T, Theiss C, Vogelsang H, Matschke V. Teriflunomide provides protective properties after oxygen-glucose-deprivation in hippocampal and cerebellar slice cultures. Neural Regen Res. 2021 Nov;16(11):2243-2249. doi: 10.4103/1673-5374.310689. PMID: 33818508. 3. Styr B, Gonen N, Zarhin D, Ruggiero A, Atsmon R, Gazit N, Braun G, Frere S, Vertkin I, Shapira I, Harel M, Heim LR, Katsenelson M, Rechnitz O, Fadila S, Derdikman D, Rubinstein M, Geiger T, Ruppin E, Slutsky I. Mitochondrial Regulation of the Hippocampal Firing Rate Set Point and Seizure Susceptibility. Neuron. 2019 Jun 5;102(5):1009-1024.e8. doi: 10.1016/j.neuron.2019.03.045. Epub 2019 Apr 29. PMID: 31047779; PMCID: PMC6559804. 4. Prabhakara KS, Kota DJ, Jones GH, Srivastava AK, Cox CS Jr, Olson SD. Teriflunomide Modulates Vascular Permeability and Microglial Activation after Experimental Traumatic Brain Injury. Mol Ther. 2018 Sep 5;26(9):2152-2162. doi: 10.1016/j.ymthe.2018.06.022. Epub 2018 Jul 5. PMID: 30037655; PMCID: PMC6127507.
In vitro protocol: 1. Enose-Akahata Y, Ngouth N, Ohayon J, Mandel M, Chavin J, Turner TJ, Jacobson S. Effect of Teriflunomide on Cells From Patients With Human T-cell Lymphotropic Virus Type 1-Associated Neurologic Disease. Neurol Neuroimmunol Neuroinflamm. 2021 Apr 9;8(3):e986. doi: 10.1212/NXI.0000000000000986. PMID: 33837058; PMCID: PMC8054963. 2. Wolters A, Reuther J, Gude P, Weber T, Theiss C, Vogelsang H, Matschke V. Teriflunomide provides protective properties after oxygen-glucose-deprivation in hippocampal and cerebellar slice cultures. Neural Regen Res. 2021 Nov;16(11):2243-2249. doi: 10.4103/1673-5374.310689. PMID: 33818508.
In vivo protocol: 1. Styr B, Gonen N, Zarhin D, Ruggiero A, Atsmon R, Gazit N, Braun G, Frere S, Vertkin I, Shapira I, Harel M, Heim LR, Katsenelson M, Rechnitz O, Fadila S, Derdikman D, Rubinstein M, Geiger T, Ruppin E, Slutsky I. Mitochondrial Regulation of the Hippocampal Firing Rate Set Point and Seizure Susceptibility. Neuron. 2019 Jun 5;102(5):1009-1024.e8. doi: 10.1016/j.neuron.2019.03.045. Epub 2019 Apr 29. PMID: 31047779; PMCID: PMC6559804. 2. Prabhakara KS, Kota DJ, Jones GH, Srivastava AK, Cox CS Jr, Olson SD. Teriflunomide Modulates Vascular Permeability and Microglial Activation after Experimental Traumatic Brain Injury. Mol Ther. 2018 Sep 5;26(9):2152-2162. doi: 10.1016/j.ymthe.2018.06.022. Epub 2018 Jul 5. PMID: 30037655; PMCID: PMC6127507.

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1: Oh J, O'Connor PW. An update of teriflunomide for treatment of multiple sclerosis. Ther Clin Risk Manag. 2013;9:177-90. doi: 10.2147/TCRM.S30947. Epub 2013 Apr 26. PubMed PMID: 23761970.

2: Oh J, O'Connor PW. Teriflunomide for the treatment of multiple sclerosis. Semin Neurol. 2013 Feb;33(1):45-55. doi: 10.1055/s-0033-1343795. Epub 2013 May 25. PubMed PMID: 23709212.

3: Warnke C, Meyer Zu Hörste G, Menge T, Stüve O, Hartung HP, Wiendl H, Kieseier BC. [Teriflunomide for treatment of multiple sclerosis]. Nervenarzt. 2013 Jun;84(6):724-31. doi: 10.1007/s00115-013-3779-7. German. PubMed PMID: 23695001.

4: Wiese MD, Rowland A, Polasek TM, Sorich MJ, O'Doherty C. Pharmacokinetic evaluation of teriflunomide for the treatment of multiple sclerosis. Expert Opin Drug Metab Toxicol. 2013 May 17. [Epub ahead of print] PubMed PMID: 23682862.

5: Tanasescu R, Evangelou N, Constantinescu CS. Role of oral teriflunomide in the management of multiple sclerosis. Neuropsychiatr Dis Treat. 2013;9:539-53. doi: 10.2147/NDT.S31248. Epub 2013 Apr 22. PubMed PMID: 23637535; PubMed Central PMCID: PMC3639219.

6: Hussar DA, Hurrey NJ. Aclidinium bromide, tofacitinib citrate, and teriflunomide. J Am Pharm Assoc (2003). 2013 Jan 1;53(1):106-10. doi: 10.1331/JAPhA.2013.13504. PubMed PMID: 23636164.

7: Xi H, Cun D, Xiang R, Guan Y, Zhang Y, Li Y, Fang L. Intra-articular drug delivery from an optimized topical patch containing teriflunomide and lornoxicam for rheumatoid arthritis treatment: Does the topical patch really enhance a local treatment? J Control Release. 2013 Apr 6;169(1-2):73-81. doi: 10.1016/j.jconrel.2013.03.028. [Epub ahead of print] PubMed PMID: 23567043.

8: Wolinsky JS, Narayana PA, Nelson F, Datta S, O'Connor P, Confavreux C, Comi G, Kappos L, Olsson TP, Truffinet P, Wang L, Miller A, Freedman MS; for the Teriflunomide Multiple Sclerosis Oral (TEMSO) Trial Group. Magnetic resonance imaging outcomes from a phase III trial of teriflunomide. Mult Scler. 2013 Feb 27. [Epub ahead of print] PubMed PMID: 23447359.

9: He D, Xu Z, Dong S, Zhang H, Zhou H, Wang L, Zhang S. Teriflunomide for multiple sclerosis. Cochrane Database Syst Rev. 2012 Dec 12;12:CD009882. doi: 10.1002/14651858.CD009882.pub2. Review. PubMed PMID: 23235682.

10: Papadopoulou A, Kappos L, Sprenger T. Teriflunomide for oral therapy in multiple sclerosis. Expert Rev Clin Pharmacol. 2012 Nov;5(6):617-28. doi: 10.1586/ecp.12.56. PubMed PMID: 23234322.