Teriflunomide | A77-1726 | HMR1726 | CAS#108605-62-5 | CAS#163451-81-8 | Immunomodulatory drug

MedKoo Cat#: 205875 | Name: Teriflunomide

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Teriflunomide

CAS#108605-62-5

Theoretical Analysis

MedKoo Cat#: 205875

Name: Teriflunomide

CAS#: 108605-62-5

Chemical Formula: C12H9F3N2O2

Exact Mass: 270.0616

Molecular Weight: 270.21

Elemental Analysis: C, 53.34; H, 3.36; F, 21.09; N, 10.37; O, 11.84

Price and Availability

Size	Price	Availability
500mg	USD 150.00	Ready to ship
1g	USD 250.00	Ready to ship
2g	USD 350.00	Ready to ship
5g	USD 550.00	Ready to ship
10g	USD 850.00	Ready to ship
20g	USD 1,450.00	Ready to ship

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Related CAS #

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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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#BBC30720

QC Data

View QC data: current batch, Lot#BBC30720

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	27.0	99.96

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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:

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.

1: Shrestha BK, Sujakhu E, Karale S, Telagarapu VML. COVID-19 in patients with multiple sclerosis-A narrative review. Mult Scler Relat Disord. 2024 Dec 8;93:106221. doi: 10.1016/j.msard.2024.106221. Epub ahead of print. PMID: 39675123. 2: Mueller K, Pei S, Kuraitis D. Teriflunomide-related development of inverse psoriasis and worsening of pre-existing plaque psoriasis. Dermatol Online J. 2024 Aug 15;30(4). doi: 10.5070/D330464111. PMID: 39644471. 3: Schrell L, Fuchs HL, Dickmanns A, Scheibner D, Olejnik J, Hume AJ, Reineking W, Störk T, Müller M, Graaf-Rau A, Diederich S, Finke S, Baumgärtner W, Mühlberger E, Balkema-Buschmann A, Dobbelstein M. Inhibitors of dihydroorotate dehydrogenase synergize with the broad antiviral activity of 4'-fluorouridine. Antiviral Res. 2024 Dec 3;233:106046. doi: 10.1016/j.antiviral.2024.106046. Epub ahead of print. PMID: 39638153. 4: Framke E, Sellebjerg F, Kant M, Stilund M, Jensen HB, Illes Z, Asgari N, Sejbaek T, Roug LC, Jensen MB, Schäfer J, Rasmussen PV, Christensen JR, Weglewski A, Prakash S, Magyari M; DMSG study group*. Risk of hypertension in patients with multiple sclerosis treated with teriflunomide compared to dimethyl fumarate: A nationwide cohort study in Denmark. Mult Scler. 2024 Dec 4:13524585241299715. doi: 10.1177/13524585241299715. Epub ahead of print. PMID: 39632560. 5: Paybast S, Rezaeimanesh N, Naser Moghadasi A. De-escalation of anti-CD20 monoclonal antibodies to low-moderate efficacy disease-modifying treatments (DMTs) in patients with relapse-remitting multiple sclerosis: An initial Iranian experience. Caspian J Intern Med. 2024 Oct 19;16(1):126-131. doi: 10.22088/cjim.16.1.126. PMID: 39619757; PMCID: PMC11607104. 6: Aksoy D, Çevik B. Restless legs syndrome associated with teriflunomide use in two patients with multiple sclerosis. Clin Neurol Neurosurg. 2025 Jan;248:108665. doi: 10.1016/j.clineuro.2024.108665. Epub 2024 Nov 26. PMID: 39616829. 7: Etemadifar M, Ahmadi M, Salari M, Ansari B, Sedaghat N. Distal median nerve dysfunction and carpal tunnel syndrome in people with multiple sclerosis treated with teriflunomide: an electrodiagnostic study. Neurol Sci. 2024 Nov 30. doi: 10.1007/s10072-024-07898-7. Epub ahead of print. PMID: 39613939. 8: Li J, Hutton GJ, Varisco TJ, Lin Y, Essien EJ, Aparasu RR. Infection Risk Associated with High-Efficacy Disease-Modifying Agents in Multiple Sclerosis: A Retrospective Cohort Study. Clin Pharmacol Ther. 2024 Nov 15. doi: 10.1002/cpt.3492. Epub ahead of print. PMID: 39547934. 9: Szewczak L, Machcińska M, Kierasińska M, Zawadzka-Więch U, Maruszewska- Cheruiyot M, Majewski P, Karlińska A, Rola R, Donskow-Łysoniewska K. Expression of STAT- and T-cell-related genes in women with first-line treatment of relapsing-remitting multiple sclerosis. Scand J Immunol. 2025 Jan;101(1):e13424. doi: 10.1111/sji.13424. Epub 2024 Nov 15. PMID: 39545481. 10: Alshamrani FJG, Zafar A, Alsawad RM, Yasawy Z, Shahid R, Nazish S, Shariff E, Soltan NM. Achievement of No Evidence of Disease Activity-3 with Oral Disease-Modifying Treatment in Patients with Relapsing-Remitting Multiple Sclerosis. Saudi J Med Med Sci. 2024 Oct-Dec;12(4):299-305. doi: 10.4103/sjmms.sjmms_148_24. Epub 2024 Oct 12. PMID: 39539793; PMCID: PMC11556514. 11: Alvarez E, Steinman L, Fox EJ, Hartung HP, Qian P, Wray S, Robertson D, Selmaj K, Wynn D, Mok K, Xu Y, Bodhinathan K, Miskin HP, Cree BAC. Improvements in no evidence of disease activity with ublituximab vs. teriflunomide in the ULTIMATE phase 3 studies in relapsing multiple sclerosis. Front Neurol. 2024 Oct 24;15:1473284. doi: 10.3389/fneur.2024.1473284. PMID: 39512280; PMCID: PMC11542255. 12: Rezaee M, Ravangard R, Mojtabaeian SM, Jafari A. Cost-effectiveness of oral versus injectable disease modifying therapies in relapsing multiple sclerosis: a systematic review analysis. BMC Health Serv Res. 2024 Oct 28;24(1):1288. doi: 10.1186/s12913-024-11800-8. PMID: 39468560; PMCID: PMC11514832. 13: Fragkoudi A, Rumbold AR, Hall KA, Lechner-Scott J, Ilomäki J, Grzeskowiak LE. Sex differences in use of potentially teratogenic disease modifying treatments for multiple sclerosis and degree of hormonal contraception overlap in women between 2007-2021: An Australian population-based study. Mult Scler Relat Disord. 2024 Dec;92:105937. doi: 10.1016/j.msard.2024.105937. Epub 2024 Oct 10. PMID: 39427601. 14: Moles L, Otaegui-Chivite A, Gorostidi-Aicua M, Romarate L, Mendiburu I, Crespillo-Velasco H, Álvarez de Arcaya A, Ferreira E, Arruti M, Castillo-Triviño T, Otaegui D. Microbiota modulation by teriflunomide therapy in people with multiple sclerosis: An observational case-control study. Neurotherapeutics. 2024 Oct;21(6):e00457. doi: 10.1016/j.neurot.2024.e00457. Epub 2024 Oct 15. PMID: 39406600; PMCID: PMC11585876. 15: Karnam S, Jindal AB, Paul AT. Quality by design-based optimization of teriflunomide and quercetin combinational topical transferosomes for the treatment of rheumatoid arthritis. Int J Pharm. 2024 Dec 5;666:124829. doi: 10.1016/j.ijpharm.2024.124829. Epub 2024 Oct 13. PMID: 39406305. 16: Zivadinov R, Keenan AJ, Le HH, Ait-Tihyaty M, Gandhi K, Zierhut ML, Salvo- Halloran EM, Ramirez AO, Vuong V, Singh S, Hutton B. Brain volume loss in relapsing multiple sclerosis: indirect treatment comparisons of available disease-modifying therapies. BMC Neurol. 2024 Oct 8;24(1):378. doi: 10.1186/s12883-024-03888-6. PMID: 39379875; PMCID: PMC11460132. 17: Yang L, Ma D, Liu S, Zou L. The DHODH inhibitor teriflunomide impedes cell proliferation and enhances chemosensitivity to daunorubicin (DNR) in T-cell acute lymphoblastic leukemia. Ann Hematol. 2024 Oct 8. doi: 10.1007/s00277-024-05998-0. Epub ahead of print. PMID: 39377943. 18: Shirani A, Saez-Calveras N, Antel JP, Yaqubi M, Moore W, Brewster AL, Stuve O. Exploring the association of disease-modifying therapies for multiple sclerosis and BTK inhibitors with epilepsy. Ther Adv Neurol Disord. 2024 Sep 21;17:17562864241276204. doi: 10.1177/17562864241276204. PMID: 39371642; PMCID: PMC11456174. 19: Zewail M. Leflunomide nanocarriers: a new prospect of therapeutic applications. J Microencapsul. 2024 Dec;41(8):715-738. doi: 10.1080/02652048.2024.2407373. Epub 2024 Sep 25. PMID: 39320955. 20: Montalban X, Vermersch P, Arnold DL, Bar-Or A, Cree BAC, Cross AH, Kubala Havrdova E, Kappos L, Stuve O, Wiendl H, Wolinsky JS, Dahlke F, Le Bolay C, Shen Loo L, Gopalakrishnan S, Hyvert Y, Javor A, Guehring H, Tenenbaum N, Tomic D; evolutionRMS investigators. Safety and efficacy of evobrutinib in relapsing multiple sclerosis (evolutionRMS1 and evolutionRMS2): two multicentre, randomised, double-blind, active-controlled, phase 3 trials. Lancet Neurol. 2024 Nov;23(11):1119-1132. doi: 10.1016/S1474-4422(24)00328-4. Epub 2024 Sep 19. PMID: 39307151.