Teriflunomide

  • CAT Number: A000645
  • CAS Number: 108605-62-5
  • Molecular Formula: C12H9F3N2O2
  • Molecular Weight: 270.21
  • Purity: ≥95%
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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.

Catalog Number A000645
CAS Number 108605-62-5
Molecular Formula

C12H9F3N2O2

Purity 95%
Target DHODH
Solubility Soluble in DMSO > 10 mM
Storage Store at -20°C
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-
InChIKey UTNUDOFZCWSZMS-YFHOEESVSA-N
SMILES CC(=C(C#N)C(=O)NC1=CC=C(C=C1)C(F)(F)F)O
Reference

1: Mancinelli L, Amerio P, di Ioia M, Di Tommaso V, De Luca G, Onofrj M, Lugaresi
A. /Nail loss after teriflunomide treatment: A new potential adverse event/. Mult
Scler Relat Disord. 2017 Nov;18:170-172. doi: 10.1016/j.msard.2017.09.029. Epub
2017 Sep 25. PubMed PMID: 29141803.
<br>

2: Gandoglia I, Ivaldi F, Laroni A, Benvenuto F, Solaro C, Mancardi G, Kerlero de
Rosbo N, Uccelli A. Teriflunomide treatment reduces B cells in patients with MS.
Neurol Neuroimmunol Neuroinflamm. 2017 Oct 23;4(6):e403. doi:
10.1212/NXI.0000000000000403. eCollection 2017 Nov. PubMed PMID: 29082295; PubMed
Central PMCID: PMC5656406.
<br>

3: Robertson D, Dixon C, Aungst A, McCoy B, Moreo N, Casady L, Maldonado J.
Tolerability and efficacy of colestipol hydrochloride for accelerated elimination
of teriflunomide. Expert Rev Clin Pharmacol. 2017 Nov 2:1-5. doi:
10.1080/17512433.2017.1395280. [Epub ahead of print] PubMed PMID: 29064296.

<br>
4: Landais A, Alhendi R, Gouverneur A, Teron-Aboud B. A case of lymphoma in a
patient on teriflunomide treatment for relapsing multiple sclerosis. Mult Scler
Relat Disord. 2017 Oct;17:92-94. doi: 10.1016/j.msard.2017.07.001. Epub 2017 Jul
3. PubMed PMID: 29055483.
<br>

5: Coyle PK, Khatri B, Edwards KR, Meca-Lallana JE, Cavalier S, Rufi P, Benamor
M, Brette S, Robinson M, Gold R; Teri-PRO Trial Group. Patient-reported outcomes
in relapsing forms of MS: Real-world, global treatment experience with
teriflunomide from the Teri-PRO study. Mult Scler Relat Disord. 2017
Oct;17:107-115. doi: 10.1016/j.msard.2017.07.006. Epub 2017 Jul 6. PubMed PMID:
29055438.
<br>

6: Jiang L, Zhang W, Li W, Ling C, Jiang M. Anti-inflammatory drug, leflunomide
and its metabolite teriflunomide inhibit NSCLC proliferation in vivo and in
vitro. Toxicol Lett. 2018 Jan 5;282:154-165. doi: 10.1016/j.toxlet.2017.10.013.
Epub 2017 Oct 16. PubMed PMID: 29050931.

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7: Imanishi S, Takahashi R, Katagiri S, Kobayashi C, Umezu T, Ohyashiki K,
Ohyashiki JH. Teriflunomide restores 5-azacytidine sensitivity via activation of
pyrimidine salvage in 5-azacytidine-resistant leukemia cells. Oncotarget. 2017
Jul 22;8(41):69906-69915. doi: 10.18632/oncotarget.19436. eCollection 2017 Sep
19. PubMed PMID: 29050250; PubMed Central PMCID: PMC5642525.

<br>
8: Gilli F, Li L, Royce DB, DiSano KD, Pachner AR. Treatment of Theiler/’s
virus-induced demyelinating disease with teriflunomide. J Neurovirol. 2017 Sep
14. doi: 10.1007/s13365-017-0570-8. [Epub ahead of print] PubMed PMID: 28913765.
<br>

9: Dereure O, Camu W. Teriflunomide-induced psoriasiform changes of fingernails:
a new example of paradoxical side effect? Int J Dermatol. 2017
Dec;56(12):1479-1481. doi: 10.1111/ijd.13742. Epub 2017 Sep 7. PubMed PMID:
28884799.

<br>
10: Yamout BI, Said M, Hannoun S, Zeineddine M, Massouh J, Khoury SJ. Rebound
syndrome after teriflunomide cessation in a patient with multiple sclerosis. J
Neurol Sci. 2017 Sep 15;380:79-81. doi: 10.1016/j.jns.2017.07.014. Epub 2017 Jul
9. PubMed PMID: 28870594.

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