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Key Documents

SML0936

Sigma-Aldrich

Teriflunomide

≥98% (HPLC)

Synonym(s):

(Z)-2-Cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-2-butenamide, A 1726, A77-1726, A771726, Flucyamide, HMR 1726, N-(4-Trifluoromethylphenyl)-2-cyano-3-hydroxycrotoamide, SU 20

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About This Item

Empirical Formula (Hill Notation):
C12H9F3N2O2
CAS Number:
163451-81-8
Molecular Weight:
270.21
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL, clear (warmed)

storage temp.

−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-

InChI key

UTNUDOFZCWSZMS-YFHOEESVSA-N

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Application

Teriflunomide has been used as a dihydroorotate dehydrogenase (DHODH) inhibitor.

Biochem/physiol Actions

Teriflunomide is an orally available anti-inflammatory immunomodulator. It blocks the activity of dihydroorotate dehydrogenase, preventing pyrimidine synthesis and T and B cell proliferation and function. Teriflunomide has been used to treat rheumatoid arthritis and was recently approved for multiple sclerosis.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Inhibition of dihydroorotate dehydrogenase overcomes differentiation blockade in acute myeloid leukemia.
Sykes D B, et al.
Cell, 167(1), 171-186 (2016)
Mieradilijiang Abudupataer et al.
eLife, 10 (2021-09-07)
Bicuspid aortic valve (BAV) is the most common congenital cardiovascular disease in general population and is frequently associated with the development of thoracic aortic aneurysm (TAA). There is no effective strategy to intervene with TAA progression due to an incomplete
Andrea Bilger et al.
Oncotarget, 8(27), 44266-44280 (2017-06-03)
EBV infection causes mononucleosis and is associated with specific subsets of B cell lymphomas. Immunosuppressed patients such as organ transplant recipients are particularly susceptible to EBV-induced lymphoproliferative disease (LPD), which can be fatal. Leflunomide (a drug used to treat rheumatoid
Deepti Mathur et al.
Cancer discovery, 7(4), 380-390 (2017-03-04)
Metabolic changes induced by oncogenic drivers of cancer contribute to tumor growth and are attractive targets for cancer treatment. Here, we found that increased growth of PTEN-mutant cells was dependent on glutamine flux through the de novo pyrimidine synthesis pathway
Zhen-Guo Ma et al.
Clinical science (London, England : 1979), 132(6), 685-699 (2018-03-16)
T-cell infiltration and the subsequent increased intracardial chronic inflammation play crucial roles in the development of cardiac hypertrophy and heart failure (HF). A77 1726, the active metabolite of leflunomide, has been reported to have powerful anti-inflammatory and T cell-inhibiting properties.
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