A77 1726 CAS: 163451-81-8
MF: C12H9F3N2O2
MW: 270.21
An active metabolite of leflunomide that inhibits Cox-2.

A77 1726 (CAS 163451-81-8)

A77 1726 | CAS 163451-81-8 is rated 5.0 out of 5 by 1.
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Alternate Names: A 1726, A77-1726, A771726, Flucyamide, HMR 1726, N-(4-Trifluoromethylphenyl)-2-cyano-3-hydroxycrotoamide, SU 20
Application: A77 1726 is an active metabolite of leflunomide that inhibits Cox-2
CAS Number: 163451-81-8
Purity: ≥98%
Molecular Weight: 270.21
Molecular Formula: C12H9F3N2O2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data (including water content).

A77 1726, also known as teriflunomide, is the active metabolite of leflunomide (sc-202209). This compound has demonstrated antiinflammatory, antiproliferative, and immunosuppressive effects. A77 1726 has been shown to inhibit the proliferation of multiple mammalian cell lines in vitro, has demonstrated inhibition of Cox-2, dendritic cell function, DHODH (dihydroorotate dehydrogenase), and blocks TNF-dependent nuclear factor-κ B activation and gene expression. DHODH is an enzyme involved in the de novo synthesis of pyrimidine nucleotides, and its inhibition is thought to result in the antiproliferative effects on rapidly dividing cells, such as T-cells, observed by this compound.


References

1. Mattar, T., et al. 1993. FEBS Lett. 334: 161-164. PMID: 8224241
2. Xu, X., et al. 1995. J. Biol. Chem. 270: 12398-12403. PMID: 7759480
3. Xu, X., et al. 1996. Biochem. Pharmacol. 52: 527-534. PMID: 8759024
4. Davis, J.P., et al. 1996. Biochemistry. 35: 1270-1273. PMID: 8573583
5. Xu, X., et al. 1997. J. Immunol. 159: 167-174. PMID: 9200452
6. Elder, R.T., et al. 1997. J. Immunol. 159: 22-27. PMID: 9200434
7. Hamilton, L.C., et al. 1999. Br. J. Pharmacol. 127: 1589-1596. PMID: 10455314
8. Manna, S.K., et al. 1999. J. Immunol. 162: 2095-2102. PMID: 9973483
9. Kirsch, B.M., et al. 2005. Arthritis Res. Ther. 7: R694-R703. PMID: 15899055

Physical State :
Solid
Solubility :
Soluble in DMSO (32 mg/ml at 25° C), methanol, DMF (~21.6 mg/ml), ethanol (1.35 mg/ml, sonication), and water (slightly).
Storage :
Store at 4° C
Refractive Index :
n20D 1.55 (Predicted)
IC50 :
Prevents activated lymphocytes from accumulating sufficient pyrimidines to support DNA synthesis: IC50 = 0.09 µM (rat); Inhibit the production of prostaglandin E2 in synoviocytes activated by IL-1α: IC50 = 3 µM; Prevents activated lymphocytes from accumulating sufficient pyrimidines to support DNA synthesis: IC50 = 3.5 µM (mouse); Inhibit the production of prostaglandin E2 in synoviocytes activated by TNF-α: IC50 = 7 µM; Prevents activated lymphocytes from accumulating sufficient pyrimidines to support DNA synthesis: IC50 = 12.5 µM (human)
Ki Data :
Dihydroorotate dehydrogenase: Ki= 30 nM (human); Dihydroorotate dehydrogenase: Ki= 179 nM; DHODH: Ki= 22 µM (Plasmodium falciparum)
pK Values :
pKa: 5.2 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
RTECS :
EM2585115
PubChem CID :
54684141
Merck Index :
14: 9165
MDL Number :
MFCD00910058
SMILES :
C/C(=C(\\C#N)/C(=O)NC1=CC=C(C=C1)C(F)(F)F)/O

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Certificate of Analysis

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A77 1726 (CAS 163451-81-8)  Product Citations

See how others have used A77 1726 (CAS 163451-81-8). Click on the entry to view the PubMed entry .

Citations 1 to 10 of 11 total

PMID: # 25412347  Hung, HC. et al. 2014. PLoS ONE. 9: e111331.

PMID: # 15899055  Kirsch, BM. et al. 2005. Arthritis Res. Ther. 7: R694-R703.

PMID: # 9973483  Manna, SK. et al. 1999. J. Immunol. 162: 2095-2102.

PMID: # 10455314  Hamilton, LC. et al. 1999. Br. J. Pharmacol. 127: 1589-1596.

PMID: # 9200434  Elder, RT. et al. 1997. J. Immunol. 159: 22-27.

PMID: # 9200452  Xu, X. et al. 1997. J. Immunol. 159: 167-174.

PMID: # 8759024  Xu, X. et al. 1996. Biochem. Pharmacol. 52: 527-534.

PMID: # 8573583  Davis, JP. et al. 1996. Biochemistry. 35: 1270-1273.

PMID: # 7759480  Xu, X. et al. 1995. J. Biol. Chem. 270: 12398-12403.

PMID: # 8224241  Mattar, T. et al. 1993. FEBS Lett. 334: 161-164.

Citations 1 to 10 of 11 total
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Rated 5 out of 5 by from Kirsch et al Kirsch et al. (PubMed ID 15899055) found that dendritic cells (DC) differentiated in the presence of the active metabolite of leflunomide, A77 1726 (LEF-M), displayed reduced surface expression of CD40 as well as CD80 and led to unsuccessful DC cell maturation. -SCBT Publication Review
Date published: 2015-04-02
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