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1357056

USP

Leflunomide Related Compound B

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

2-Cyano-3-hydroxy-N-(4-trifluoromethylphenyl)crotonamide

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About This Item

Empirical Formula (Hill Notation):
C12H9F3N2O2
CAS Number:
108605-62-5
Molecular Weight:
270.21
MDL number:
MFCD00910058
UNSPSC Code:
41116107
PubChem Substance ID:
329750239
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

leflunomide

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

SMILES string

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

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

Gene Information

human ... DHODH(1723)

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General description

Leflunomide Related Compound B (2-Cyano-3-hydroxy-N-(4-trifluoromethylphenyl)crotonamide is a malononitrilamide which is a water soluble metabolite of Leflunomide. It is considered as a noncompetitive inhibitor of dihydro-orotate dehydrogensae. This metabolite has been reported to initially target activated lymphocytes.

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

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pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Titia E Vrenken et al.
Journal of hepatology, 49(5), 799-809 (2008-09-24)
Leflunomide is used in the treatment of autoimmune diseases as an anti-inflammatory agent. Leflunomide and its active metabolite A77 1726 modulate mitogen-activated protein kinases (MAPK), Src kinases, the phosphoinositide-3 kinase (PI3K)/Akt-pathway and nuclear factor (NF)-kappaB activation. Both cell protective and
Eva Bernhoff et al.
Journal of virology, 84(4), 2150-2156 (2009-12-04)
The immunomodulatory drug leflunomide is frequently used for treating polyomavirus-associated nephropathy, yet its antiviral mechanism is unclear. We characterized the effects of the active leflunomide metabolite A771726 (LEF-A) on the polyomavirus BK (BKV) life cycle in human renal tubular epithelial
Takeo Sato et al.
Rheumatology (Oxford, England), 48(10), 1265-1268 (2009-08-05)
To elucidate the factors associated with poor prognosis of LEF-induced lung injury in patients with RA. The background and clinical and laboratory features of LEF-induced lung injury were examined and compared between patients who died of and who recovered from
Paola Montagna et al.
Annals of the New York Academy of Sciences, 1193, 30-35 (2010-04-20)
Rheumatoid arthritis (RA) prevalence is greater in females than in males, supporting estrogens as modulators of immune response. Leflunomide (LEF) is employed in the RA treatment. We studied the combinatory effects of LEF active metabolite A77 1726 (LEF-M) and 17beta-estradiol
Li-Xia Xiong et al.
Xi bao yu fen zi mian yi xue za zhi = Chinese journal of cellular and molecular immunology, 25(1), 16-19 (2009-01-08)
To observe the inhibitory effects of tyrosine kinases inhibitor A77 1726 on collagen generation induced by IL-13 in fibroblasts. The inhibition rate of fibroblast proliferation with different concentration of A77 1726 was observed by MTT method. The fibroblasts were divided
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