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L5025

Leflunomide

≥98% (TLC), T cell proliferation inhibitor, powder

Synonym(s):

5-Methylisoxazole-4-(4-trifluoromethyl)carboxanilide

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About This Item

Empirical Formula (Hill Notation):
C12H9F3N2O2
CAS Number:
75706-12-6
Molecular Weight:
270.21
UNSPSC Code:
12352202
PubChem Substance ID:
24278516
NACRES:
NA.77
MDL number:
MFCD00867593
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Product Name

Leflunomide, Immunosuppressant

Quality Level

200

assay

≥98% (TLC)

form

powder

mp

166.5 °C

solubility

methanol: 19.60-20.40 mg/mL, clear, colorless to faintly yellow

mode of action

enzyme | inhibits

storage temp.

2-8°C

SMILES string

Cc1oncc1C(=O)Nc2ccc(cc2)C(F)(F)F

InChI

1S/C12H9F3N2O2/c1-7-10(6-16-19-7)11(18)17-9-4-2-8(3-5-9)12(13,14)15/h2-6H,1H3,(H,17,18)

InChI key

VHOGYURTWQBHIL-UHFFFAOYSA-N

Gene Information

human ... DHODH(1723)

Application

By virtue of its immunosuppressant effects, leflunomide has found use in organ transplantation and treatment of rheumatoid arthritis and other autoimmune diseases.

Biochem/physiol Actions

Immunosuppressive; inhibits T and B cell proliferation. Activity is attributed mainly to its metabolite, a malononitrile derivative, which is believed to inhibit dihydroorotate dehydrogenase (in the de novo pyrimidine synthesis pathway) as well as several protein tyrosine kinases.

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pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000404021
0000404021
0000398580
0000398580
0000235443

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Nicolae Leca
Current opinion in organ transplantation, 14(4), 370-374 (2009-06-11)
Leflunomide has been used off-label in renal transplantation because of the attractive combination of antiviral and immunosuppressive effects. This study intends to review the clinical applications of leflunomide with interest to transplantation. In renal transplantation, particularly in BK nephropathy, the
X Xu et al.
Biochemical pharmacology, 52(4), 527-534 (1996-08-23)
Previous studies have demonstrated that the active metabolite of leflunomide, A77 1726 [N-(4-trifluoromethylphenyl-2-cyano-3-hydroxycrotoamide)], is capable of inhibiting the activities of tyrosine kinases and dihydroorotate dehydrogenase (DHO-DHase). In the present study, we define the relative contribution of these activities to the
T R Brazelton et al.
Current opinion in immunology, 8(5), 710-720 (1996-10-01)
Among all the new immunosuppressive molecules being investigated either preclinically or clinically, four stand out: tacrolimus (FK506), sirolimus (rapamycin), mycophenolate mofetil and leflunomide (and its malononitriloamide analogs). Each drug has distinct mechanisms of immunosuppressive action, and in the past year
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