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Merck
CN

SML4100

Vidofludimus

≥98% (HPLC)

Synonym(s):

IMU-838, 2-((3-Fluoro-3′-methoxy-[1,1′-biphenyl]-4-yl)carbamoyl)cyclopent-1-enecarboxylic acid, 2-[[(3-Fluoro-3′-methoxy[1,1′-biphenyl]-4-yl)amino]carbonyl]-1-cyclopentene-1-carboxylic acid, 2-[[2-Fluoro-4-(3-methoxyphenyl)phenyl]carbamoyl]cyclopentene-1-carboxylic acid, 4SC-101, IMU 838, IMU838, SC12267

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About This Item

Empirical Formula (Hill Notation):
C20H18FNO4
CAS Number:
Molecular Weight:
355.36
MDL number:
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Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to yellow

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

SMILES string

Fc1c(ccc(c1)c3cc(ccc3)OC)NC(=O)C2=C(CCC2)C(=O)O

InChI

1S/C20H18FNO4/c1-26-14-5-2-4-12(10-14)13-8-9-18(17(21)11-13)22-19(23)15-6-3-7-16(15)20(24)25/h2,4-5,8-11H,3,6-7H2,1H3,(H,22,23)(H,24,25)

InChI key

XPRDUGXOWVXZLL-UHFFFAOYSA-N

Biochem/physiol Actions

Orally active, potent dihydroorotate dehydrogenase (DHODH) inhibitor in cultures and in vivo.
Vidofludimus (4SC-101) is an orally active, potent dihydroorotate dehydrogenase (DHODH) inhibitor (human DHODH IC50 = 134 nM; IC50 = 13 µM against PHA-stimulated lymphocytes proliferation) that inhibits PHA-induced IL-17 secretion from human PBMCs (IC50 = 6 µM) and exhibits therapeutic efficacy in murine models of colitis (50-100 mg/kg/d via intragastric administration; chronic dextran sodium sulfate-induced and acute TNBS-induced colitis) and a rat model of renal transplantation in vivo (20 mg/kg/d p.o.).

Pictograms

Exclamation markEnvironment

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Onkar P Kulkarni et al.
The American journal of pathology, 176(6), 2840-2847 (2010-04-24)
Immunosuppressive treatments of systemic lupus (SLE) remain associated with significant toxicities; hence, compounds with better toxicity profiles are needed. Dihydroorotate dehydrogenase (DHODH) inhibition with leflunomide has proven to be effective in autoimmune diseases including SLE, but leflunomide can cause a
Leo R Fitzpatrick et al.
Inflammatory bowel diseases, 16(10), 1763-1777 (2010-03-24)
Dihydroorotate dehydrogenase (DHODH) is a key enzyme involved in pyrimidine biosynthesis. DHODH is a known target for the treatment of autoimmune diseases. 4SC-101 is a novel immunosuppressive drug that inhibits DHODH. A goal of our study was to examine the
Krisztina Rusai et al.
Transplantation, 93(11), 1101-1107 (2012-05-23)
4SC-101 is a novel dihydroorotate dehydrogenase inhibitor and a blocker of interleukin (IL)-17 secretion with beneficial effects in experimental lupus and inflammatory bowel disease. Its immunomodulatory effect on acute kidney rejection is not known; therefore, in this study, the impact

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