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Chemistry

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Also known as: Fw5vy7926x, 1-cyclopentene-1-carboxylic acid, 2-(((3-fluoro-3'-methoxy(1,1'-biphenyl)-4-yl)amino)carbonyl)-, calcium salt (2:1), 1354012-90-0, Unii-fw5vy7926x, Vidofludimus calcium [who-dd]

Molecular Formula

C₄₀H₃₄CaF₂N₂O₈

Molecular Weight

748.8 g/mol

InChI Key

KWSJBFAXOPFZSO-UHFFFAOYSA-L

FDA UNII

FW5VY7926X

Vidofludimus Calcium Anhydrous is the calcium salt form of vidofludimus, an orally bioavailable inhibitor of dihydroorotate dehydrogenase (DHODH), with potential anti-inflammatory, immunomodulating and anti-viral activities. Upon administration, vidofludimus specifically targets, binds to and prevents the activation of DHODH. This prevents the fourth enzymatic step in de novo pyrimidine synthesis, leading to inhibition of transcriptional elongation, cell cycle arrest, and apoptosis in activated lymphocytes. DHODH inhibition also leads to metabolic stress in activated lymphocytes and inhibition of the release of proinflammatory cytokines including interleukin (IL)-17 (IL-17A and IL-17F) and interferon-gamma (IFNg), thereby reducing inflammation. In addition, DHODH inhibition may lead to host-based anti-viral activity against many viruses. DHODH, a mitochondrial enzyme that catalyzes the conversion of dihydroorotate (DHO) to orotate, is a key enzyme in pyrimidine de novo biosynthesis. Metabolically highly activated and rapidly proliferating lymphocytes and various virus infected cells require de novo synthesis to meet their needs for pyrimidines.

1 2D Structure

Vidofludimus calcium anhydrous

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

calcium;2-[[2-fluoro-4-(3-methoxyphenyl)phenyl]carbamoyl]cyclopentene-1-carboxylate

2.1.2 InChI

InChI=1S/2C20H18FNO4.Ca/c2*1-26-14-5-2-4-12(10-14)13-8-9-18(17(21)11-13)22-19(23)15-6-3-7-16(15)20(24)25;/h2*2,4-5,8-11H,3,6-7H2,1H3,(H,22,23)(H,24,25);/q;;+2/p-2

2.1.3 InChI Key

KWSJBFAXOPFZSO-UHFFFAOYSA-L

2.1.4 Canonical SMILES

COC1=CC=CC(=C1)C2=CC(=C(C=C2)NC(=O)C3=C(CCC3)C(=O)[O-])F.COC1=CC=CC(=C1)C2=CC(=C(C=C2)NC(=O)C3=C(CCC3)C(=O)[O-])F.[Ca+2]

2.2 Other Identifiers

2.2.1 UNII

FW5VY7926X

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Fw5vy7926x

2. 1-cyclopentene-1-carboxylic Acid, 2-(((3-fluoro-3'-methoxy(1,1'-biphenyl)-4-yl)amino)carbonyl)-, Calcium Salt (2:1)

3. 1354012-90-0

4. Unii-fw5vy7926x

5. Vidofludimus Calcium [who-dd]

2.4 Create Date

2012-04-23

3 Chemical and Physical Properties

Molecular Formula	C₄₀H₃₄CaF₂N₂O₈
Molecular Weight	748.8 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	8
Exact Mass	748.1909132 g/mol
Monoisotopic Mass	748.1909132 g/mol
Topological Polar Surface Area	157 Å²
Heavy Atom Count	53
Formal Charge	0
Complexity	571
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3