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Also known as: Cevidoplenib [inn], 1703788-21-9, 3n3h8bx897, Cyclopropyl-[5-[[4-[4-[[(4s)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-1-methylindol-3-yl]methanone, Methanone, cyclopropyl(5-((4-(4-(((4s)-4-hydroxy-2-isoxazolidinyl)methyl)-3-methyl-1h-pyrazol-1-yl)-2-pyrimidinyl)amino)-1-methyl-1h-indol-3-yl)-, Cevidoplenib [who-dd]

Molecular Formula

C₂₅H₂₇N₇O₃

Molecular Weight

473.5 g/mol

InChI Key

YCZUBLQESBVOSH-IBGZPJMESA-N

FDA UNII

3N3H8BX897

Cevidoplenib is an orally available inhibitor of spleen tyrosine kinase (SYK), with potential anti-inflammatory and immunomodulating activities. Upon oral administration, cevidoplenib binds to and inhibits the activity of SYK, blocking Fc receptor and B-cell receptor (BCR)-mediated signaling in inflammatory cells, including macrophages, neutrophils, mast cells, natural killer (NK) cells and B-cells. This leads to the inhibition of the activation of these inflammatory cells, and the related inflammatory responses and tissue damage. SYK, a non-receptor cytoplasmic protein tyrosine kinase widely expressed in hematopoietic cells, plays a key role in Fc receptor and B-cell receptor signaling in inflammatory cells. It is involved in coupling activated immunoreceptors, such as Fc receptors and B-cell receptors, to signal downstream events that mediate diverse cellular responses, including proliferation, differentiation, and phagocytosis, which are important for allergic and antibody-mediated immune diseases such as immune thrombocytopenia (ITP).

1 2D Structure

Cevidoplenib

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

cyclopropyl-[5-[[4-[4-[[(4S)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-1-methylindol-3-yl]methanone

2.1.2 InChI

InChI=1S/C25H27N7O3/c1-15-17(10-31-12-19(33)14-35-31)11-32(29-15)23-7-8-26-25(28-23)27-18-5-6-22-20(9-18)21(13-30(22)2)24(34)16-3-4-16/h5-9,11,13,16,19,33H,3-4,10,12,14H2,1-2H3,(H,26,27,28)/t19-/m0/s1

2.1.3 InChI Key

YCZUBLQESBVOSH-IBGZPJMESA-N

2.1.4 Canonical SMILES

CC1=NN(C=C1CN2CC(CO2)O)C3=NC(=NC=C3)NC4=CC5=C(C=C4)N(C=C5C(=O)C6CC6)C

2.1.5 Isomeric SMILES

CC1=NN(C=C1CN2C[C@@H](CO2)O)C3=NC(=NC=C3)NC4=CC5=C(C=C4)N(C=C5C(=O)C6CC6)C

2.2 Other Identifiers

2.2.1 UNII

3N3H8BX897

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Cevidoplenib [inn]

2. 1703788-21-9

3. 3n3h8bx897

4. Cyclopropyl-[5-[[4-[4-[[(4s)-4-hydroxy-1,2-oxazolidin-2-yl]methyl]-3-methylpyrazol-1-yl]pyrimidin-2-yl]amino]-1-methylindol-3-yl]methanone

5. Methanone, Cyclopropyl(5-((4-(4-(((4s)-4-hydroxy-2-isoxazolidinyl)methyl)-3-methyl-1h-pyrazol-1-yl)-2-pyrimidinyl)amino)-1-methyl-1h-indol-3-yl)-

6. Cevidoplenib [who-dd]

7. Unii-3n3h8bx897

8. Chembl3921923

9. Schembl16653204

10. Bdbm196772

11. Ex-a5914

12. Hy-109082

13. Cs-0039259

14. Us9212178, 1

15. (s)-cyclopropyl(5-(4-(4-((4-hydroxyisoxazolidin-2-yl)methyl)-3-methyl-1h-pyrazol-1-yl)pyrimidin-2-ylamino)-1-methyl-1h-indol-3-yl)methanone

2.4 Create Date

2015-05-04

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₂₇N₇O₃
Molecular Weight	473.5 g/mol
XLogP3	2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	7
Exact Mass	g/mol
Monoisotopic Mass	g/mol
Topological Polar Surface Area	110
Heavy Atom Count	35
Formal Charge	0
Complexity	769
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1