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Glasdegib Maleate

Glasdegib Maleate

Synopsis, Chemistry

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Also known as: 2030410-25-2, Pf-04449913 maleate, Daurismo, Th2ev99s4z, 2030410-25-2 (maleate), 1-((2r,4r)-2-(1h-benzo[d]imidazol-2-yl)-1-methylpiperidin-4-yl)-3-(4-cyanophenyl)urea maleate

Molecular Formula

C₂₅H₂₆N₆O₅

Molecular Weight

490.5 g/mol

InChI Key

VJCVKWFBWAVYOC-UIXXXISESA-N

FDA UNII

TH2EV99S4Z

Glasdegib Maleate is the maleate salt form of glasdegib, an orally bioavailable small-molecule, smoothened (SMO) receptor inhibitor, with potential antineoplastic activity. Upon oral administration, glasdegib targets, binds to and inhibits the activity of SMO. This inhibits the activity of the Hedgehog (Hh) signaling pathway and inhibits the growth of tumor cells in which this pathway is aberrantly activated. SMO, a transmembrane protein, is involved in Hh signal transduction. The Hh signaling pathway plays an important role in cellular growth, differentiation, repair, and cancer stem cell (CSC) survival. Constitutive activation of Hh pathway signaling has been observed in various types of malignancies and is associated with uncontrolled cellular proliferation in a variety of cancers.

1 2D Structure

Glasdegib Maleate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[(2R,4R)-2-(1H-benzimidazol-2-yl)-1-methylpiperidin-4-yl]-3-(4-cyanophenyl)urea;(Z)-but-2-enedioic acid

2.1.2 InChI

InChI=1S/C21H22N6O.C4H4O4/c1-27-11-10-16(24-21(28)23-15-8-6-14(13-22)7-9-15)12-19(27)20-25-17-4-2-3-5-18(17)26-20;5-3(6)1-2-4(7)8/h2-9,16,19H,10-12H2,1H3,(H,25,26)(H2,23,24,28);1-2H,(H,5,6)(H,7,8)/b;2-1-/t16-,19-;/m1./s1

2.1.3 InChI Key

VJCVKWFBWAVYOC-UIXXXISESA-N

2.1.4 Canonical SMILES

CN1CCC(CC1C2=NC3=CC=CC=C3N2)NC(=O)NC4=CC=C(C=C4)C#N.C(=CC(=O)O)C(=O)O

2.1.5 Isomeric SMILES

CN1CC[C@H](C[C@@H]1C2=NC3=CC=CC=C3N2)NC(=O)NC4=CC=C(C=C4)C#N.C(=C\C(=O)O)\C(=O)O

2.2 Other Identifiers

2.2.1 UNII

TH2EV99S4Z

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-(2-(1h-benzo(d)imidazol-2-yl)-1-methylpiperidin-4-yl)-3-(4-cyanophenyl)urea

2. Daurismo

3. Glasdegib

4. Pf-04449913

2.3.2 Depositor-Supplied Synonyms

1. 2030410-25-2

2. Pf-04449913 Maleate

3. Daurismo

4. Th2ev99s4z

5. 2030410-25-2 (maleate)

6. 1-((2r,4r)-2-(1h-benzo[d]imidazol-2-yl)-1-methylpiperidin-4-yl)-3-(4-cyanophenyl)urea Maleate

7. Glasdegib Maleate (jan)

8. Glasdegib Maleate [jan]

9. 1-((2r,4r)-2-(1h-benzimidazol-2-yl)-1-methylpiperidin-4-yl)-3-(4-cyanophenyl)ureamaleatesalt

10. Urea, N-((2r,4r)-2-(1h-benzimidazol-2-yl)-1-methyl-4-piperidinyl)-n'-(4-cyanophenyl)-, (2z)-2-butenedioate (1:1)

11. Pf 04449913 Maleate

12. Daurismo (tn)

13. Unii-th2ev99s4z

14. Chembl4297534

15. Schembl18171548

16. Dtxsid301027747

17. Glasdegib Maleate [who-dd]

18. Glasdegib Maleate [orange Book]

19. D11107

20. Pf-04449913 Maleate Salt, >=98% (hplc)

21. 1-((2r,4r)-2-(1h-benzimidazol-2-yl)-1-methylpiperidin-4-yl)-3-(4-cyanophenyl)urea Maleate Salt

22. 1-[(2r,4r)-2-(1h-benzimidazol-2-yl)-1-methylpiperidin-4-yl]-3-(4-cyanophenyl)urea;(z)-but-2-enedioic Acid

2.4 Create Date

2016-12-08

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₂₆N₆O₅
Molecular Weight	490.5 g/mol
Hydrogen Bond Donor Count	5
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	5
Exact Mass	490.19646795 g/mol
Monoisotopic Mass	490.19646795 g/mol
Topological Polar Surface Area	171 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	714
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Indication

Daurismo is indicated, in combination with low-dose cytarabine, for the treatment of newly diagnosed de novo or secondary acute myeloid leukaemia (AML) in adult patients who are not candidates for standard induction chemotherapy.

5 Pharmacology and Biochemistry

5.1 ATC Code

L01XX63