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Also known as: Paltusotine [inn], F2ibd1gmd3, 2172870-89-0, 3-(4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl)-2-hydroxybenzonitrile, Benzonitrile, 3-(4-(4-amino-1-piperidinyl)-3-(3,5-difluorophenyl)-6-quinolinyl)-2-hydroxy-, 3-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-2-hydroxybenzonitrile

Molecular Formula

C₂₇H₂₂F₂N₄O

Molecular Weight

456.5 g/mol

InChI Key

GHILNKWBALQPDP-UHFFFAOYSA-N

FDA UNII

F2IBD1GMD3

Paltusotine is an orally bioavailable, nonpeptide somatostatin receptor type 2 (SST2; SSTR2) agonist, with potential growth hormone (GH) secretion-inhibiting and antineoplastic activities. Upon oral administration, paltusotine targets, binds to and activates SSTR2, which leads to an inhibition in the secretion of human growth hormone (hGH) in the pituitary gland and results in decreased production of insulin-like growth factor (IGF-1). This may inhibit IGF-1-mediated cell signaling pathways, and lead to apoptosis. SSTR2 is overexpressed by some neuroendocrine tumor cells, and GH is over-produced in the pituitary gland in acromegaly.

1 2D Structure

Paltusotine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-2-hydroxybenzonitrile

2.1.2 InChI

InChI=1S/C27H22F2N4O/c28-19-10-18(11-20(29)13-19)24-15-32-25-5-4-16(22-3-1-2-17(14-30)27(22)34)12-23(25)26(24)33-8-6-21(31)7-9-33/h1-5,10-13,15,21,34H,6-9,31H2

2.1.3 InChI Key

GHILNKWBALQPDP-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CN(CCC1N)C2=C3C=C(C=CC3=NC=C2C4=CC(=CC(=C4)F)F)C5=CC=CC(=C5O)C#N

2.2 Other Identifiers

2.2.1 UNII

F2IBD1GMD3

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Paltusotine [inn]

2. F2ibd1gmd3

3. 2172870-89-0

4. 3-(4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl)-2-hydroxybenzonitrile

5. Benzonitrile, 3-(4-(4-amino-1-piperidinyl)-3-(3,5-difluorophenyl)-6-quinolinyl)-2-hydroxy-

6. 3-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-2-hydroxybenzonitrile

7. Unii-f2ibd1gmd3

8. Schembl19769109

9. Bdbm405588

10. Crn-00808

11. Us10351547, Compound 2-2

12. Hy-109155

13. Cs-0116068

2.4 Create Date

2018-06-23

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₂₂F₂N₄O
Molecular Weight	456.5 g/mol
XLogP3	5.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	3
Exact Mass	456.17616766 g/mol
Monoisotopic Mass	456.17616766 g/mol
Topological Polar Surface Area	86.2 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	727
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	1