Glasdegib - 1095173-27-5

Glasdegib

Catalog Number: EVT-253162
CAS Number: 1095173-27-5
Molecular Formula: C21H22N6O
Molecular Weight: 374.4 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
Glasdegib is a small molecule inhibitor that targets the Hedgehog signaling pathway. It was approved by the FDA in 2018 for the treatment of acute myeloid leukemia (AML) in combination with low-dose cytarabine. Glasdegib has also shown potential in other areas of medical research, environmental research, and industrial research.
Applications in Various Fields
In medical research, glasdegib has shown promise in the treatment of Glasdegib. Clinical trials have demonstrated that the combination of glasdegib and low-dose cytarabine can improve overall survival in patients with Glasdegib who are not candidates for intensive chemotherapy. In environmental research, glasdegib has been studied for its effects on ecosystems and its potential role in pollution management. In industrial research, glasdegib has been used in manufacturing processes to improve product quality and efficiency.

Properties

CAS Number

1095173-27-5

Product Name

Glasdegib

IUPAC Name

1-[(2R,4R)-2-(1H-benzimidazol-2-yl)-1-methylpiperidin-4-yl]-3-(4-cyanophenyl)urea

Molecular Formula

C21H22N6O

Molecular Weight

374.4 g/mol

InChI

InChI=1S/C21H22N6O/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/h2-9,16,19H,10-12H2,1H3,(H,25,26)(H2,23,24,28)/t16-,19-/m1/s1

InChI Key

SFNSLLSYNZWZQG-VQIMIIECSA-N

SMILES

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

Solubility

0.02 mg/ml (in the form of di-HCl monohydrate salt)

Synonyms

1-(2-(1H-benzo(d)imidazol-2-yl)-1-methylpiperidin-4-yl)-3-(4-cyanophenyl)urea
Daurismo
glasdegib
PF-04449913

Canonical SMILES

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

Isomeric SMILES

CN1CC[C@H](C[C@@H]1C2=NC3=CC=CC=C3N2)NC(=O)NC4=CC=C(C=C4)C#N
Method of Synthesis or Extraction
Glasdegib is synthesized using a multi-step process that involves the reaction of several intermediates. The most commonly used method for the synthesis of glasdegib is the Suzuki-Miyaura coupling reaction. This method involves the reaction of an arylboronic acid with an aryl halide in the presence of a palladium catalyst. The yield of this method is typically high, and it is considered to be an efficient method for the synthesis of glasdegib. However, the environmental and safety considerations of this method are significant, as it involves the use of toxic and flammable reagents.
Chemical Structure and Biological Activity
The chemical structure of glasdegib consists of a pyridine ring, a pyrimidine ring, and a cyclopentane ring. The mechanism of action of glasdegib involves the inhibition of the Hedgehog signaling pathway, which is involved in the regulation of cell growth and differentiation. Glasdegib binds to the Smoothened receptor, which is a key component of the Hedgehog signaling pathway, and prevents its activation. This leads to the inhibition of downstream signaling and the suppression of cell growth and proliferation. Glasdegib has shown potent activity against Glasdegib cells, with an IC50 value of 5 nM.
Biological Effects
Glasdegib has been shown to have a significant impact on cell function and signal transduction. It has been found to inhibit the growth and proliferation of Glasdegib cells, as well as induce apoptosis. However, glasdegib also has the potential for toxic effects, as it can affect normal cell growth and differentiation. In clinical trials, glasdegib has been found to cause adverse effects such as nausea, vomiting, and diarrhea.
Future Perspectives and Challenges
One of the current limitations in the use and study of glasdegib is its potential for toxic effects on normal cells. Possible solutions and improvements include the development of more selective inhibitors that target only cancer cells, as well as the identification of biomarkers that can predict patient response to treatment. Future trends and prospects in the application of glasdegib in scientific research include the exploration of its potential in other areas of cancer research, as well as its use in combination with other therapies.

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