3-{2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl}-1,2,3,4-tetrahydroquinazoline-2,4-dione

• ChemBase ID: 73086
• Molecular Formular: C22H22FN3O3
• Molecular Mass: 395.4267832
• Monoisotopic Mass: 395.1645198
• SMILES: c1ccc2c(c1)c(=O)n(c(=O)[nH]2)CCN1CCC(CC1)C(=O)c1ccc(cc1)F
• Canonical SMILES: Fc1ccc(cc1)C(=O)C1CCN(CC1)CCn1c(=O)[nH]c2c(c1=O)cccc2
• InChI: InChI=1S/C22H22FN3O3/c23-17-7-5-15(6-8-17)20(27)16-9-11-25(12-10-16)13-14-26-21(28)18-3-1-2-4-19(18)24-22(26)29/h1-8,16H,9-14H2,(H,24,29)
• InChIKey: FPCCSQOGAWCVBH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl}-1,2,3,4-tetrahydroquinazoline-2,4-dione
• IUPAC Traditional name: 3-{2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl}-1H-quinazoline-2,4-dione; ketanserin
• Synonyms: R 41468; Vulketan Gel; Ketanserin (Vulketan Gel); 3-[2-[4-(4-Fluorobenzoyl)-1-piperidinyl]ethyl]-2,4(1H,3H)-quinazolinedione; Ketensin; Ketanserin

Database IDs

• CAS Number: 74050-98-9
• PubChem SID: 162038006
• PubChem CID: 3822

CALCULATED PROPERTIES

• Acid pKa: 11.424021
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.8247793
• LogD (pH = 7.4): 3.361728
• Log P: 3.6093197
• Molar Refractivity: 109.1073 cm^3
• Polarizability: 40.334778 Å^3
• Polar Surface Area: 69.72 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: Off-White Solid
• Melting Point: 230-232°C

Safety Information

• Storage Condition: -20°C; Refrigerator

Pharmacology Properties

• Target: 5-HT

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2232

Research Area: Cancer
Biological Activity:
Ketanserin (Vulketan Gel) is specific 5-HT2A serotonin receptor antagonist with a Ki of 2.5 nM for rat and human 5-HT2A. Ketanserin (Vulketan Gel) is a drug with affinity for multiple G protein-coupled receptors. Ketanserin ( Vulketan Gel) inhibits rat and human 5-HT2C with Ki of 50 and100 nM, respectively and has higher affinity binding for alpha-1 adrenergic (Ki = ~ 40 nM) and Histamine H1 (Ki = 2 nM). Ketanserin (Vulketan Gel) can also be used to discriminate between 5-HT1D and 5-HT1B receptor subtypes. Ketanserin (Vulketan Gel) has antihypertensive properties. Ketanserin (Vulketan Gel) also reduces platelet aggregation produced by serotonin. Ketanserin also has high affinity for alpha-1 adrenergic receptors, and very high affinity for histamine H1 receptors. Ketanserin (Vulketan Gel) was shown to reduce the severity and frequency of the vasospasm in Raynaud’s phenomenon. [1][2][3]References on Ketanserin (Vulketan Gel)[1] http://en.wikipedia.org/wiki/Ketanserin, , [2] Neurochem Int., 1995 Dec, 27(6):489-96.[3] Eur J Pharmacol., 1991 Jan 25, 206(1):39-45.

Toronto Research Chemicals - K165450

An antihypertensive, with affinity for multiple GPCR receptors.

REFERENCES

• Rego AC et al. Neurochem Int. 1995 Dec; 27(6):489-96.
• Zhu, Y., et al.: Biol. Pharm. Bull., 32, 1173 (2009)
• Shen, K., et al.: J. Pharm. Pharmacol., 61, 517 (2009)
• Brea, J., et al.: Mol. Pharmacol., 75, 1380 (2009)
• Varma, M., et al.: J. Med. Chem., 52, 4844 (2009)