3-(cyclopentyloxy)-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide

• ChemBase ID: 1562
• Molecular Formular: C18H18Cl2N2O3
• Molecular Mass: 381.25312
• Monoisotopic Mass: 380.06944781
• SMILES: Clc1cncc(Cl)c1NC(=O)c1ccc(OC)c(c1)OC1CCCC1
• Canonical SMILES: COc1ccc(cc1OC1CCCC1)C(=O)Nc1c(Cl)cncc1Cl
• InChI: InChI=1S/C18H18Cl2N2O3/c1-24-15-7-6-11(8-16(15)25-12-4-2-3-5-12)18(23)22-17-13(19)9-21-10-14(17)20/h6-10,12H,2-5H2,1H3,(H,21,22,23)
• InChIKey: RRRUXBQSQLKHEL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(cyclopentyloxy)-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide
• IUPAC Traditional name: piclamilast
• Synonyms: RP 73-401; Piclamilast

Database IDs

• CAS Number: 144035-83-6
• PubChem SID: 46508612; 160965019
• PubChem CID: 154575
• CHEMBL: 42126
• Chemspider ID: 136184
• DrugBank ID: EXPT02600
• KEGG ID: D05474
• Unique Ingredient Identifier: WM58D7C3ZT
• Wikipedia Title: Piclamilast

CALCULATED PROPERTIES

ALOGPS 2.1

• Solubility (Water): 6.10e-03 g/l
• Log P: 4.65
• LOG S: -4.8

JChem

• Acid pKa: 8.248247
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.093809
• LogD (pH = 7.4): 4.040309
• Log P: 4.094907
• Molar Refractivity: 98.3838 cm^3
• Polarizability: 37.571217 Å^3
• Polar Surface Area: 60.45 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

DrugBank - DB01791

• Drug Groups: experimental
• Description: Piclamilast (RP-73,401), is a selective PDE4 inhibitor. It is comparable to other PDE4 inhibitors for its anti-inflammatory effects. It has been investigated for its applications to the treatment of conditions such as chronic obstructive pulmonary disease, bronchopulmonary dysplasia and asthma. It is a second generation compound that exhibits structural functionalities of the PDE4 inhibitors cilomilast and roflumilast. The structure for piclamilast was first elucidated in a 1995 European patent application.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia