3-(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide

• ChemBase ID: 72846
• Molecular Formular: C17H14Cl2F2N2O3
• Molecular Mass: 403.2074664
• Monoisotopic Mass: 402.03495412
• SMILES: n1cc(c(c(c1)Cl)NC(=O)c1ccc(c(c1)OCC1CC1)OC(F)F)Cl
• Canonical SMILES: FC(Oc1ccc(cc1OCC1CC1)C(=O)Nc1c(Cl)cncc1Cl)F
• InChI: InChI=1S/C17H14Cl2F2N2O3/c18-11-6-22-7-12(19)15(11)23-16(24)10-3-4-13(26-17(20)21)14(5-10)25-8-9-1-2-9/h3-7,9,17H,1-2,8H2,(H,22,23,24)
• InChIKey: MNDBXUUTURYVHR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide
• IUPAC Traditional name: 3-(cyclopropylmethoxy)-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide; roflumilast
• Synonyms: Daxas; Roflumilast; 3-(Cyclopropylmethoxy)-N-(3,5-dichloro-4-pyridinyl)-4-(difluoromethoxy)benzamide; B 9302-107; BY 217; BYK 20869

Database IDs

• CAS Number: 162401-32-3
• PubChem SID: 162037767
• PubChem CID: 449193

CALCULATED PROPERTIES

• Acid pKa: 8.182302
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.4463134
• LogD (pH = 7.4): 4.384677
• Log P: 4.4475408
• Molar Refractivity: 93.9215 cm^3
• Polarizability: 35.35955 Å^3
• Polar Surface Area: 60.45 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chlorform; DMSO
• Apperance: White to Off-White Solid
• Melting Point: 154-158°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2131

Research Area: Metabolic Disease
Biological Activity:
Roflumilast(Daxas) is a selective, long-acting the enzyme PDE-4 inhibitor with an IC50 of 0.8 nM. [1] It has antiinflammatory effects and is under development as an orally administered drug for the treatment of inflammatory conditions of the lungs such as asthma, and chronic obstructive pulmonary disease. While roflumilast was found to be effective in clinical trials, it produced several dose-limiting side effects including nausea, diarrhoea and headache, and development is continuing in an attempt to minimise the incidence of side effects while retaining clinical efficacy. [2][3]

Toronto Research Chemicals - R639700

Selective phosphodiesterase 4(PDE4) inhibitor. Antiasthmatic; in treatment of chronic obstructive pulmonary disease.

REFERENCES

• http://en.wikipedia.org/wiki/Roflumilast
• Hatzelmann, A., et al.: J. Pharmacol. Exp. Ther., 297, 267 (2001)
• Schmidt, B.M.W., et al.: J. Allergy Clin. Immunol., 108, 530 (2001)
• Timmer, W., et al.: J. Clin. Pharmacol., 42, 297 (2001)
• Rabe, K.F., et al.: Lancet, 366, 563 (2001)