3-[(2,2,3,3-2H4)cyclopropylmethoxy]-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide

• ChemBase ID: 177588
• Molecular Formular: C17H14Cl2F2N2O3
• Molecular Mass: 403.2074664
• Monoisotopic Mass: 402.03495412
• SMILES: c1(c(cc(cc1)C(=O)Nc1c(cncc1Cl)Cl)OCC1CC1)OC(F)F
• 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-[(2,2,3,3-^2H₄)cyclopropylmethoxy]-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide
• IUPAC Traditional name: 3-[(2,2,3,3-^2H₄)cyclopropylmethoxy]-N-(3,5-dichloropyridin-4-yl)-4-(difluoromethoxy)benzamide
• Synonyms: 3-(Cyclopropyl-d4)methoxy-N-(3,5-dichloro-4-pyridinyl)-4-(difluoromethoxy)benzamide; B 9302-107-d4; BY 217-d4; BYK 20869-d4; Daxas-d4; Roflumilast-d4

Database IDs

• PubChem SID: 164233498
• PubChem CID: 71752096

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: 35.359554 Å^3
• Polar Surface Area: 60.45 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 156-158°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - R639702

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

REFERENCES

• 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)