5-{N-[dihydroxy(2H5)propyl]acetamido}-1-N,3-N-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide

• ChemBase ID: 172368
• Molecular Formular: C19H26I3N3O9
• Molecular Mass: 821.13785
• Monoisotopic Mass: 820.88032343
• SMILES: c1(c(c(c(c(c1I)C(=O)NCC(O)CO)I)N(CC(CO)O)C(=O)C)I)C(=O)NCC(CO)O
• Canonical SMILES: OCC(CN(c1c(I)c(C(=O)NCC(CO)O)c(c(c1I)C(=O)NCC(CO)O)I)C(=O)C)O
• InChI: InChI=1S/C19H26I3N3O9/c1-8(29)25(4-11(32)7-28)17-15(21)12(18(33)23-2-9(30)5-26)14(20)13(16(17)22)19(34)24-3-10(31)6-27/h9-11,26-28,30-32H,2-7H2,1H3,(H,23,33)(H,24,34)
• InChIKey: NTHXOOBQLCIOLC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-{N-[dihydroxy(^2H₅)propyl]acetamido}-1-N,3-N-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide
• IUPAC Traditional name: 5-{N-[dihydroxy(^2H₅)propyl]acetamido}-1-N,3-N-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide
• Synonyms: 2-[(1S)-1-(2,6-Dichlorophenoxy)ethyl]-4,5-dihydro-1H-imidazole; (+)-Lofexidine; Dexlofexidine; (S)-Lofexidine

Database IDs

• CAS Number: 81447-79-2
• PubChem SID: 164228278
• PubChem CID: 46782072

CALCULATED PROPERTIES

• Acid pKa: 11.731379
• H Acceptors: 9
• H Donor: 8
• LogD (pH = 5.5): -1.9508227
• LogD (pH = 7.4): -1.9508405
• Log P: -1.9508225
• Molar Refractivity: 148.839 cm^3
• Polarizability: 57.8173 Å^3
• Polar Surface Area: 199.89 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L469400

The S-enantiomer of Lofexidine. α2-Adrenoceptor agonist related structurally to Clonidine. Used in treatment of opioid withdrawal symptoms; antihypertensive.

REFERENCES

• Velly, J., et al.: J. Pharmacol., 8, 351 (1977)
• Jarrot, B., et al.: Biochem. Pharmacol., 28, 141 (1977)
• Birch, P., at al.: Brit. J. Pharmacol., 68, 107 (1977)