166037-77-0

Basic information

• Product Name: 5-Isobenzofurancarbonitrile, 1-(3-aminopropyl)-1-(4-fluorophenyl)-1,3-dihydro-, (1R)-
• CAS NO: 166037-77-0
• Molecular Formula: C18H17FN2O
• Molecular Weight: 296.344
• Mol File: 166037-77-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5-Isobenzofurancarbonitrile, 1-(3-aminopropyl)-1-(4-fluorophenyl)-1,3-dihydro-, (1R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Isobenzofurancarbonitrile, 1-(3-aminopropyl)-1-(4-fluorophenyl)-1,3-dihydro-, (1R)-(166037-77-0)
• EPA Substance Registry System: 5-Isobenzofurancarbonitrile, 1-(3-aminopropyl)-1-(4-fluorophenyl)-1,3-dihydro-, (1R)-(166037-77-0)

Safety Data

• Hazardous Substances Data: 166037-77-0(Hazardous Substances Data)

Upstream product

• 62498-69-5 didesmethylcitalopram 
• 144010-85-5 (-)-Desmethylcitalopram 

Downstream Products

• 128196-02-1 (S)-1-[3-(dimethylamino)propyl]-1-(4-flouorphenyl)-1,3-dihydro-5-isobenzofuran carbonitrile 

Relevant articles and documents

Studies on the stereoselective metabolism of citalopram by human liver microsomes and cDNA-expressed cytochrome P450 enzymes

The involvement of CYP enzymes in the metabolism of citalopram was studied, inclusive the conversion of demethylcitalopram to didemethylcitalopram and the formation of citalopram N-oxide, which both have not been considered previously. Using human mixed liver microsomes and cDNA-expressed CYP enzymes, we confirmed that CYP3A4, 2C19 and 2D6 are involved in the first demethylation step of citalopram, all favouring conversion of the biologically active S-enantiomer. Inhibitor studies indicated that at therapeutic citalopram concentrations CYP3A4 was responsible for 40-50% of demethylcitalopram formation, while the contribution of CYP2C19 increased and that of CYP2D6 tended to decrease with increasing drug concentration, CYP2D6 exclusively mediated the second demethylation step, and citalopram N-oxide was also exclusively formed by CYP2D6. None of the studied CYP enzymes mediated deamination to the propionic acid derivative.

Treatment or prophylaxis of migraine or headache disorders using citalopram, escitalopram or citalopram metabolites

Methods for prophylaxis of or treating or preventing migraine or migraine headaches, or other headache disorders include administering to a subject in need of treatment a therapeutically effective amount of citalopram, escitalopram, or a racemic or optically pure citalopram metabolite, or pharmaceutically acceptable salts, solvates, polymorphs, or hydrates thereof.