Nordoxepin

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Nordoxepin
Clinical data
Other namesN-Desmethyldoxepin; Desmethyldoxepin; Demethyldoxepin; Monodesmethyldoxepin
Pharmacokinetic data
Elimination half-life31 hours[1]
Identifiers
  • (E/Z)-3-(Dibenzo[b,e]oxepin-11(6H)-ylidene)-N-methylpropan-1-amine
JSmol)
  • CNCCC=C1C2=CC=CC=C2COC3=CC=CC=C31
  • InChI=1S/C18H19NO/c1-19-12-6-10-16-15-8-3-2-7-14(15)13-20-18-11-5-4-9-17(16)18/h2-5,7-11,19H,6,12-13H2,1H3
  • Key:HVKCEFHNSNZIHO-UHFFFAOYSA-N

Nordoxepin, also known as N-desmethyldoxepin, is an organic compound. A colorless solid, it attracted attention as the major active metabolite of the tricyclic antidepressant (TCA) doxepin (Sinequan).[2] It has been found to play a significant role in the antidepressant effects of doxepin.[3]

Nordoxepin is a

pharmaceutical doxepin is supplied in an approximate 85:15 ratio mixture of (E)- and (Z)-stereoisomers and plasma concentrations of doxepin remain roughly the same as this ratio with treatment, plasma levels of the (E)- and (Z)-stereoisomers of nordoxepin, due to stereoselective metabolism of doxepin by cytochrome P450 enzymes, are approximately 1:1.[2]

Nordoxepin is

antiadrenergic, antihistamine, and anticholinergic activities.[5][6][7]

Nordoxepin is formed from doxepin mainly by

elimination half-life of nordoxepin is approximately 31 hours, which is almost twice that of doxepin (mean 17 hours).[1]

See also

References

  1. ^ a b "Sinepin Capsules 25mg - Summary of Product Characteristics (SPC)". electronic Medicines Compendium. Marlborough Pharmaceuticals Ltd. 22 September 2011. Retrieved 3 December 2013.
  2. ^
    ISBN 978-1-60913-345-0
    .
  3. ^
    S2CID 41765748
    .
  4. S2CID 26739281
    .
  5. ^
    ISBN 978-0-471-95052-3
    .
  6. ^
    ISBN 978-3-527-64632-6
    .
  7. ISBN 978-1-58562-309-9
    .
  8. S2CID 8089917
    .