Cidoxepin
Clinical data
Other names(Z)-Doxepin; cis-Doxepin; P-4599
Identifiers
  • (3Z)-3-(6H-Benzo[c][1]benzoxepin-11-ylidene)-N,N-dimethylpropan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
Chemical and physical data
FormulaC19H21NO
Molar mass279.383 g·mol−1
3D model (JSmol)
  • CN(C)CC/C=C\1/C2=CC=CC=C2COC3=CC=CC=C31
  • InChI=1S/C19H21NO/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3/b17-11-
  • Key:ODQWQRRAPPTVAG-BOPFTXTBSA-N

Cidoxepin (former developmental code name P-4599), also known as cis-doxepin or (Z)-doxepin, is a tricyclic antidepressant which was developed in the 1960s but was never marketed.[1][2] It is the cis or (Z) stereoisomer of doxepin, a mixture of (E) and (Z) isomers that is used commercially in a ratio of approximately 85:15 with cidoxepin as a relatively minor constituent.[1][3] However, the drug has similar activity to that of doxepin, acting as a serotonin–norepinephrine reuptake inhibitor, H1 receptor antagonist, and anticholinergic, and notably is thought to have more antidepressant activity than trans-doxepin.[3][4][5] The central anticholinergic activity of cidoxepin has been reported to be 3-fold greater than that of the trans isomer in mice.[5]

Cidoxepin has recently been reinvestigated and is now currently under development as an antihistamine by Elorac, Inc. for the treatment of chronic urticaria (hives).[4] As of 2017, it is in phase II clinical trials for this indication.[4] The drug was also under investigation for the treatment of allergic rhinitis (hay fever), atopic dermatitis (atopic eczema), and contact dermatitis, but development for these indications was discontinued.[4]

See also

References

  1. ^ a b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 469–. ISBN 978-1-4757-2085-3.
  2. ^ Gallant DM, Bishop MP, Guerrero-Figueroa R, Selby M, Phillips R (1969). "Doxepin versus diazepam: a controlled evaluation in 100 chronic alcoholic patients". J Clin Pharmacol J New Drugs. 9 (1): 57–65. PMID 4885966.
  3. ^ a b Shufeng Zhou (6 April 2016). Cytochrome P450 2D6: Structure, Function, Regulation and Polymorphism. CRC Press. pp. 142–. ISBN 978-1-4665-9788-4.
  4. ^ a b c d "Cidoxepin - AdisInsight".
  5. ^ a b Hagedorn HW, Meiser H, Zankl H, Schulz R (2001). "Elimination of doxepin isomers from the horse following intravenous application". J. Vet. Pharmacol. Ther. 24 (4): 283–9. doi:10.1046/j.1365-2885.2001.00345.x. PMID 11555184.