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Cidoxepin

Clinical data
Other names	(Z)-Doxepin; cis-Doxepin; P-4599
Identifiers
IUPAC name (3Z)-3-(6H-Benzobenzoxepin-11-ylidene)-N,N-dimethylpropan-1-amine
CAS Number	3607-18-9
PubChem CID	667468
ChemSpider	580850
UNII	F96TTB8728
ChEBI	CHEBI:36691
CompTox Dashboard (EPA)	DTXSID301318253
Chemical and physical data
Formula	C19H21NO
Molar mass	279.383 g·mol
3D model (JSmol)	Interactive image
SMILES CN(C)CC/C=C\1/C2=CC=CC=C2COC3=CC=CC=C31
InChI 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. 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. 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. The central anticholinergic activity of cidoxepin has been reported to be 3-fold greater than that of the trans isomer in mice.

Cidoxepin has recently been reinvestigated and is now currently under development as an antihistamine by Elorac, Inc. for the treatment of chronic urticaria (hives). As of 2017, it is in phase II clinical trials for this indication. 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.

See also

• Esmirtazapine
• Nordoxepin

References

1. ^ 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. doi:10.1177/009127006900900109. PMID 4885966. S2CID 40022213.
3. ^ Shufeng Zhou (6 April 2016). Cytochrome P450 2D6: Structure, Function, Regulation and Polymorphism. CRC Press. pp. 142–. ISBN 978-1-4665-9788-4.
4. ^ "Cidoxepin - AdisInsight".
5. ^ 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.

External links

• Cidoxepin - AdisInsight

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• Dimethylamino compounds
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