Cidoxepin

Pharmaceutical drug
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
  • 3607-18-9
PubChem CID
  • 667468
ChemSpider
  • 580850
UNII
  • F96TTB8728
ChEBI
  • CHEBI:36691
Chemical and physical data
FormulaC19H21NO
Molar mass279.383 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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.[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. doi:10.1177/009127006900900109. PMID 4885966. S2CID 40022213.
  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.

External links

  • Cidoxepin - AdisInsight


  • v
  • t
  • e
SSRIsTooltip Selective serotonin reuptake inhibitors
SNRIsTooltip Serotonin–norepinephrine reuptake inhibitors
NRIsTooltip Norepinephrine reuptake inhibitors
NDRIsTooltip Norepinephrine–dopamine reuptake inhibitors
NaSSAsTooltip Noradrenergic and specific serotonergic antidepressants
SARIsTooltip Serotonin antagonist and reuptake inhibitors
SMSTooltip Serotonin modulator and stimulators
Others
TCAsTooltip Tricyclic antidepressants
TeCAsTooltip Tetracyclic antidepressants
Others
Non-selective
MAOATooltip Monoamine oxidase A-selective
MAOBTooltip Monoamine oxidase B-selective
Miscellaneous
  • v
  • t
  • e
Benzimidazoles (*)
Diarylmethanes
Ethylenediamines
Tricyclics
Others
For topical use
  • v
  • t
  • e
mAChRsTooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(and prodrugs)
See also
Receptor/signaling modulators
Nicotinic acetylcholine receptor modulators
Acetylcholine metabolism/transport modulators
  • v
  • t
  • e
nAChRsTooltip Nicotinic acetylcholine receptors
Agonists
(and PAMsTooltip positive allosteric modulators)
Antagonists
(and NAMsTooltip negative allosteric modulators)
Precursors
(and prodrugs)
See also
Receptor/signaling modulators
Muscarinic acetylcholine receptor modulators
Acetylcholine metabolism/transport modulators
  • v
  • t
  • e
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
  • See also: Receptor/signaling modulators
  • Dopaminergics
  • Serotonergics
  • Monoamine reuptake inhibitors
  • Monoamine releasing agents
  • Monoamine metabolism modulators
  • Monoamine neurotoxins
  • v
  • t
  • e
H1
Agonists
Antagonists
  • Unknown/unsorted: Azanator
  • Belarizine
  • Elbanizine
  • Flotrenizine
  • GSK1004723
  • Napactadine
  • Tagorizine
  • Trelnarizine
  • Trenizine
H2
Agonists
Antagonists
H3
Agonists
Antagonists
H4
Agonists
Antagonists
See also
Receptor/signaling modulators
Monoamine metabolism modulators
Monoamine reuptake inhibitors
  • v
  • t
  • e
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
  • See also: Receptor/signaling modulators
  • Adrenergics
  • Dopaminergics
  • Melatonergics
  • Monoamine reuptake inhibitors and releasing agents
  • Monoamine metabolism modulators
  • Monoamine neurotoxins
  • v
  • t
  • e
Classes
Antidepressants
(Tricyclic antidepressants (TCAs))
Antihistamines
Antipsychotics
Anticonvulsants
Anticholinergics
Others


Stub icon

This drug article relating to the nervous system is a stub. You can help Wikipedia by expanding it.

  • v
  • t
  • e
Stub icon

This dermatologic drug article is a stub. You can help Wikipedia by expanding it.

  • v
  • t
  • e