Cidoxepin (former developmental code name P-4599), also known as ''cis''-doxepin or (''Z'')-doxepin, is a
tricyclic antidepressant
Tricyclic antidepressants (TCAs) are a class of medications that are used primarily as antidepressants, which is important for the management of depression. They are second-line drugs next to SSRIs. TCAs were discovered in the early 1950s and wer ...
which was developed in the 1960s but was never marketed.
It is the ''cis'' or (''Z'')
stereoisomer
In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...
of
doxepin
Doxepin is a medication falling in the tricyclic antidepressant (TCA) class used to treat major depressive disorder, anxiety disorders, chronic hives, and insomnia. For label updates seFDA index page for NDA 022036/ref> For hives it is a less ...
, 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
Serotonin–norepinephrine reuptake inhibitors (SNRIs) are a class of antidepressant drugs used to treat major depressive disorder (MDD), anxiety disorders, obsessive–compulsive disorder (OCD), social phobia, attention-deficit hyperactivity di ...
,
H1 receptor antagonist, and
anticholinergic
Anticholinergics (anticholinergic agents) are substances that block the action of the neurotransmitter called acetylcholine (ACh) at synapses in the central and peripheral nervous system.
These agents inhibit the parasympathetic nervous sys ...
, 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
Antihistamines are drugs which treat allergic rhinitis, common cold, influenza, and other allergies. Typically, people take antihistamines as an inexpensive, generic (not patented) drug that can be bought without a prescription and provid ...
by Elorac, Inc. for the treatment of chronic
urticaria
Hives, also known as urticaria, is a kind of skin rash with red, raised, itchy bumps. Hives may burn or sting. The patches of rash may appear on different body parts, with variable duration from minutes to days, and does not leave any long-last ...
(hives).
As of 2017, it is in
phase II clinical trial
Clinical trials are prospective biomedical or behavioral research studies on human participants designed to answer specific questions about biomedical or behavioral interventions, including new treatments (such as novel vaccines, drugs, diet ...
s for this indication.
The drug was also under investigation for the treatment of
allergic rhinitis
Allergic rhinitis, of which the seasonal type is called hay fever, is a type of inflammation in the nose that occurs when the immune system overreacts to allergens in the air. Signs and symptoms include a runny or stuffy nose, sneezing, red, i ...
(hay fever),
atopic dermatitis (atopic
eczema
Dermatitis is inflammation of the skin, typically characterized by itchiness, redness and a rash. In cases of short duration, there may be small blisters, while in long-term cases the skin may become thickened. The area of skin involved can ...
), and
contact dermatitis
Contact dermatitis is a type of acute or chronic inflammation of the skin caused by exposure to chemical or physical agents. Symptoms of contact dermatitis can include itchy or dry skin, a red rash, bumps, blisters, or swelling. These rashes are ...
, but development for these indications was discontinued.
See also
*
Esmirtazapine
*
Nordoxepin
Nordoxepin, also known as ''N''-desmethyldoxepin, is the major active metabolite of the tricyclic antidepressant (TCA) doxepin (Sinequan). It has been found to play a significant role in the antidepressant effects of doxepin.
Nordoxepin is a m ...
References
External links
Cidoxepin - AdisInsight
Dimethylamino compounds
Antihistamines
Dibenzoxepins
H1 receptor antagonists
Hypnotics
Muscarinic antagonists
Sedatives
Serotonin–norepinephrine reuptake inhibitors
Tricyclic antidepressants
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