Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C19H21NO |
| Molecular Weight | 279.3761 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CC\C=C1\C2=CC=CC=C2COC3=CC=CC=C13
InChI
InChIKey=ODQWQRRAPPTVAG-BOPFTXTBSA-N
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-
| Molecular Formula | C19H21NO |
| Molecular Weight | 279.3761 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
Cidoxepin is the cis-isomer of the widely prescribed tricyclic compound doxepin. Commercial preparations of the tricyclic anti-depressant doxepin contain 15% of the more active cis-doxepin and 85% of the trans-isomer. Elorac, Inc., a rapidly growing specialty pharmaceutical company focused on the treatment of dermatological disorders, is pleased to announce that it has acquired worldwide rights to the active agent Cidoxepin from Gideon Pharmaceuticals. Cidoxepin appears to be much more potent than doxepin while having less sedative and cholinergic side effects. Elorac plans to develop oral formulations of the drug to treat urticaria and topical formulations for treatment of atopic and contact dermatitis.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL289 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11037801 |
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Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12180536 |
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Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12180536 |
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Target ID: CHEMBL3397 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12180536 |
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Target ID: CHEMBL231 |
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Target ID: GO:0051610 |
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Target ID: GO:0051620 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pain, pain, go away: antidepressants and pain management. | 2008-12 |
|
| Contributions of CYP2D6, CYP2C9 and CYP2C19 to the biotransformation of E- and Z-doxepin in healthy volunteers. | 2002-10 |
|
| Pharmacologic therapy for urticaria. | 1997-01-01 |
|
| Protein binding of doxepin and desmethyldoxepin. | 1982-08 |
|
| Single dose pharmacokinetics of doxepin in healthy volunteers. | 1980-11 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.google.com/patents/US7629378
Curator's Comment: Oral cidoxepin is in phase 2 trial for the treatment of urticaria. Dosage is unknown.
http://eloracpharma.com/pipeline/
The formulations used in the following examples were made using a cis doxepin composition prepared by Sigma Aldrich, Inc. of Sheboygan, Wis., the composition comprising not less than about 85% of the cis-isomer, with the balance of the composition being the trans-isomer. Amounts of cis doxepin as stated in the examples are the actual amounts of the cis doxepin isomer in each formulation.Example 1Cis doxepin isomer is incorporated into hard gelatin capsules in a dosage of 10 mg/capsule, and is administered once or twice daily to patients with acute or chronic urticaria in order to prevent new urticarial lesions.Example 2A cream containing cis doxepin isomer 1.0% by weight is applied two to four times daily to pruritic skin lesions by patients with atopic dermatitis. Application of this cream provides for relief of itching as well as more prompt resolution of the skin lesions without producing the incidence or severity of sedation observed with application of prior art doxepin containing creams in which the trans isomer is predominant.Example 3An aqueous solution of 0.2% by weight of the cis doxepin isomer is administered by nasal spray to the noses of patients with allergic rhinitis to treat and prevent nasal stuffiness.Example 4An aqueous solution of 0.1% by weight of the cis doxepin isomer is applied to the eyes of patients with allergic conjunctivitis to relieve symptoms of eye irritation.Example 5Suppositories containing 20 mg by weight of the cis doxepin isomer in a hydrogenated coglyceride base are inserted rectally twice to three times daily for relief of pain and/or itching in patients with proctitis or pruritis ani.Example 6Cis doxepin is incorporated into tablets containing 50 mg by weight of the cis doxepin isomer and such tablets are administered orally once to four times daily to patients with affective disorders so as to relieve feelings of depression or anxiety without producing substantial sedation in such patients.
Route of Administration:
Other
| Substance Class |
Chemical
Created
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admin
on
Edited
Wed Apr 02 09:19:41 GMT 2025
by
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Wed Apr 02 09:19:41 GMT 2025
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F96TTB8728
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Validated (UNII)
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NCI_THESAURUS |
C94727
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CHEMBL101740
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DB14750
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Cidoxepin
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C65328
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100000081289
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |