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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
Structure of CIDOXEPIN

SMILES

CN(C)CC\C=C1\C2=C(COC3=C1C=CC=C3)C=CC=C2

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-

HIDE SMILES / InChI

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Single dose pharmacokinetics of doxepin in healthy volunteers.
1980 Nov
Protein binding of doxepin and desmethyldoxepin.
1982 Aug
Pharmacologic therapy for urticaria.
1997 Jan-Feb
Contributions of CYP2D6, CYP2C9 and CYP2C19 to the biotransformation of E- and Z-doxepin in healthy volunteers.
2002 Oct
Pain, pain, go away: antidepressants and pain management.
2008 Dec
Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:35:31 UTC 2023
Edited
by admin
on Sat Dec 16 17:35:31 UTC 2023
Record UNII
F96TTB8728
Record Status Validated (UNII)
Record Version
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Name Type Language
CIDOXEPIN
INN  
INN  
Official Name English
DOXEPIN IMPURITY D
Common Name English
DOXEPIN TRANS-FORM HYDROCHLORIDE [MI]
Common Name English
(Z)-3-(DIBENZO(B,E)OXEPIN-11(6H)-YLIDENE)-N,N-DIMETHYLPROPAN-1-AMINE
Systematic Name English
cidoxepin [INN]
Common Name English
DOXEPIN HYDROCHLORIDE IMPURITY D [EP IMPURITY]
Common Name English
DOXEPIN TRANS-FORM HYDROCHLORIDE
MI  
Common Name English
DOXEPIN, (Z)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C94727
Created by admin on Sat Dec 16 17:35:31 UTC 2023 , Edited by admin on Sat Dec 16 17:35:31 UTC 2023
Code System Code Type Description
INN
2316
Created by admin on Sat Dec 16 17:35:31 UTC 2023 , Edited by admin on Sat Dec 16 17:35:31 UTC 2023
PRIMARY
FDA UNII
F96TTB8728
Created by admin on Sat Dec 16 17:35:31 UTC 2023 , Edited by admin on Sat Dec 16 17:35:31 UTC 2023
PRIMARY
ChEMBL
CHEMBL101740
Created by admin on Sat Dec 16 17:35:31 UTC 2023 , Edited by admin on Sat Dec 16 17:35:31 UTC 2023
PRIMARY
EVMPD
SUB06258MIG
Created by admin on Sat Dec 16 17:35:31 UTC 2023 , Edited by admin on Sat Dec 16 17:35:31 UTC 2023
PRIMARY
MERCK INDEX
m4753
Created by admin on Sat Dec 16 17:35:31 UTC 2023 , Edited by admin on Sat Dec 16 17:35:31 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB14750
Created by admin on Sat Dec 16 17:35:31 UTC 2023 , Edited by admin on Sat Dec 16 17:35:31 UTC 2023
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WIKIPEDIA
Cidoxepin
Created by admin on Sat Dec 16 17:35:31 UTC 2023 , Edited by admin on Sat Dec 16 17:35:31 UTC 2023
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NCI_THESAURUS
C65328
Created by admin on Sat Dec 16 17:35:31 UTC 2023 , Edited by admin on Sat Dec 16 17:35:31 UTC 2023
PRIMARY
CAS
3607-18-9
Created by admin on Sat Dec 16 17:35:31 UTC 2023 , Edited by admin on Sat Dec 16 17:35:31 UTC 2023
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PUBCHEM
667468
Created by admin on Sat Dec 16 17:35:31 UTC 2023 , Edited by admin on Sat Dec 16 17:35:31 UTC 2023
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SMS_ID
100000081289
Created by admin on Sat Dec 16 17:35:31 UTC 2023 , Edited by admin on Sat Dec 16 17:35:31 UTC 2023
PRIMARY
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SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY