Structure via PubChem · Public domain (PubChem)
azatadine
Sign in to saveAlso known as Optimine®, SCH-10649, 11-(1-Methyl-4-piperidinylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine, 6,11-Dihydro-11-(1-methyl-4-piperidylidene)-5H-benzo(5,6)cyclohepta(1,2-b)pyridine, Azatadina, Azatadinum, Azatadin
Azatadine (Optimine) is a first-generation antihistamine and anticholinergic drug that was synthesized in 1963 by Schering-Plough, a former American pharmaceutical company. It is a nitrogen analog of cyproheptadine.
Chemical data
- Formula
- C20H22N2
- Molecular weight
- 290.4 g/mol
- IUPAC name
- 2-(1-methylpiperidin-4-ylidene)-4-azatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaene
- SMILES
- CN1CCC(=C2C3=CC=CC=C3CCC4=C2N=CC=C4)CC1
- InChIKey
- SEBMTIQKRHYNIT-UHFFFAOYSA-N
- XLogP
- 3.6
- Polar surface area
- 16.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1977
- Admin. routes
- oral
- Indications
- allergic disease
via ChEMBL · EBI
Research
79 papers- Azatadine.2006
- Preclinical Screening Platform Identifies Azatadine-Dimaleate as a Potent Repurposed Therapeutic Against SARS-CoV-2 Infection.Journal of medical virology · 2025
- Azatadine maleate/pseudoephedrine sulfate repetabs versus placebo in the treatment of severe perennial allergic rhinitis.The Journal of international medical research · 1980
- Azatadine maleate in perennial allergic rhinitis: effects on clinical symptoms and choice reaction time.British journal of clinical pharmacology · 1980
- Azatadine (optimine)--a new antihistamine.The Medical letter on drugs and therapeutics · 1977
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 290.178299
- Has use
- medication
Show 7 more facts
- chemical formula
- C₂₀H₂₂N₂
- Commons category
- Azatadine
- medical condition treated
- urticaria
- canonical SMILES
- CN1CCC(=C2C3=CC=CC=C3CCC4=C2N=CC=C4)CC1
- World Health Organisation international non-proprietary name
- azatadine
- defined daily dose
- 2
- subject has role
- H1 antagonist
Sources (3)
via Wikidata · CC0
~2 min read
Encyclopedic overview
6 sectionsContents
- Pharmacology
- Field of application
- Mechanism of action
- Synthesis
- See also
- References
Azatadine (Optimine) is a first-generation antihistamine and anticholinergic drug that was synthesized in 1963 by Schering-Plough, a former American pharmaceutical company. It is a nitrogen analog of cyproheptadine.
It was patented in 1967. It has been succeeded by both loratadine and desloratadine. and marketing approvals have been widely withdrawn. == Pharmacology == Azatadine exhibits potent antihistamine, anticholinergic, antiserotonin, and antianaphylactic properties. Its anticholinergic potency is one-third that of atropine and equivalent to that of promethazine and cyproheptadine. Azatadine is among the more potent antianaphylactic agents.
Excerpted from Wikipedia’s “azatadine” article, available under the CC BY-SA 4.0 licence.