Basic information
- CAS
3964-81-6- Standard SMILES
CN1CCC(=C2c3ccccc3CCc3cccnc32)CC1- InChIKey
SEBMTIQKRHYNIT-UHFFFAOYSA-N- Molecular formula
- C20H22N2
- Average molar mass
- 290.4 g/mol
- Monoisotopic mass
- 290.1782987
Overview
Azatadine is a benzo[5,6]cyclohepta[1,2-b]pyridine having a 1-methylpiperidin-4-ylidene group at the 11-position. It has a role as a H1-receptor antagonist and an anti-allergic agent. It is a tertiary amine and a benzocycloheptapyridine.
Names & identifiers
- Preferred name
- Azatadine
- IUPAC
- 2-(1-methylpiperidin-4-ylidene)-4-azatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaene
- English name
- Azatadine
- Molecular formula
- C20H22N2
- Molecular weight
- 290.4
Names & synonyms
AZATADINE3964-81-6AzatadinaAzatadinumDTXSID602263694Z39NID6C6,11-Dihydro-11-(1-methyl-4-piperidylidene)-5H-benzo(5,6)cyclohepta(1,2-b)pyridineCHEBI:2946DTXCID70263611-(1-Methyl-4-piperidinylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine2-(1-methylpiperidin-4-ylidene)-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaeneIdulamine
Show more names
Azatadine USP/EP/BPDesloratadine Impurity 256,11-Dihydro-11-(1-methyl-4-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine11-(1-methylpiperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine6,11-Dihydro-11-(1-Methyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine6,11-Dihydro-11-(1-methylpiperidin-4-ylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine5H-Benzo[5,6]cyclohepta[1,2-b]pyridine, 6,11-dihydro-11-(1-Methyl-4-piperidinylidene)-
11-(1-Methyl-4-piperidinylidene)-6,11-dihydro-5H-benzo(5,6)cyclohepta(1,2-b)pyridine11-(1-methylpiperidin-4-ylidene)-5,6-dihydrobenzo(1,2)cyclohepta(3,4-b)pyridine11-(1-methylpiperidin-4-ylidene)-5,6-dihydrobenzo[1,2]cyclohepta[3,4-b]pyridine2-(1-methylpiperidin-4-ylidene)-4-azatricyclo(9.4.0.0^(3,8))pentadeca-1(11),3,5,7,12,14-hexaeneRefChem:560457R06AX09AzatadineMaleateAzatadinum [INN-Latin]
Properties
Computed structural properties
- XLogP
- 3.6
- Topological polar surface area
- 16.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 417
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP
2.8
3.59
Solubility
Very soluble
1.13e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihistamines
Pharmaceuticals
Melting Point152-154
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 124 · 124-126°
- Boiling point
- 450.1 · 450.1±45.0 °C(Predicted)
- Density
- 1.127 · 1.127
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Soluble in DMSO
- form
- Powder
Safety & regulation
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
azatadine
DILI Positive
Oral
DOI:10.1016/j.drudis.2019.09.022
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P264-P280-P302+P352-P321-P332+P313-P362-P305+P351+P338-P337+P313-P261-P271-P304+P340-P312-P403+P233-P405-P501
Chemistry & industry
Pharmacology
ATC Code
R - Respiratory system
QR - Respiratory system
Pharmacodynamics
Azatadine is an antihistamine, related to cyproheptadine, with anti-serotonin, anticholinergic (drying), and sedative effects. Azatadine is in the same class of drugs as chlorpromazine (Thorazine) and trifluoperazine (Stelazine); however, unlike the other drugs in this class, azatadine is not used clinically as an anti-psychotic. Antihistamines antagonize the vasodilator effect of endogenously released histamine, especially in small vessels, and mitigate the effect of histamine which results in increased capillary permeability and edema formation. As consequences of these actions, antihistamines antagonize the physiological manifestations of histamine release in the nose following antigen-antibody interaction, such as congestion related to vascular engorgement, mucosal edema, and profuse, watery secretion, and irritation and sneezing resulting from histamine action on afferent nerve terminals.
Mechanism of Action
Antihistamines such as azatadine appear to compete with histamine for histamine H1- receptor sites on effector cells. The antihistamines antagonize those pharmacological effects of histamine which are mediated through activation of H1- receptor sites and thereby reduce the intensity of allergic reactions and tissue injury response involving histamine release.
Metabolism/MetabolitesHepatic.
MeSH Pharmacological Classification
Drugs that selectively bind to but do not activate histamine H1 receptors, thereby blocking the actions of endogenous histamine. Included here are the classical antihistaminics that antagonize or prevent the action of histamine mainly in immediate hypersensitivity. They act in the bronchi, capillaries, and some other smooth muscles, and are used to prevent or allay motion sickness, seasonal rhinitis, and allergic dermatitis and to induce somnolence. The effects of blocking central nervous system H1 receptors are not as well understood.
Drugs that bind to but do not activate CHOLINERGIC RECEPTORS, thereby blocking the actions of ACETYLCHOLINE or cholinergic agonists.
Related reactions
16 records
Compound notes
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