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azatadine   Click here for help

GtoPdb Ligand ID: 7119

Synonyms: Optimine® | SCH-10649
Approved drug Immunopharmacology Ligand
azatadine is an approved drug (FDA (1977))
Compound class: Synthetic organic
Comment: Azatadine is a first-generation antihistamine and anticholinergic drug. Its marketing has been discontinued in many countries as its use has largely been repleaced by newer and more effective alternatives.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 0
Topological polar surface area 16.13
Molecular weight 290.18
XLogP 2.81
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CN1CCC(=C2c3ccccc3CCc3c2nccc3)CC1
Isomeric SMILES CN1CCC(=C2c3ccccc3CCc3c2nccc3)CC1
InChI InChI=1S/C20H22N2/c1-22-13-10-16(11-14-22)19-18-7-3-2-5-15(18)8-9-17-6-4-12-21-20(17)19/h2-7,12H,8-11,13-14H2,1H3
InChI Key SEBMTIQKRHYNIT-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US FDA (1977)
IUPAC Name Click here for help
11-(1-methylpiperidin-4-ylidene)-5,6-dihydrobenzo[1,2]cyclohepta[3,4-b]pyridine
International Nonproprietary Names Click here for help
INN number INN
2327 azatadine
Synonyms Click here for help
Optimine® | SCH-10649
Database Links Click here for help
CAS Registry No. 3964-81-6
ChEMBL Ligand CHEMBL946
DrugBank Ligand DB00719
DrugCentral Ligand 268
GtoPdb PubChem SID 178103696
PubChem CID 19861
Search Google for chemical match using the InChIKey SEBMTIQKRHYNIT-UHFFFAOYSA-N
Search Google for chemicals with the same backbone SEBMTIQKRHYNIT
Search PubMed clinical trials azatadine
Search PubMed titles azatadine
Search PubMed titles/abstracts azatadine
UniChem Compound Search for chemical match using the InChIKey SEBMTIQKRHYNIT-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey SEBMTIQKRHYNIT-UHFFFAOYSA-N
Wikipedia Azatadine