General Information of Drug (ID: DMZ80SB)

Drug Name
Azatadine
Synonyms
Azatadina; Azatadinum; Azatidine; Azatadine maleate; Azatadina [INN-Spanish]; Azatadine (INN); Azatadine [INN:BAN]; Azatadinum [INN-Latin]; 11-(1-Methyl-4-piperidinylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine; 11-(1-methylpiperidin-4-ylidene)-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
Indication
Disease Entry ICD 11 Status REF
Allergic rhinitis CA08.0 Approved [1]
Common cold CA00 Approved [2]
Seasonal allergic rhinitis CA08.01 Approved [2]
Urticaria EB00-EB05 Approved [2]
Vasomotor/allergic rhinitis CA08 Approved [2]
Pruritus EC90 Investigative [2]
⏷ Show the Full List of Indication(s)
Therapeutic Class
Antihistamines
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 290.4
Logarithm of the Partition Coefficient (xlogp) 3.6
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Absorption
The drug is well absorbed after oral administration []
Metabolism
The drug is metabolized via the hepatic []
Chemical Identifiers
Formula
C20H22N2
IUPAC Name
2-(1-methylpiperidin-4-ylidene)-4-azatricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaene
Canonical SMILES
CN1CCC(=C2C3=CC=CC=C3CCC4=C2N=CC=C4)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
InChIKey
SEBMTIQKRHYNIT-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
19861
ChEBI ID
CHEBI:2946
CAS Number
3964-81-6
DrugBank ID
DB00719
TTD ID
D0N7AD
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Histamine H1 receptor (H1R) TTTIBOJ HRH1_HUMAN Antagonist [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Allergic rhinitis
ICD Disease Classification CA08.0
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Histamine H1 receptor (H1R) DTT HRH1 6.74E-01 0.13 0.43
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Azatadine
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Chlorpheniramine DM5URA2 Moderate Additive anticholinergic effects by the combination of Azatadine and Chlorpheniramine. Vasomotor/allergic rhinitis [CA08] [4]
Carbinoxamine DMCT31R Moderate Additive anticholinergic effects by the combination of Azatadine and Carbinoxamine. Vasomotor/allergic rhinitis [CA08] [4]
Brompheniramine DMFOVSD Moderate Additive anticholinergic effects by the combination of Azatadine and Brompheniramine. Vasomotor/allergic rhinitis [CA08] [4]
Acrivastine DMTIGA0 Moderate Additive anticholinergic effects by the combination of Azatadine and Acrivastine. Vasomotor/allergic rhinitis [CA08] [5]
Coadministration of a Drug Treating the Disease Different from Azatadine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Scopolamine DMOM8AL Moderate Additive anticholinergic effects by the combination of Azatadine and Scopolamine. Addictive disorder [6C50-6C5Z] [4]
Mepyramine DMB4SFH Moderate Additive anticholinergic effects by the combination of Azatadine and Mepyramine. Allergic/hypersensitivity disorder [4A80-4A8Z] [5]
Phenyltoloxamine DMKAEQW Moderate Additive anticholinergic effects by the combination of Azatadine and Phenyltoloxamine. Allergic/hypersensitivity disorder [4A80-4A8Z] [5]
Memantine DMD9WSC Moderate Additive anticholinergic effects by the combination of Azatadine and Memantine. Alzheimer disease [8A20] [4]
Rivastigmine DMG629M Moderate Antagonize the effect of Azatadine when combined with Rivastigmine. Alzheimer disease [8A20] [6]
Donepezil DMIYG7Z Moderate Antagonize the effect of Azatadine when combined with Donepezil. Alzheimer disease [8A20] [6]
Desipramine DMT2FDC Moderate Additive anticholinergic effects by the combination of Azatadine and Desipramine. Attention deficit hyperactivity disorder [6A05] [4]
Cariprazine DMJYDVK Moderate Additive anticholinergic effects by the combination of Azatadine and Cariprazine. Bipolar disorder [6A60] [4]
Loperamide DMOJZQ9 Moderate Additive antimotility effects by the combination of Azatadine and Loperamide. Bowel habit change [ME05] [7]
Acetylcholine DMDF79Z Moderate Antagonize the effect of Azatadine when combined with Acetylcholine. Cataract [9B10] [8]
Umeclidinium DM4E8O9 Moderate Additive anticholinergic effects by the combination of Azatadine and Umeclidinium. Chronic obstructive pulmonary disease [CA22] [9]
Tiotropium DMFDC0Q Moderate Additive anticholinergic effects by the combination of Azatadine and Tiotropium. Chronic obstructive pulmonary disease [CA22] [9]
Revefenacin DMMP5SI Moderate Additive anticholinergic effects by the combination of Azatadine and Revefenacin. Chronic obstructive pulmonary disease [CA22] [9]
Ethanol DMDRQZU Moderate Additive CNS depression effects by the combination of Azatadine and Ethanol. Cystitis [GC00] [10]
Trimipramine DM1SC8M Moderate Additive anticholinergic effects by the combination of Azatadine and Trimipramine. Depression [6A70-6A7Z] [4]
Cyclobenzaprine DM1YBRM Moderate Additive anticholinergic effects by the combination of Azatadine and Cyclobenzaprine. Depression [6A70-6A7Z] [4]
Isocarboxazid DMAF1NB Moderate Additive CNS depression effects by the combination of Azatadine and Isocarboxazid. Depression [6A70-6A7Z] [11]
Tranylcypromine DMGB5RE Moderate Additive CNS depression effects by the combination of Azatadine and Tranylcypromine. Depression [6A70-6A7Z] [11]
OPC-34712 DMHG57U Moderate Additive anticholinergic effects by the combination of Azatadine and OPC-34712. Depression [6A70-6A7Z] [4]
Phenelzine DMHIDUE Moderate Additive CNS depression effects by the combination of Azatadine and Phenelzine. Depression [6A70-6A7Z] [11]
Clomipramine DMINRKW Moderate Additive anticholinergic effects by the combination of Azatadine and Clomipramine. Depression [6A70-6A7Z] [4]
Doxepin DMPI98T Moderate Additive anticholinergic effects by the combination of Azatadine and Doxepin. Depression [6A70-6A7Z] [4]
Maprotiline DMPWB7T Moderate Additive anticholinergic effects by the combination of Azatadine and Maprotiline. Depression [6A70-6A7Z] [4]
Esketamine DMVU687 Moderate Additive CNS depression effects by the combination of Azatadine and Esketamine. Depression [6A70-6A7Z] [12]
Mepenzolate DM8YU2F Moderate Additive anticholinergic effects by the combination of Azatadine and Mepenzolate. Digestive system disease [DE2Z] [5]
Oxybutynine DMJPBAX Moderate Additive anticholinergic effects by the combination of Azatadine and Oxybutynine. Discovery agent [N.A.] [4]
Meclizine DMS7T13 Moderate Additive anticholinergic effects by the combination of Azatadine and Meclizine. Dizziness and giddiness [MB48] [4]
Zonisamide DM0DTF7 Major Additive CNS depression effects by the combination of Azatadine and Zonisamide. Epilepsy/seizure [8A61-8A6Z] [13]
Diphenhydramine DMKQTBA Moderate Additive anticholinergic effects by the combination of Azatadine and Diphenhydramine. Episodic vestibular syndrome [AB31] [4]
Solifenacin DMG592Q Moderate Additive anticholinergic effects by the combination of Azatadine and Solifenacin. Functional bladder disorder [GC50] [4]
Tolterodine DMSHPW8 Moderate Additive anticholinergic effects by the combination of Azatadine and Tolterodine. Functional bladder disorder [GC50] [4]
Propantheline DM2EN6G Moderate Additive anticholinergic effects by the combination of Azatadine and Propantheline. Gastric ulcer [DA60] [4]
Pilocarpine DMV9ADG Moderate Antagonize the effect of Azatadine when combined with Pilocarpine. Glaucoma [9C61] [8]
Procarbazine DMIK367 Moderate Additive CNS depression effects by the combination of Azatadine and Procarbazine. Hodgkin lymphoma [2B30] [11]
Belladonna DM2RBWK Moderate Additive anticholinergic effects by the combination of Azatadine and Belladonna. Infectious gastroenteritis/colitis [1A40] [4]
Amantadine DMS3YE9 Moderate Additive anticholinergic effects by the combination of Azatadine and Amantadine. Influenza [1E30-1E32] [14]
ITI-007 DMUQ1DO Moderate Additive anticholinergic effects by the combination of Azatadine and ITI-007. Insomnia [7A00-7A0Z] [4]
Clidinium DMUMQZ0 Moderate Additive anticholinergic effects by the combination of Azatadine and Clidinium. Irritable bowel syndrome [DD91] [4]
Dicyclomine DMZSDGX Moderate Additive anticholinergic effects by the combination of Azatadine and Dicyclomine. Irritable bowel syndrome [DD91] [4]
Physostigmine DM2N0TO Moderate Antagonize the effect of Azatadine when combined with Physostigmine. Lips/oral mucosa miscellaneous disorder [DA02] [6]
Allopregnanolone DMNLHAC Moderate Additive CNS depression effects by the combination of Azatadine and Allopregnanolone. Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z] [15]
Lasmiditan DMXLVDT Moderate Additive CNS depression effects by the combination of Azatadine and Lasmiditan. Migraine [8A80] [16]
Flibanserin DM70DTN Moderate Additive CNS depression effects by the combination of Azatadine and Flibanserin. Mood disorder [6A60-6E23] [17]
Thalidomide DM70BU5 Moderate Additive CNS depression effects by the combination of Azatadine and Thalidomide. Multiple myeloma [2A83] [10]
Dimenhydrinate DM264B3 Moderate Additive anticholinergic effects by the combination of Azatadine and Dimenhydrinate. Nausea/vomiting [MD90] [4]
Promethazine DM6I5GR Moderate Additive anticholinergic effects by the combination of Azatadine and Promethazine. Nausea/vomiting [MD90] [4]
Apraclonidine DMO4PVE Moderate Additive CNS depression effects by the combination of Azatadine and Apraclonidine. Optic nerve disorder [9C40] [18]
Flavoxate DMKV4NL Moderate Additive anticholinergic effects by the combination of Azatadine and Flavoxate. Pain [MG30-MG3Z] [4]
Biperiden DME78OA Moderate Additive anticholinergic effects by the combination of Azatadine and Biperiden. Parkinsonism [8A00] [5]
Orphenadrine DMW542E Moderate Additive anticholinergic effects by the combination of Azatadine and Orphenadrine. Parkinsonism [8A00] [4]
Methylscopolamine DM5VWOB Moderate Additive anticholinergic effects by the combination of Azatadine and Methylscopolamine. Peptic ulcer [DA61] [4]
Quetiapine DM1N62C Moderate Additive anticholinergic effects by the combination of Azatadine and Quetiapine. Schizophrenia [6A20] [4]
Mesoridazine DM2ZGAN Moderate Additive anticholinergic effects by the combination of Azatadine and Mesoridazine. Schizophrenia [6A20] [5]
Aripiprazole DM3NUMH Moderate Additive anticholinergic effects by the combination of Azatadine and Aripiprazole. Schizophrenia [6A20] [4]
Iloperidone DM6AUFY Moderate Additive anticholinergic effects by the combination of Azatadine and Iloperidone. Schizophrenia [6A20] [4]
Paliperidone DM7NPJS Moderate Additive anticholinergic effects by the combination of Azatadine and Paliperidone. Schizophrenia [6A20] [4]
Perphenazine DMA4MRX Moderate Additive anticholinergic effects by the combination of Azatadine and Perphenazine. Schizophrenia [6A20] [4]
Molindone DMAH70G Moderate Additive anticholinergic effects by the combination of Azatadine and Molindone. Schizophrenia [6A20] [4]
Thiothixene DMDINC4 Moderate Additive anticholinergic effects by the combination of Azatadine and Thiothixene. Schizophrenia [6A20] [4]
Trifluoperazine DMKBYWI Moderate Additive anticholinergic effects by the combination of Azatadine and Trifluoperazine. Schizophrenia [6A20] [4]
Risperidone DMN6DXL Moderate Additive anticholinergic effects by the combination of Azatadine and Risperidone. Schizophrenia [6A20] [4]
Asenapine DMSQZE2 Moderate Additive anticholinergic effects by the combination of Azatadine and Asenapine. Schizophrenia [6A20] [4]
Pimozide DMW83TP Moderate Additive anticholinergic effects by the combination of Azatadine and Pimozide. Schizophrenia [6A20] [4]
⏷ Show the Full List of 63 DDI Information of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7119).
2 Azatadine FDA Label
3 Comparative effects of loratadine and azatadine in the treatment of seasonal allergic rhinitis. Asian Pac J Allergy Immunol. 1990 Dec;8(2):103-7.
4 Cohen MA, Alfonso CA, Mosquera M. Development of urinary retention during treatment with clozapine and meclizine [published correction appears in Am J Psychiatry 1994 Jun;151(6):952]. Am J Psychiatry. 1994;151(4):619-620. [PMID: 8147469]
5 Kulik AV, Wilbur R "Delirium and stereotypy from anticholinergic antiparkinson drugs." Prog Neuropsychopharmacol Biol Psychiatry 6 (1982): 75-82. [PMID: 7202232]
6 Beers MH, Ouslander JG, Rollingher I, Reuben DB, Brooks J, Beck JC "Explicit criteria for determining inappropriate medication use in nursing home residents." Arch Intern Med 151 (1991): 1825-32. [PMID: 1888249]
7 Eronen M, Putkonen H, Hallikainen T, Vartiainen H "Lethal gastroenteritis associated with clozapine and loperamide." Am J Psychiatry 160 (2003): 2242-2243. [PMID: 14638602]
8 Multum Information Services, Inc. Expert Review Panel.
9 Cole JM, Sheehan AH, Jordan JK "Concomitant use of ipratropium and tiotropium in chronic obstructive plmonary disease." Ann Pharmacother 46 (2012): 1717-21. [PMID: 23170031]
10 Warrington SJ, Ankier SI, Turner P "Evaluation of possible interactions between ethanol and trazodone or amitriptyline." Neuropsychobiology 15 (1986): 31-7. [PMID: 3725002]
11 Canadian Pharmacists Association.
12 Cerner Multum, Inc. "Australian Product Information.".
13 Product Information. Zonegran (zonisamide) Elan Pharmaceuticals, S. San Francisco, CA.
14 Postma JU, van Tilburg W "Visual hallucinations and delirium during treatment with amantadine (Symmetrel)." J Am Geriatr Soc 23 (1975): 212-5. [PMID: 123540]
15 Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
16 Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
17 Product Information. Addyi (flibanserin). Sprout Pharmaceuticals, Raleigh, NC.
18 Product Information. Alphagan (brimonidine ophthalmic). Allergan Inc, Irvine, CA.