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Identification
- Summary
Azatadine is an H1 receptor antagonist used to treat perennial and allergic rhinitis as well as eustachian tube congestion.
- Generic Name
- Azatadine
- DrugBank Accession Number
- DB00719
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Azatadine (DB00719)
- Weight
- Average: 290.4021
Monoisotopic: 290.178298714 - Chemical Formula
- C20H22N2
- Synonyms
- 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
- Azatadin
- Azatadina
- Azatadine
- Azatadinum
- External IDs
- Sch 10649
Pharmacology
- Indication
For the relief of the symptoms of upper respiratory mucosal congestion in perennial and allergic rhinitis, and for the relief of nasal congestion and eustachian t.b. congestion.
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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.
Target Actions Organism AHistamine H1 receptor antagonistHumans - Absorption
Well absorbed after oral administration.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hepatic.
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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The oral LD50 in mature rats and mice was greater than 1700 mg/kg and 600 mg/kg, respectively. Symptoms of overdose include clumsiness or unsteadiness, seizures, severe drowsiness, flushing or redness of face, hallucinations, muscle spasms (especially of neck and back), restlessness, shortness of breath, shuffling walk, tic-like (jerky) movements of head and face, trembling and shaking of hands, and insomnia.
- Pathways
Pathway Category Azatadine H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcetazolamide The therapeutic efficacy of Acetazolamide can be decreased when used in combination with Azatadine. Aclidinium The risk or severity of adverse effects can be increased when Azatadine is combined with Aclidinium. Acrivastine The risk or severity of QTc prolongation can be increased when Azatadine is combined with Acrivastine. Adenosine The risk or severity of QTc prolongation can be increased when Azatadine is combined with Adenosine. Ajmaline The risk or severity of QTc prolongation can be increased when Azatadine is combined with Ajmaline. - Food Interactions
- Avoid alcohol.
- Take with food. Food reduces irritation.
Products
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Ingredient UNII CAS InChI Key Azatadine maleate F3Q391WTX7 3978-86-7 SGHXFFAHXTZRQM-SPIKMXEPSA-N - International/Other Brands
- Idumed (NIHFI) / Optimine (Schering-Plough) / Zadine (Fulford)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Optimine Tab 1mg Tablet 1 mg Oral Schering Plough 1976-12-31 2009-08-04 Canada 
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Trinalin Repetabs Azatadine maleate (1 mg) + Pseudoephedrine sulfate (120 mg) Tablet, extended release Oral Schering Plough 1983-12-31 2007-08-03 Canada
Categories
- ATC Codes
- R06AX09 — Azatadine
- Drug Categories
- Agents that reduce seizure threshold
- Anticholinergic Agents
- Antihistamines for Systemic Use
- Benzocycloheptenes
- Cholinergic Agents
- Dibenzocycloheptenes
- Histamine Agents
- Histamine Antagonists
- Histamine H1 Antagonists
- Neurotransmitter Agents
- Piperidines
- Potential QTc-Prolonging Agents
- QTc Prolonging Agents
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzocycloheptapyridines. These are aromatic compounds containing a benzene ring and a pyridine ring fused to a seven membered carbocycle.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzocycloheptapyridines
- Sub Class
- Not Available
- Direct Parent
- Benzocycloheptapyridines
- Alternative Parents
- Pyridines and derivatives / Piperidines / Benzenoids / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Amine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzocycloheptapyridine / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- tertiary amine, benzocycloheptapyridine (CHEBI:2946)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 94Z39NID6C
- CAS number
- 3964-81-6
- InChI Key
- SEBMTIQKRHYNIT-UHFFFAOYSA-N
- 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
- IUPAC Name
- 2-(1-methylpiperidin-4-ylidene)-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3(8),4,6,11,13-hexaene
- SMILES
- CN1CCC(CC1)=C1C2=CC=CC=C2CCC2=C1N=CC=C2
References
- Synthesis Reference
Raymond E. Dagger, Linda A. Motyka, "Process for preparing intermediates for azatidine." U.S. Patent US4954632, issued September 04, 1990.
US4954632- General References
- Zhang D, Hansen EB Jr, Deck J, Heinze TM, Sutherland JB, Cerniglia CE: Fungal biotransformation of the antihistamine azatadine by Cunninghamella elegans. Appl Environ Microbiol. 1996 Sep;62(9):3477-9. [Article]
- Katelaris C: Comparative effects of loratadine and azatadine in the treatment of seasonal allergic rhinitis. Asian Pac J Allergy Immunol. 1990 Dec;8(2):103-7. [Article]
- Small P, Barrett D, Biskin N: Effects of azatadine, terfenadine, and astemizole on allergen-induced nasal provocation. Ann Allergy. 1990 Feb;64(2 Pt 1):129-31. [Article]
- External Links
- Human Metabolome Database
- HMDB0014857
- KEGG Compound
- C07774
- PubChem Compound
- 19861
- PubChem Substance
- 46507958
- ChemSpider
- 18709
- BindingDB
- 22868
- 18600
- ChEBI
- 2946
- ChEMBL
- CHEMBL946
- ZINC
- ZINC000000968337
- Therapeutic Targets Database
- DAP001079
- PharmGKB
- PA164747157
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Azatadine
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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Pharmacoeconomics
- Manufacturers
- Schering corp sub schering plough corp
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Syrup Oral 50.000 mg Tablet Oral 4.000 mg Tablet Oral 12.0000 mg Solution Oral Tablet Oral 500.000 mg Capsule Oral Tablet Oral 325.000 mg Tablet Oral 1 mg Tablet Oral Tablet, extended release Oral Capsule Oral 10.00 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 152-154 REM p. 1131 Villani, F.J.; U.S. Patents 3,326,924; January 20, 1967; 3,357,986; December 12, 1967; and 3,419,565; December 31,1968; all assigned to Schering Corp. water solubility Very soluble Not Available logP 3.59 BIOBYTE (1995) - Predicted Properties
Property Value Source Water Solubility 0.113 mg/mL ALOGPS logP 3.67 ALOGPS logP 3.75 Chemaxon logS -3.4 ALOGPS pKa (Strongest Basic) 7.91 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 16.13 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 101.53 m3·mol-1 Chemaxon Polarizability 34.02 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9973 Blood Brain Barrier + 0.9826 Caco-2 permeable + 0.7341 P-glycoprotein substrate Substrate 0.8357 P-glycoprotein inhibitor I Inhibitor 0.9232 P-glycoprotein inhibitor II Inhibitor 0.545 Renal organic cation transporter Inhibitor 0.8115 CYP450 2C9 substrate Non-substrate 0.8064 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.5716 CYP450 1A2 substrate Non-inhibitor 0.5801 CYP450 2C9 inhibitor Non-inhibitor 0.791 CYP450 2D6 inhibitor Inhibitor 0.6078 CYP450 2C19 inhibitor Non-inhibitor 0.8348 CYP450 3A4 inhibitor Non-inhibitor 0.835 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6425 Ames test Non AMES toxic 0.7616 Carcinogenicity Non-carcinogens 0.9692 Biodegradation Not ready biodegradable 0.9819 Rat acute toxicity 2.9760 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.804 hERG inhibition (predictor II) Inhibitor 0.6909
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-003r-1290000000-ca0638c59dea202e717c Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-a5a5284fa1153849759a Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0090000000-c454427b5f1538489516 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0090000000-917fa96d58887d29d09c Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0290000000-21196164ed237b90cc07 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-03kl-0490000000-21d14c3cc6908a608643 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0537-1690000000-11902c64f549c469b6dd Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 180.4477902 predictedDarkChem Lite v0.1.0 [M-H]- 180.6533902 predictedDarkChem Lite v0.1.0 [M-H]- 165.21999 predictedDeepCCS 1.0 (2019) [M+H]+ 181.5168902 predictedDarkChem Lite v0.1.0 [M+H]+ 181.7560902 predictedDarkChem Lite v0.1.0 [M+H]+ 167.57799 predictedDeepCCS 1.0 (2019) [M+Na]+ 181.0088902 predictedDarkChem Lite v0.1.0 [M+Na]+ 181.1577902 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.67114 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- G-protein-coupled receptor for histamine, a biogenic amine that functions as an immune modulator and a neurotransmitter (PubMed:33828102, PubMed:8280179). Through the H1 receptor, histamine mediates the contraction of smooth muscles and increases capillary permeability due to contraction of terminal venules. Also mediates neurotransmission in the central nervous system and thereby regulates circadian rhythms, emotional and locomotor activities as well as cognitive functions (By similarity)
- Specific Function
- G protein-coupled serotonin receptor activity
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Singh N, Puri SK: Causal prophylactic activity of antihistaminic agents against Plasmodium yoelii nigeriensis infection in Swiss mice. Acta Trop. 1998 Jun;69(3):255-60. [Article]
- Mann KV, Crowe JP, Tietze KJ: Nonsedating histamine H1-receptor antagonists. Clin Pharm. 1989 May;8(5):331-44. [Article]
- Clissold SP, Sorkin EM, Goa KL: Loratadine. A preliminary review of its pharmacodynamic properties and therapeutic efficacy. Drugs. 1989 Jan;37(1):42-57. [Article]
- Haria M, Fitton A, Peters DH: Loratadine. A reappraisal of its pharmacological properties and therapeutic use in allergic disorders. Drugs. 1994 Oct;48(4):617-37. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 30, 2024 23:02