Azatadine

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Azatadine
Azatadine.svg
Clinical data
Trade names Optimine
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ATC code
Identifiers
  • 11-(1-Methylpiperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine
CAS Number
PubChem CID
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ChEBI
ChEMBL
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Chemical and physical data
Formula C20H22N2
Molar mass 290.410 g·mol−1
3D model (JSmol)
  • n4c3\C(=C1/CCN(C)CC1)c2ccccc2CCc3ccc4
  • 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 Yes check.svgY
  • Key:SEBMTIQKRHYNIT-UHFFFAOYSA-N Yes check.svgY
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Azatadine (Optimine) is a first-generation antihistamine and anticholinergic drug that was synthesized in 1963 by Schering-Plough, a former American pharmaceutical company. [1] [2] It is a nitrogen analog of cyproheptadine. [3]

Contents

It was patented in 1967. [4] It has been succeeded by both loratadine and desloratadine. [5] : 53  and marketing approvals have been widely withdrawn. [6] [7] [8] [9] : 290  [10]

Pharmacology

Azatadine exhibits potent antihistamine [11] , 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. [3]

Azatadine is a first-generation antihistamine. [12]

Field of application

The medicinal form of azatadine is the salt of maleic acid, azatadine maleate. It is described as an effective treatment for acute and chronic allergic rhinitis [11] , vasomotor rhinitis, urticaria, and certain forms of atopic and contact dermatitis. At the maximum recommended therapeutic dose of 4 mg per day, the drug markedly reduced the severity of perennial allergic rhinitis in most patients (80%) over a 7-day period and significantly decreased swelling in histamine provocation and allergen tests. It was generally well tolerated. Drowsiness was reported by 40% of patients. [13]

Mechanism of action

Antihistamines such as azatadine compete with histamine for the histamine H1 receptor on plasma cell. This antagonism counteracts the pharmacological effects of histamine mediated through H1 receptor activation, thereby reducing the intensity of allergic reactions and the tissue damage associated with histamine release. [14] In addition, azatadine has been shown to downregulate leukotrienes as part of the immediate allergic response. [12]

Synthesis

The multi-step synthesis has been described in the literature. [15]

See also

References

  1. ↑ Katelaris C (December 1990). "Comparative effects of loratadine and azatadine in the treatment of seasonal allergic rhinitis". Asian Pacific Journal of Allergy and Immunology. 8 (2): 103–7. PMID   1982614.
  2. ↑ Small P, Barrett D, Biskin N (February 1990). "Effects of azatadine, terfenadine, and astemizole on allergen-induced nasal provocation". Annals of Allergy. 64 (2 Pt 1): 129–31. PMID   1968324.
  3. 1 2 Salvatore Tozzi, Franklin E. Roth, Irving I. A. Tabachnick (1974-10-01), "The pharmacology of azatadine, a potential antiallergy drug", Agents and Actions, vol. 4, no. 4, pp. 264–270, doi:10.1007/BF01965229 {{citation}}: CS1 maint: multiple names: authors list (link)
  4. ↑ US 3326924,Villani FJ, Caldwell W,"Azatadine",issued 1967
  5. ↑ Horak F (2010). "Antialergic and Vasoactive Drugs for Allergic Rhinitis. Chapter 4". In Pawankar R, Holgate ST, Rosenwasser LJ (eds.). Allergy Frontiers:Therapy and Prevention. Vol. 5. Springer Science & Business Media. ISBN   9784431993629.
  6. ↑ "Azatadine". Drugs.com.
  7. ↑ Food and Drug Administration (2005). "Docket No.2005N-0058: Hospira, Inc. et al.; Withdrawal of Approval of 76 New Drug Applications and 60 Abbreviated New Drug Applications". Federal Register 70 FR 10651.
  8. ↑ Food and Drug Administration (2007). "Docket No. 2004P-0262: Withdrawal of Approval of 128 Suitability Petitions". Federal Register 72 FR 8184.
  9. ↑ "Consolidated List of Products Whose Consumption and/or Sale Have Been Banned, Withdrawn, Severely Restricted or not Approved by Governments Twelfth Issue: Pharmaceuticals" (PDF). Department of Economic and Social Affairs of the United Nations Secretariat. New York: United Nations. 2005.
  10. ↑ "OGD Suitability Tracking Report (Sorted by Drug Name)". FDA. Archived from the original on December 16, 2011.
  11. 1 2 George Milne (2018), Drugs: Synonyms and Properties, Routledge, p. 280, ISBN   978-1-351-78990-5
  12. 1 2 Lawrence M. Du Buske: Clinical comparison of histamine H1–receptor antagonist drugs. In: Journal of Allergy and Clinical Immunology, Bd. 98, Nr. 6, 1996, S. S307-S318, doi:10.1016/S0091-6749(96)80116-3
  13. ↑ Jl Hillas, Sd Somerfield, Jd Wilson, Mg Aman (December 1980), "Azatadine maleate in perennial allergic rhinitis: effects on clinical symptoms and choice reaction time", British Journal of Clinical Pharmacology , vol. 10, no. 6, pp. 573–577, doi:10.1111/j.1365-2125.1980.tb00513.x {{citation}}: CS1 maint: multiple names: authors list (link)
  14. ↑ "Azatadine". drugbank.com. go.drugbank.com. Retrieved 2025-11-17.
  15. ↑ A. Kleemann, J. Engel, B. Kutscher, D. Reichert (2014-05-14), Pharmaceutical Substances, 5th Edition, 2009: Syntheses, Patents and Applications of the most relevant APIs, Georg Thieme Verlag, ISBN   978-3-13-179525-0 {{citation}}: CS1 maint: multiple names: authors list (link)


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