View source for Azatadine

{{short description|Chemical compound}}
{{cs1 config|name-list-style=vanc}}
{{distinguish|azetidine}}
{{Drugbox
| verifiedrevid = 477164914
| IUPAC_name = 11-(1-Methylpiperidin-4-ylidene)-6,11-dihydro-5''H''-benzo[5,6]cyclohepta[1,2-''b'']pyridine
| image = Azatadine.svg
| image_class = skin-invert-image
<!--Clinical data-->
| tradename = Optimine
| Drugs.com = {{drugs.com|CONS|azatadine}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = B
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
| legal_UK = <!-- GSL / P / POM / CD -->
| legal_US = 
<!--Identifiers-->
| IUPHAR_ligand = 7119
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 3964-81-6
| ATC_prefix = R06
| ATC_suffix = AX09
| PubChem = 19861
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00719
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 18709
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 94Z39NID6C
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07482
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 2946
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 946
<!--Chemical data-->
| C=20 | H=22 | N=2
| smiles = n4c3\C(=C1/CCN(C)CC1)c2ccccc2CCc3ccc4
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SEBMTIQKRHYNIT-UHFFFAOYSA-N
}}

'''Azatadine''' ('''Optimine''') is a [[first-generation antihistamine]] and [[anticholinergic]] drug that was synthesized in 1963 by [[Schering-Plough]], a former American pharmaceutical company.<ref>{{cite journal | vauthors = Katelaris C | title = Comparative effects of loratadine and azatadine in the treatment of seasonal allergic rhinitis | journal = Asian Pacific Journal of Allergy and Immunology | volume = 8 | issue = 2 | pages = 103–7 | date = December 1990 | pmid = 1982614 }}</ref><ref>{{cite journal | vauthors = Small P, Barrett D, Biskin N | title = Effects of azatadine, terfenadine, and astemizole on allergen-induced nasal provocation | journal = Annals of Allergy | volume = 64 | issue = 2 Pt 1 | pages = 129–31 | date = February 1990 | pmid = 1968324 }}</ref>

It was patented in 1967.<ref>{{cite patent | title = Azatadine | inventor = Villani FJ, Caldwell W | country = US | number = 3326924 | gdate = 1967 }}</ref>  It has been succeeded by both [[loratadine]] and [[desloratadine]].<ref>{{cite book | vauthors = Horak F | chapter = Antialergic and Vasoactive Drugs for Allergic Rhinitis. Chapter 4 | title = Allergy Frontiers:Therapy and Prevention. | volume = 5 | veditors = Pawankar R, Holgate ST, Rosenwasser LJ | publisher = Springer Science & Business Media | date = 2010 | isbn = 9784431993629 }}</ref>{{rp|53}} and marketing approvals have been widely withdrawn.<ref>{{cite web | work = Drugs.com | url = https://www.drugs.com/mtm/azatadine.html | title = Azatadine }}</ref><ref>{{cite web | work = Federal Register 70 FR 10651 | date = 2005 | url = https://www.federalregister.gov/articles/2005/03/04/05-4158/hospira-inc-et-al-withdrawal-of-approval-of-76-new-drug-applications-and-60-abbreviated-new-drug | author = Food and Drug Administration | title = Docket No.2005N-0058: Hospira, Inc. et al.; Withdrawal of Approval of 76 New Drug Applications and 60 Abbreviated New Drug Applications }} </ref><ref>{{cite web | work = Federal Register 72 FR 8184 | date = 2007 | url = http://www.gpo.gov/fdsys/pkg/FR-2007-02-23/html/E7-3043.htm | author = Food and Drug Administration | title = Docket No. 2004P-0262: Withdrawal of Approval of 128 Suitability Petitions }}</ref><ref>{{cite web | work = Department of Economic and Social Affairs of the United Nations Secretariat | url = https://www.un.org/esa/coordination/CL12.pdf | title = Consolidated List of Products Whose Consumption and/or Sale Have Been Banned, Withdrawn, Severely Restricted or not Approved by Governments Twelfth Issue: Pharmaceuticals | publisher = United Nations | location = New York | date = 2005 }}</ref>{{rp|290}}<ref>{{cite web | work = FDA | url = https://www.fda.gov/Drugs/DevelopmentApprovalProcess/HowDrugsareDevelopedandApproved/ApprovalApplications/AbbreviatedNewDrugApplicationANDAGenerics/ucm283497.htm | archive-url = https://web.archive.org/web/20111216053623/http://www.fda.gov/Drugs/DevelopmentApprovalProcess/HowDrugsareDevelopedandApproved/ApprovalApplications/AbbreviatedNewDrugApplicationANDAGenerics/ucm283497.htm | url-status = dead | archive-date = December 16, 2011 | title = OGD Suitability Tracking Report (Sorted by Drug Name) }}</ref>

== See also ==
* [[Azatadine/pseudoephedrine]]

== References ==
{{Reflist}}

{{Antihistamines}}
{{Cholinergics}}
{{Histaminergics}}
{{Tricyclics}}

[[Category:Piperidines]]
[[Category:Benzocycloheptapyridines]]
[[Category:H1 receptor antagonists]]
[[Category:Withdrawn drugs]]


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