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-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

| image = Azatadine.svg

| image_class = skin-invert-image

| tradename = Optimine

| Drugs.com = {{drugs.com|CONS|azatadine}}

| pregnancy_AU =

| pregnancy_US = B

| legal_AU =

| legal_UK =

| legal_US =

| 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

| 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.{{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 }}{{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 }}

It was patented in 1967.{{cite patent | title = Azatadine | inventor = Villani FJ, Caldwell W | country = US | number = 3326924 | gdate = 1967 }} It has been succeeded by both loratadine and desloratadine.{{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 }}{{rp|53}} and marketing approvals have been widely withdrawn.{{cite web | work = Drugs.com | url = https://www.drugs.com/mtm/azatadine.html | title = Azatadine }}{{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 }} {{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 }}{{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 }}{{rp|290}}{{cite web | work = FDA | url = https://www.fda.gov/Drugs/DevelopmentApprovalProcess/HowDrugsareDevelopedandApproved/ApprovalApplications/AbbreviatedNewDrugApplicationANDAGenerics/ucm283497.htm | title = OGD Suitability Tracking Report (Sorted by Drug Name) }}