Azatadine

Azatadine
Clinical data

Trade names	Optimine
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Pregnancy category	US: B (No risk in non-human studies)
ATC code	R06AX09 (WHO)
Legal status
Legal status	US: Withdrawn
Identifiers
IUPAC name 11-(1-methylpiperidin-4-ylidene)-6,11-dihydro- 5H-benzo[5,6]cyclohepta[1,2-b]pyridine
CAS Number	3964-81-6^Y
PubChem (CID)	19861
IUPHAR/BPS	7119
DrugBank	DB00719^Y
ChemSpider	18709^Y
UNII	94Z39NID6C^Y
KEGG	D07482^Y
ChEBI	CHEBI:2946^Y
ChEMBL	CHEMBL946^Y
Chemical and physical data
Formula	C₂₀H₂₂N₂
Molar mass	290.402 g/mol
3D model (Jmol)	Interactive image
SMILES n4c3\C(=C1/CCN(C)CC1)c2ccccc2CCc3ccc4
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^Y Key:SEBMTIQKRHYNIT-UHFFFAOYSA-N^Y
(verify)

Azatadine (Optimine) is a first-generation antihistamine and anticholinergic that was launched Schering-Plough in 1973.^[1]^[2]

It was patented in 1967.^[3] It has been succeeded by other antihistamines^[4]^:53 and marketing approvals have been widely withdrawn.^[5]^[6]^[7]^[8]^:290^[9]

References

↑ Katelaris, C. (1990). "Comparative effects of loratadine and azatadine in the treatment of seasonal allergic rhinitis". Asian Pacific Journal of Allergy and Immunology. 8 (2): 103–107. PMID 1982614.
↑ Small, P.; Barrett, D.; Biskin, N. (1990). "Effects of azatadine, terfenadine, and astemizole on allergen-induced nasal provocation". Annals of allergy. 64 (2 Pt 1): 129–131. PMID 1968324.
↑ Azatadine, Villani, F. J.; Caldwell, W. U.S. Patent 3,326,924 (1967).
↑ Horak F. Antialergic and Vasoactive Drugs for Allergic Rhinitis. Chapter 4 in Allergy Frontiers:Therapy and Prevention. Volume 5 of Allergy Frontiers. Eds Pawankar R et al Springer Science & Business Media, 2010 ISBN 9784431993629
↑ Drugs.com Drugs.com listing for Azatadine Page accessed July 3, 2015
↑ Federal Register 2005 Food and Drug Administration Docket No.2005N-0058: Hospira, Inc. et al.; Withdrawal of Approval of 76 New Drug Applications and 60 Abbreviated New Drug Applications 70 FR 10651
↑ Federal Register 2007 Food and Drug Administration Docket No. 2004P-0262: Withdrawal of Approval of 128 Suitability Petitions 72 FR 8184
↑ Department of Economic and Social Affairs of the United Nations Secretariat Consolidated List of Products Whose Consumption and/or Sale Have Been Banned, Withdrawn, Severely Restricted or not Approved by Governments Twelfth Issue: Pharmaceuticals United Nations – New York, 2005
↑ FDA OGD Suitability Tracking Report (Sorted by Drug Name) Page accessed July 3, 2015

Antihistamines (R06)

Aminoalkyl ethers	Bromazine (bromodiphenhydramine) Carbinoxamine Clemastine Chlorphenoxamine Diphenylpyraline Diphenhydramine Doxylamine Orphenadrine Phenyltoloxamine

Substituted alkylamines	Brompheniramine Chlorphenamine Dexbrompheniramine (+pseudoephedrine) Dexchlorpheniramine (+betamethasone) Dimetindene Pheniramine Talastine

Substituted ethylenediamines	Chloropyramine Histapyrrodine Mepyramine Methapyrilene Tripelennamine (pyribenzamine)

Phenothiazine derivatives	Alimemazine Fenethazine Hydroxyethylpromethazine Isothipendyl Mequitazine Methdilazine Oxomemazine Promethazine

Piperazine derivatives	Buclizine Cetirizine Levocetirizine Chlorcyclizine Cinnarizine Cyclizine Hydroxyzine Meclizine Oxatomide

Others for systemic use	Antazoline Azanator Azatadine Bamipine Cyproheptadine Deptropine Ebastine Emedastine Epinastine Ketotifen Latrepirdine Mebhydrolin Mizolastine Olopatadine Phenindamine Pimethixene Pyrrobutamine Quifenadine Rupatadine Triprolidine selective (Acrivastine Astemizole Azelastine Bilastine Desloratadine Fexofenadine Loratadine Terfenadine)

For topical use	Bamipine Chloropyramine Chlorphenoxamine Clemastine Dimetindene Diphenhydramine Isothipendyl Mepyramine Promethazine Thenalidine

Cholinergics

Receptor ligands

mACh	Muscarinic agonists: 77-LH-28-1 AC-42 AC-260,584 Aceclidine Acetylcholine AF30 AF150(S) AF267B AFDX-384 Alvameline AQRA-741 Arecoline Bethanechol Butyrylcholine Carbachol CDD-0034 CDD-0078 CDD-0097 CDD-0098 CDD-0102 Cevimeline Choline cis-Dioxolane Ethoxysebacylcholine Itameline LY-593,039 L-689,660 LY-2,033,298 McNA343 Methacholine Milameline Muscarine NGX-267 Ocvimeline Oxotremorine PD-151,832 Pilocarpine RS86 Sabcomeline SDZ 210-086 Sebacylcholine Suberyldicholine Talsaclidine Tazomeline Thiopilocarpine Vedaclidine VU-0029767 VU-0090157 VU-0152099 VU-0152100 VU-0238429 WAY-132,983 Xanomeline YM-796 Muscarinic antagonists: 3-Quinuclidinyl benzilate 4-DAMP Aclidinium bromide Anisodamine Anisodine Antihistamines (first-generation) (e.g., brompheniramine, chlorphenamine, cyproheptadine, dimenhydrinate, diphenhydramine, doxylamine, mepyramine (pyrilamine), phenindamine, pheniramine, promethazine, tripelennamine, triprolidine) Atropine Atropine methonitrate Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine, zotepine) Benactyzine Benzatropine (benztropine) Benzilylcholine mustard Benzydamine BIBN 99 Biperiden Bornaprine CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Caramiphen Cloperastine CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Dimethindene Dexetimide DIBD Dicyclomine (dicycloverine) Ditran EA-3167 EA-3443 EA-3580 EA-3834 Etanautine Etybenzatropine (ethybenztropine) Flavoxate Himbacine HL-031,120 Ipratropium bromide J-104,129 Hyoscyamine Mamba toxin 3 Mamba toxin 7 Mazaticol Mebeverine Methoctramine Metixene N-Ethyl-3-piperidyl benzilate N-Methyl-3-piperidyl benzilate Orphenadrine Otenzepad Oxybutynin PBID PD-102,807 PD-0298029 Phenglutarimide Phenyltoloxamine Pipenzolate bromide Pirenzepine Piroheptine Procyclidine Profenamine Revefenacin RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine (hyoscine) Sofpironium bromide Solifenacin Telenzepine Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine) Timepidium bromide Tiotropium bromide Tolterodine Tricyclic antidepressants (e.g., amitriptyline, butriptyline, clomipramine, desipramine, dosulepin (dothiepin), doxepin, imipramine, lofepramine, nortriptyline, protriptyline, trimipramine) Trihexyphenidyl Tripitamine Tropacine Tropatepine Tropicamide Typical antipsychotics (e.g., chlorpromazine, loxapine, thioridazine) WIN-2299 Xanomeline Zamifenacin

nACh	Nicotinic agonists: 5-HIAA A-84,543 A-366,833 A-582,941 A-867,744 ABT-202 ABT-418 ABT-560 ABT-894 Acetylcholine Altinicline Anabasine Anatoxin-a AR-R17779 Butinoline Butyrylcholine Carbachol Choline Cotinine Cytisine Decamethonium Desformylflustrabromine Dianicline Dimethylphenylpiperazinium Epibatidine Epiboxidine Ethanol Ethoxysebacylcholine EVP-4473 EVP-6124 Galantamine GTS-21 Ispronicline Ivermectin Levamisole Lobeline MEM-63,908 (RG-3487) Morantel Nicotine (tobacco) NS-1738 PHA-543,613 PHA-709,829 PNU-120,596 PNU-282,987 Pozanicline Rivanicline RJR-2429 Sazetidine A SB-206553 Sebacylcholine SIB-1508Y SIB-1553A SSR-180,711 Suberyldicholine Suxamethonium (succinylcholine) TC-1698 TC-1734 TC-1827 TC-2216 TC-5214 TC-5619 TC-6683 Tebanicline Tropisetron UB-165 Varenicline WAY-317,538 XY-4083 Nicotinic antagonists: 18-MAC 18-MC α-Neurotoxins (e.g., α-bungarotoxin, α-cobratoxin, α-conotoxin, many others) ABT-126 Alcuronium Allopregnanolone Amantadine Anatruxonium AQW051 Atracurium Barbiturates (e.g., pentobarbital, sodium thiopental) Bungarotoxins (e.g., α-bungarotoxin, κ-bungarotoxin) Bupropion Chandonium Chlorisondamine Cisatracurium Coclaurine Coronaridine Cyclopropane Dacuronium Decamethonium Dehydronorketamine Desflurane Dextromethorphan Dextropropoxyphene Dextrorphan Diadonium DHβE Dihydrochandonium Dimethyltubocurarine (metocurine) Dipyrandium Dizocilpine (MK-801) Doxacurium Encenicline Enflurane Esketamine Fazadinium Gallamine Halothane Hexafluronium Hexamethonium (benzohexonium) Hydroxybupropion Hydroxynorketamine Ibogaine Isoflurane Ketamine Kynurenic acid Laudexium (laudolissin) Levacetylmethadol Levomethadone Malouetine ME-18-MC Mecamylamine Memantine Methadone Methorphan (racemethorphan) Methyllycaconitine Metocurine Mivacurium Morphanol (racemorphan) Neramexane Nitrous oxide Norketamine Pancuronium bromide Pempidine Pentamine Pentolinium Phencyclidine Pipecuronium Progesterone Promegestone Radafaxine Rapacuronium Reboxetine Rocuronium Sevoflurane Surugatoxin Thiocolchicoside Toxiferine Tramadol Trimetaphan camsilate (trimethaphan camsylate) Tropeinium Tubocurarine Vanoxerine Vecuronium Xenon

Transporter ligands

CHT	Inhibitors: Hemicholinium-3 (hemicholine) Triethylcholine Enhancers: Coluracetam

VAChT	Inhibitors: Vesamicol

Enzyme modulators

ChAT	Inhibitors: 1-(-Benzoylethyl)pyridinium 2-(α-Naphthoyl)ethyltrimethylammonium 3-Chloro-4-stillbazole 4-(1-Naphthylvinyl)pyridine Acetylseco hemicholinium-3 Acryloylcholine AF64A B115 BETA CM-54,903 N,N-Dimethylaminoethylacrylate N,N-Dimethylaminoethylchloroacetate

AChE	Inhibitors: Reversible: Carbamates: Aldicarb Bendiocarb Bufencarb Caffeine Carbaryl Carbendazim Carbetamide Carbofuran Chlorbufam Chloropropham Ethienocarb Ethiofencarb Fenobucarb Fenoxycarb Formetanate Furadan Itopride Ladostigil Methiocarb Methomyl Miotine Oxamyl Phenmedipham Pinmicarb Pirimicarb Propamocarb Propham Propoxur; Stigmines: Distigmine bromide Eptastigmine Ganstigmine Neostigmine Phenserine Physostigmine Pyridostigmine bromide Quilostigmine Rivastigmine Terestigmine; Others: Acotiamide Ambenonium Donepezil Caffeine Edrophonium Galantamine Huperzine A Ipidacrine Minaprine Tacrine Zanapezil Irreversible: Organophosphates: Acephate Azinphos-methyl Bensulide Cadusafos Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Cyclosarin Demeton Demeton-S-methyl Diazinon Dichlorvos Dicrotophos Diisopropyl fluorophosphate Diisopropylphosphate Dimethoate Dioxathion Disulfoton EA-3148 Echothiophate Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fosthiazate GV Isofluorophate Isoxathion Malaoxon Malathion Methamidophos Methidathion Metrifonate Mevinphos Monocrotophos Naled Novichok agent Omethoate Oxydemeton-methyl Paraoxon Parathion Parathion-methyl Phorate Phosalone Phosmet Phoxim Pirimiphos-methyl Sarin Soman Tabun Tebupirimfos Temefos Terbufos Tetrachlorvinphos Tribufos Trichlorfon VE VG VM VR VX; Others: Demecarium Fasciculins (green mamba toxins) (1, 2, 3, 4) Onchidal (Onchidella binneyi) Reactivators: Asoxime Obidoxime Pralidoxime

BChE	Inhibitors: Cymserine Many of the AChE inhibitors listed above

Release modulators

Inhibitors	SNAP-25 inactivators: Botulinum toxin (A, C, E) VAMP inactivators: Botulinum toxin (B, D, F, G) Others: Bungarotoxins (β-bungarotoxin, γ-bungarotoxin)

Enhancers	LPHN agonists: α-Latrotoxin Others: Atracotoxin (e.g., robustoxin, versutoxin) Crotoxin

Others

Precursors / prodrugs	Adafenoxate Choline (lecithin) Citicoline Cyprodenate Dimethylethanolamine Glycerophosphocholine Meclofenoxate (centrophenoxine) Phosphatidylcholine Phosphatidylethanolamine Phosphorylcholine Pirisudanol

Cofactors	Acetic acid Acetylcarnitine Acetyl-coA Vitamin B₅

Histaminergics

Receptor
(ligands)

H₁	Agonists: 2-Pyridylethylamine Betahistine Histamine HTMT UR-AK49 Antagonists: First-generation: 4-Methyldiphenhydramine Alimemazine Antazoline Azatadine Bamipine Benzatropine (benztropine) Bepotastine Bromazine Brompheniramine Buclizine Captodiame Carbinoxamine Chlorcyclizine Chloropyramine Chlorothen Chlorphenamine Chlorphenoxamine Cinnarizine Clemastine Clobenzepam Clocinizine Cloperastine Cyclizine Cyproheptadine Dacemazine Decloxizine Deptropine Dexbrompheniramine Dexchlorpheniramine Dimenhydrinate Dimetindene Diphenhydramine Diphenylpyraline Doxylamine Embramine Etodroxizine Etybenzatropine (ethylbenztropine) Etymemazine Fenethazine Flunarizine Histapyrrodine Homochlorcyclizine Hydroxyethylpromethazine Hydroxyzine Isopromethazine Isothipendyl Meclozine Medrylamine Mepyramine (pyrilamine) Mequitazine Methafurylene Methapyrilene Methdilazine Moxastine Orphenadrine Oxatomide Oxomemazine Phenindamine Pheniramine Phenyltoloxamine Pimethixene Piperoxan Pipoxizine Promethazine Propiomazine Pyrrobutamine Talastine Thenalidine Thenyldiamine Thiazinamium Thonzylamine Tolpropamine Tripelennamine Triprolidine Second/third-generation: Acrivastine Alinastine Astemizole Azelastine Bamirastine Barmastine Bepiastine Bepotastine Bilastine Cabastinen Carebastine Cetirizine Clemastine Clemizole Clobenztropine Desloratadine Dorastine Ebastine Efletirizine Emedastine Epinastine Fexofenadine Flezelastine Ketotifen Latrepirdine Levocabastine Levocetirizine Linetastine Loratadine Mapinastine Mebhydrolin Mizolastine Moxastine Noberastine Octastine Olopatadine Perastine Pibaxizine Piclopastine Quifenadine (phencarol) Rocastine Rupatadine Setastine Sequifenadine (bicarphen) Talastine Temelastine Terfenadine Vapitadine Zepastine Non-generational: Atypical antipsychotics (e.g., aripiprazole, asenapine, clozapine, iloperidone, olanzapine, paliperidone, quetiapine, risperidone, ziprasidone, zotepine) Tetracyclic antidepressants (e.g., amoxapine, loxapine, maprotiline, mianserin, mirtazapine, oxaprotiline) Tricyclic antidepressants (e.g., amitriptyline, butriptyline, clomipramine, desipramine, dosulepin (dothiepin), doxepin, imipramine, iprindole, lofepramine, nortriptyline, protriptyline, trimipramine) Typical antipsychotics (e.g., chlorpromazine, flupenthixol, fluphenazine, loxapine, perphenazine, prochlorperazine, thioridazine, thiothixene) Unknown/unsorted: Belarizine Elbanizine Flotrenizine Napactadine Tagorizine Trelnarizine Trenizine

H₂	Agonists: Amthamine Betazole Dimaprit Histamine HTMT Impromidine UR-AK49 Antagonists: Bisfentidine Burimamide Cimetidine Dalcotidine Donetidine Ebrotidine Etintidine Famotidine Isolamtidine Lafutidine Lamtidine Lavoltidine (loxtidine) Lupitidine Metiamide Mifentidine Niperotidine Nizatidine Osutidine Oxmetidine Pibutidine Quisultazine (quisultidine) Ramixotidine Ranitidine Roxatidine Sufotidine Tiotidine Tuvatidine Venritidine Xaltidine Zolantidine

H₃	Agonists: α-Methylhistamine Cipralisant Histamine Imetit Immepip Immethridine Methimepip Proxyfan Antagonists: A-349,821 A-423,579 ABT-239 ABT-652 AZD5213 Betahistine Burimamide Ciproxifan Clobenpropit Conessine Enerisant GSK-189,254 Impentamine Iodophenpropit Irdabisant JNJ-5207852 MK-0249 NNC 38-1049 PF-03654746 Pitolisant SCH-79687 Thioperamide VUF-5681

H₄	Agonists: 4-Methylhistamine α-Methylhistamine Histamine OUP-16 VUF-8430 Antagonists: JNJ-7777120 Mianserin Thioperamide Toreforant VUF-6002

Transporter
(inhibitors)

VMATs

TAAR1 inactive	Amiodarone APP AZIK Bietaserpine Deserpidine Dihydrotetrabenazine Efavirenz GBR-12935 GZ-793A Ibogaine Ketanserin Lobeline Methoxytetrabenazine Reserpine Rose bengal SD-809 Tetrabenazine Valbenazine Vanoxerine (GBR-12909)

TAAR1 active	Amphetamine Methamphetamine MDMA Phenethylamine

Enzyme
(inhibitors)

HDC	Catechin Meciadanol Naringenin Tritoqualine

HNMT	Amodiaquine Diphenhydramine Harmaline Metoprine Quinacrine SKF-91,488 Tacrine

DAO	Pimagedine (aminoguanidine)

Others

Precursors	L -Histidine

Cofactors	Vitamin B₆

Tricyclics

Classes	Acridine Anthracene Dibenzazepine Dibenzocycloheptene Dibenzodiazepine Dibenzothiazepine Dibenzothiepin Dibenzoxazepine Dibenzoxepin Phenothiazine Pyridazinobenzoxazine Pyridinobenzodiazepine Thioxanthene

Antidepressants (TCAs and TeCAs)	7-OH-Amoxapine Amezepine Amineptine Amitriptyline Amitriptylinoxide Amoxapine Aptazapine Azepindole Azipramine Batelapine Butriptyline Cianopramine Ciclazindol Ciclopramine Cidoxepin Clomipramine Cotriptyline Cyanodothiepin Demexiptiline Depramine/Balipramine Desipramine Dibenzepin Dimetacrine Dosulepin/Dothiepin Doxepin Enprazepine Esmirtazapine Fantridone Fluotracen Hepzidine Homopipramol Imipramine Imipraminoxide Intriptyline Iprindole Ketipramine Litracen Lofepramine Losindole Loxapine Maprotiline Mariptiline Mazindol Melitracen Metapramine Mezepine Mianserin Mirtazapine Monometacrine Naranol Nitroxazepine Nortriptyline Noxiptiline Octriptyline Opipramol Oxaprotiline Pipofezine Pirandamine Propizepine Protriptyline Quinupramine Setiptiline/Teciptiline Spiroxepin Tandamine Tampramine Tianeptine Tienopramine Trimipramine

Antihistamines	Azatadine Clobenzepam Cyproheptadine Dacemazine Deptropine Desloratadine Epinastine Etymemazine Fenethazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Ketotifen Latrepirdine Loratadine Mebhydrolin Mequitazine Methdilazine Olopatadine Oxomemazine Phenindamine Pimethixene Promethazine Propiomazine Rupatadine Thiazinamium

Antipsychotics	Acetophenazine Alimemazine Amoxapine Asenapine Butaclamol Butaperazine Carfenazine (carphenazine) Carpipramine Chlorpromazine Chlorprothixene Ciclindole Citatepine Clocapramine Clomacran Clorotepine Clotiapine Clozapine Cyanothepin Doclothepin Docloxythepin Erizepine Flucindole Flumezapine Fluotracen Flupentixol Fluphenazine Gevotroline Homopipramol Isofloxythepin Levomepromazine/Methotrimeprazine Loxapine Maroxepin Meperathiepin Mesoridazine Metiapine Metitepine Metoxepin Mosapramine Naranol Octomethothepin Olanzapine Oxyclothepin Oxyprothepin Pentiapine Peradithiepin Perathiepin Perazine Perphenazine Periciazine Pinoxepin Piperacetazine Pipotiazine Piquindone Prochlorperazine Promazine Prothipendyl Quetiapine Savoxepin/Cipazoxapine Sulforidazine Tenilapine Thiethylperazine Thiopropazate Thioridazine Thiothixene Tilozepine Traboxopine Trifluoperazine Triflupromazine Trifluthepin Zotepine Zuclopenthixol

Anticonvulsants	Carbamazepine Dizocilpine Eslicarbazepine Eslicarbazepine acetate Etazepine Licarbazepine Oxcarbazepine Oxitriptyline Rispenzepine

Others	Adosopine Aminopromazine Atiprosin Beloxepin Carvedilol Cidoxepin Cyclobenzaprine Damotepine Darenzepine Elanzepine Methylene blue Monatepil Nuvenzepine Oxetorone Perlapine P7C3 Pinadoline Pirenzepine Pirolate Pitrazepin Pizotifen Profenamine Serazapine Siltenzepine Telenzepine Tipindole Tropatepine Zolenzepine

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Azatadine

See also

References