Fanetizole

Fanetizole
Systematic (IUPAC) name

4-Phenyl-N-(2-phenylethyl)-1,3-thiazol-2-amine
Pharmacokinetic data
Protein binding	%
Identifiers
CAS Number	79069-94-6
PubChem	CID 54339
ChemSpider	49083
UNII	BH48F620JA^Y
Chemical data
Formula	C₁₇H₁₆N₂S
Molar mass	280.39 g/mol
SMILES n1c(csc1NCCc2ccccc2)c3ccccc3
InChI InChI=1S/C17H16N2S/c1-3-7-14(8-4-1)11-12-18-17-19-16(13-20-17)15-9-5-2-6-10-15/h1-10,13H,11-12H2,(H,18,19) Key:WEEYMMXMBFJUAI-UHFFFAOYSA-N
(verify)

Fanetizole shows immunoregulating activity.

Synthesis

Thioureas serve as a convenient starting material for 2-aminothiazoles.

Fanetizole synthesis:^[1]

Reaction of β-phenethylamine with ammonium isothiocyanate gives the thiourea (2) Treatment of that product with phenacyl bromide thus affords the thiazole product.

References

↑ Lombardino, J. G.; 1981, U.S. Patent 4,307,106

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 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 Rocastine Rupatadine Setastine 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 NBI-98854 Reserpine Rose bengal SD-809 Tetrabenazine 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	Aminoguanidine

Others

Precursors	L -Histidine

Cofactors	Vitamin B₆

Drugs for peptic ulcer and GERD/GORD (A02B)

H₂ antagonists ("-tidine")	Cimetidine Famotidine Lafutidine Lavoltidine (loxtidine) Niperotidine Nizatidine Ranitidine Roxatidine

Prostaglandins (E)/analogues ("-prost-")	Misoprostol Enprostil

Proton-pump inhibitors ("-prazole")	Dexlansoprazole Esomeprazole Ilaprazole Lansoprazole Omeprazole Pantoprazole Picoprazole Rabeprazole Tenatoprazole Timoprazole

Potassium-competitive acid blockers ("-prazan")	Linaprazan Revaprazan Soraprazan Vonoprazan

Other	Acetoxolone Alginic acid Arbaclofen placarbil Carbenoxolone Cetraxate Gefarnate Lesogaberan Pirenzepine Proglumide Rebamipide Sucralfate Sulglicotide Telenzepine Teprenone Troxipide Zolimidine

Combinations	Bismuth subcitrate/metronidazole/tetracycline

See also: Helicobacter pylori* eradication protocols*

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