Etodroxizine

Chemical compound

None

Legal statusLegal status

BR: Class C1 (Other controlled substances)^[1]

Identifiers

IUPAC name

2-[2-(2-{4-[(4-Chlorophenyl)(phenyl)methyl]-1-piperazinyl}ethoxy)ethoxy]ethanol

CAS Number

17692-34-1

PubChem CID

63345

ChemSpider

57011

UNII

CI1S3XAK7O

ChEMBL

ChEMBL2104263

Chemical and physical dataFormulaC₂₃H₃₁ClN₂O₃Molar mass418.96 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

c1ccc(cc1)C(c2ccc(cc2)Cl)N3CCN(CC3)CCOCCOCCO

InChI

InChI=1S/C23H31ClN2O3/c24-22-8-6-21(7-9-22)23(20-4-2-1-3-5-20)26-12-10-25(11-13-26)14-16-28-18-19-29-17-15-27/h1-9,23,27H,10-19H2
Key:VUFOCTSXHUWGPW-UHFFFAOYSA-N

Etodroxizine (INN) (brand names Vesparax, Drimyl, Indunox, Isonox) is a first-generation antihistamine of the diphenylmethylpiperazine group which is used as a sedative/hypnotic drug in Europe and South Africa.^[2]^[3]^[4]^[5]

References

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 418–. ISBN 978-3-88763-075-1.
^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 1525–. ISBN 978-0-8155-1856-3.
^ Wolffgramm J, Lechner J, Coper H (1988). "Interaction of two barbiturates and an antihistamine on body temperature and motor performance of mice". Arzneimittelforschung. 38 (7): 885–91. PMID 2905131.
^ Maurer H, Pfleger K (1988). "Identification and differentiation of alkylamine antihistamines and their metabolites in urine by computerized gas chromatography-mass spectrometry". J Chromatogr. 430 (1): 31–41. doi:10.1016/s0378-4347(00)83131-x. PMID 2905706.

Hypnotics/sedatives (N05C)

GABA_A

Alcohols	2M2B Chloralodol Ethanol (alcohol) Diethylpropanediol Ethchlorvynol Methylpentynol Trichloroethanol
Barbiturates	Allobarbital Amobarbital Aprobarbital Barbital Butabarbital Butobarbital Cyclobarbital Ethallobarbital Heptabarb Hexobarbital Mephobarbital Methohexital Narcobarbital Pentobarbital Phenallymal Phenobarbital Propylbarbital Proxibarbal Reposal Secobarbital Talbutal Thiamylal Thiopental Thiotetrabarbital Vinbarbital Vinylbital
Benzodiazepines	Brotizolam Cinolazepam Climazolam Clonazolam Doxefazepam Estazolam Flubromazolam Flunitrazolam Flunitrazepam Flurazepam Flutoprazepam Lorazepam Loprazolam Lormetazepam Midazolam Nimetazepam Nitemazepam Nitrazepam Nitrazolam Quazepam Temazepam Triazolam
Carbamates	Carisoprodol Emylcamate Ethinamate Hexapropymate Meprobamate Methocarbamol Phenprobamate Procymate Tybamate
Imidazoles	Etomidate Metomidate Propoxate
Monoureides	Acecarbromal Apronal (apronalide) Bromisoval Capuride Carbromal Ectylurea
Neuroactive steroids	Acebrochol Allopregnanolone Alphadolone Alphaxolone Eltanolone Hydroxydione Minaxolone Progesterone
Nonbenzodiazepines	Eszopiclone Indiplon Lirequinil Necopidem Pazinaclone Saripidem Suproclone Suriclone Zaleplon Zolpidem Zopiclone
Phenols	Propofol
Piperidinediones	Glutethimide Methyprylon Pyrithyldione Piperidione
Quinazolinones	Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164
Others	Acetophenone Acetylglycinamide chloral hydrate Bromide compounds Lithium bromide Potassium bromide Sodium bromide Centalun Chloral betaine Chloral hydrate Chloralose Clomethiazole Dichloralphenazone Gaboxadol Kavalactones Loreclezole Paraldehyde Petrichloral Sulfonylalkanes Sulfonmethane (sulfonal) Tetronal Trional Triclofos Sesquiterpene Isovaleramide Isovaleric acid Valerenic acid

GABA_B

H₁

Antihistamines	Captodiame Cyproheptadine Diphenhydramine Doxylamine Hydroxyzine Methapyrilene Perlapine Pheniramine Promethazine Propiomazine
Antidepressants	Serotonin antagonists and reuptake inhibitors Etoperidone Nefazodone Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.
Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.

α₂-Adrenergic

5-HT_2A

Antidepressants	Trazodone Tricyclic antidepressants Amitriptyline Doxepin Trimipramine, etc. Tetracyclic antidepressants Mianserin Mirtazapine, etc.
Antipsychotics	Typical antipsychotics Chlorpromazine Thioridazine, etc. Atypical antipsychotics Olanzapine Quetiapine Risperidone, etc.
Others	Niaprazine

Melatonin

Orexin

α₂δ VDCC

Others

v t e Insomnia medications
GABA_A receptor positive modulators	Benzodiazepines: Brotizolam Cinolazepam Climazolam Clorazepate Doxefazepam Estazolam Etizolam Flunitrazepam Flurazepam Flutoprazepam Haloxazolam Loprazolam Lormetazepam Midazolam Nimetazepam Nitrazepam Quazepam Temazepam Triazolam Nonbenzodiazepines/Z-drugs: Eszopiclone Zaleplon Zolpidem Zopiclone Others: Alcohols (e.g., ethchlorvynol, amylene hydrate, ethanol) Barbiturates (e.g., amobarbital, pentobarbital, phenobarbital, secobarbital) Bromides (e.g., potassium bromide, sodium bromide) Carbamates (e.g., meprobamate) Chloral hydrate Clomethiazole Kava Neurosteroids (e.g., progesterone, zuranolone^†) Paraldehyde Piperidinediones (e.g., glutethimide) Quinazolinones (e.g., methaqualone) Sulfonmethane Valerian
Antihistamines (H₁ receptor inverse agonists)	Alimemazine Captodiame Dimenhydrinate Diphenhydramine Doxylamine Etodroxizine Hydroxyzine Meclizine Methapyrilene Pheniramine Phenyltoloxamine Pimethixene Promethazine Propiomazine Pyrilamine Tricyclic antidepressants (e.g., amitriptyline, doxepin, trimipramine) Tetracyclic antidepressants (e.g., mirtazapine) Triprolidine
Orexin receptor antagonists	Daridorexant Lemborexant Seltorexant^† Suvorexant
Melatonin receptor agonists	Melatonin Ramelteon Tasimelteon
Miscellaneous	Antipsychotics (e.g., quetiapine, olanzapine, risperidone, chlorpromazine) Ashwagandha Benzoctamine Cannabinoids (e.g., cannabis, dronabinol (THC), nabilone) Chamomile Fenadiazole Gabapentinoids (e.g., gabapentin, pregabalin, phenibut) Hops Lavender Menthyl isovalerate Niaprazine Opioids (e.g., hydrocodone, oxycodone, morphine) Passion flower Scopolamine Serotonin precursors (tryptophan, 5-HTPTooltip 5-hydroxytryptophan) Sodium oxybate (GHB) Sympatholytics (e.g., clonidine, guanfacine, prazosin) Theanine Trazodone Tricyclic antidepressants (e.g., amitriptyline, doxepin, trimipramine) Tetracyclic antidepressants (e.g., mirtazapine) Valnoctamide
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Histamine receptor modulators

H₁

Agonists

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
Perlapine
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

Others: Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, brilaroxazine, clozapine, iloperidone, olanzapine, paliperidone, quetiapine, risperidone, ziprasidone, zotepine)
Phenylpiperazine antidepressants (e.g., hydroxynefazodone, nefazodone, trazodone, triazoledione)
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: Azanator
Belarizine
Elbanizine
Flotrenizine
GSK1004723
Napactadine
Tagorizine
Trelnarizine
Trenizine

H₂

Agonists	Amthamine Betazole Dimaprit Histamine HTMT Impromidine L-Histidine 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 L-Histidine Methimepip Proxyfan
Antagonists	A-349821 A-423579 ABT-239 ABT-652 AZD5213 Bavisant Betahistine Burimamide Ciproxifan Clobenpropit Conessine Enerisant GSK-189254 Impentamine Iodophenpropit Irdabisant JNJ-5207852 NNC 38-1049 PF-03654746 Pitolisant SCH-79687 Thioperamide VUF-5681

H₄

Agonists	4-Methylhistamine α-Methylhistamine Histamine L-Histidine OUP-16 VUF-8430
Antagonists	JNJ-7777120 Mianserin Seliforant Thioperamide Toreforant VUF-6002

See also: Receptor/signaling modulators; Monoamine metabolism modulators; Monoamine reuptake inhibitors

v t e Piperazines
Simple piperazines (no additional rings)	Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES
Phenylpiperazines	2C-B-PP 3,4-CFP Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin CSP-2503 Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Fluanisone Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Naphthylpiperazine Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635
Benzylpiperazines	2C-B-BZP 3-Methylbenzylpiperazine Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide NSI-189 Piberaline Piribedil RN-1747 Sunifiram Trimetazidine Vesnarinone
Diphenylalkylpiperazines (benzhydrylalkylpiperazines)	AD-1211 Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenpipenol Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,783 GBR-12,935 GBR-13,069 GBR-13,098 GBR-13,119 Hydroxyzine Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine
Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Prazitone Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone
Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine ORG-12962 Pyridinylpiperazine
Benzo(iso)thiazolyl piperazines	Lurasidone Perospirone Revospirone Tiospirone Ziprasidone
Tricyclics (piperazine attached via side chain)	Amoxapine Clopenthixol Clorotepine Clozapine Cyanothepin Doclothepin Docloxythepin Flupentixol Fluphenazine Isofloxythepin Loxapine Meperathiepin Metitepine Octomethothepin Olanzapine Opipramol Oxyclothepin Oxyprothepin Peradithiepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Trifluthepin Zuclopenthixol
Others/Uncategorized	6-Nitroquipazine AP-238 Azimilide Bucinnazine Cinepazet Cinepazic acid Cinepazide CPD-1 Cyclohexylpiperazine EGIS-7625 Hexocyclium Indinavir JNJ-7777120 Lodenafil MK-212 Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol