Dotarizine: Wikis

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Dotarizine
Systematic (IUPAC) name

1-[diphenylmethyl]-4-[3-(2-phenyl-1,3-dioxolan-2-yl)propyl]piperazine
Identifiers
CAS number	84625-59-2
ATC code	none
PubChem	55285
Chemical data
Formula	C₂₉H₃₄N₂O₂
Mol. mass	442.592 g/mol
SMILES	eMolecules & PubChem
Synonyms	Dotarizine
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

Dotarizine is a drug used in the treatment of migraine,^[1] which acts as a calcium channel blocker,^[2] and also as an antagonist at the 5HT_2A receptor, and to a lesser extent at the 5HT_1A and 5HT_2C receptors.^[3]^[4] The anti-migraine action is thought to be due to its action as a vasodilator,^[5]^[6] but it also has some anxiolytic effects^[7] and blocks amnesia produced by electroconvulsive shock in animals.^[8]

References

^ Ruiz-Nuño A, Villarroya M, Cano-Abad M, Rosado A, Balfagón G, López MG, García AG. Mechanisms of blockade by the novel migraine prophylactic agent, dotarizine, of various brain and peripheral vessel contractility. European Journal of Pharmacology. 2001 Jan 12;411(3):289-99. PMID 11164387
^ Ruiz-Nuño A, Mayorgas I, Hernández-Guijo JM, Olivares R, García AG, Gandía L. Antimigraine dotarizine blocks P/Q Ca2+ channels and exocytosis in a voltage-dependent manner in chromaffin cells. European Journal of Pharmacology. 2003 Nov 14;481(1):41-50. PMID 14637173
^ Farré M, Roset PN, Llorente M, Márquez M, Albet C, Pérez JA, Herrero E, Ortíz JA. Clinical pharmacokinetics and tolerability of dotarizine in healthy subjects after single and multiple oral administration. Methods and Findings in Experimental and Clinical Pharmacology. 1997 Jun;19(5):343-50. PMID 9379783
^ Montiel C, Herrero CJ, García-Palomero E, Renart J, García AG, Lomax RB. Serotonergic effects of dotarizine in coronary artery and in oocytes expressing 5-HT2 receptors. European Journal of Pharmacology. 1997 Aug 6;332(2):183-93. PMID 9286620
^ Kuridze N, Gajkowska B, Czernicki Z, Jurkiewicz J, Cervos-Navarro J. The effect of Dotarizine--(Ca2+ channel blocker)--on vascular reactivity and ultrastructure of cerebral capillaries in animals subjected to anoxia. Folia Neuropathologica. 1998;36(2):101-8. PMID 9757621
^ Kuridze N, Czernicki Z, Jarus-Dziedzic K, Jurkiewicz J, Cervos-Navarro J. Regional differences of cerebrovascular reactivity effected by calcium channel blocker - dotarizine. Journal of Neurological Sciences. 2000 Apr 1;175(1):13-6. PMID 10785251
^ Petkov VD, Belcheva S, Konstantinova E. Anxiolytic effects of dotarizine, a possible antimigraine drug. Methods and Findings in Experimental and Clinical Pharmacology. 1995 Dec;17(10):659-68. PMID 9053586
^ Lazarova M, Petkova B, Petkov VD. Effect of dotarizine on electroconvulsive shock or pentylenetetrazol-induced amnesia and on seizure reactivity in rats. Methods and Findings in Experimental and Clinical Pharmacology. 1995 Jan-Feb;17(1):53-8. PMID 7623521

Antimigraine preparations (N02C)

Analgesic/abortive

Serotonin modulators

Ergot alkaloids	Dihydroergotamine • Ergotamine • Methysergide • Lisuride

5-HT1 agonists	Triptans (Almotriptan, Eletriptan, Frovatriptan, Naratriptan, Rizatriptan, Sumatriptan, Zolmitriptan) Alniditan

Other	Dotarizine

Other

Paracetamol^# • Amidrine

Prevention of migraines

beta blocker (Propranolol^#) • calcium channel blocker (Verapamil) • corticosteroid (Flumedroxone) • monosaccharide (Topiramate) • adrenergic agonist (Clonidine)

Ungrouped

piperidine (Pizotifen) • adrenochrome (Iprazochrome) • phenothiazine (Dimetotiazine) • benzoxepin (Oxetorone) • piperazine (Lomerizine) • azepine (Telcagepant)

^#WHO-EM. ^‡Withdrawn from market. CLINICAL TRIALS: ^†Phase III. ^§Never to phase III

Serotonergics

Receptor
ligands

5-HT₁

5-HT_1A	Agonists: Azapirones: Alnespirone • Binospirone • Buspirone • Eptapirone • Gepirone • Ipsapirone • Perospirone • Tandospirone • Tiospirone • Zalospirone; Lysergamides: Dihydroergotamine • Ergotamine • Methysergide • LSD; Piperazines: Eltoprazine • Flesinoxan • Flibanserin; Tryptamines: 5-CT • 5-MeO-DMT • 5-MT • DMT • Psilocin • Psilocybin; Atypical Antipsychotics: Aripiprazole • Asenapine • Clozapine • Quetiapine • Ziprasidone; Others: 8-OH-DPAT • Befiradol • F-11440 • Lesopitron • Lu AA21004 • LY-293,284 • LY-301,317 • MKC-242 • N-Dealkyloxaflozane • Osemozotan • Oxaflozane • Piclozotan • PRX-00023 • Rauwolscine • Repinotan • RU-24969 • S-15535 • Sarizotan • SSR-181,507 • Sunepitron • U-92016A • Urapidil • Vilazodone • Xaliproden • Yohimbine Antagonists: Beta Blockers: Alprenolol • Cyanopindolol • Iodocyanopindolol • Oxprenolol • Pindobind • Pindolol • Propranolol; Piperazines: Etoperidone • Nefazodone • Trazodone • WAY-100,135 • WAY-100,635; Others: AV965 • BMY-7378 • Dotarizine • Flopropione • GR-46611 • Isamoltane • Lecozotan • Metitepine/Methiothepin • MPPF • NAN-190 • Robalzotan • S-15535 • SB-649915 • SDZ 216-525 • Spiperone • Spiramide • Spiroxatrine • UH-301 • WAY-100,135 • WAY-100,635 • Xylamidine

5-HT_1B	Agonists: Lysergamides: Dihydroergotamine • Ergotamine • Methysergide; Piperazines: Eltoprazine • TFMPP; Triptans: Eletriptan • Sumatriptan • Zolmitriptan; Tryptamines: 5-CT • 5-MT; Others: CGS-12066A • CP-93,129 • CP-94,253 • CP-135,807 • RU-24969 Antagonists: Lysergamides: Metergoline; Others: AR-A000002 • GR-127,935 • Isamoltane • Metitepine/Methiothepin • SB-216,641 • SB-224,289 • SB-236,057 • Yohimbine

5-HT_1D	Agonists: Lysergamides: Dihydroergotamine • Methysergide; Triptans: Almotriptan • Eletriptan • Frovatriptan • Naratriptan • Rizatriptan • Sumatriptan • Zolmitriptan; Tryptamines: 5-CT • 5-MT; Others: CP-135,807 • CP-286,601 • GR-46611 • L-694,247 • L-772,405 • PNU-109,291 • PNU-142,633 Antagonists: Lysergamides: Metergoline; Others: Alniditan BRL-15572 • GR-127,935 • Ketanserin • LY-310,762 • LY-367,642 • LY-456,219 • LY-456,220 • Metitepine/Methiothepin • Ritanserin • Yohimbine • Ziprasidone

5-HT_1E	Agonists: Lysergamides: Methysergide; Triptans: Eletriptan; Tryptamines: Tryptamine Antagonists: Metitepine/Methiothepin

5-HT_1F	Agonists: Triptans: Eletriptan • Naratriptan • Sumatriptan; Tryptamines: 5-MT; Others: LY-334,370 Antagonists: Metitepine/Methiothepin

5-HT₂

5-HT_2A	Agonists: Lysergamides: ALD-52 • Ergonovine • Lisuride • LA-SS-Az • LSD • Lysergic acid 2-butyl amide • Methysergide; Phenethylamines: 25I-NBMD • 25I-NBOH • 25I-NBOMe • 2C-B • 2C-B-FLY • 2C-E • 2C-I • 2C-T-2 • 2C-T-7 • 2C-T-21 • 2CBCB-NBOMe • 2CBFly-NBOMe • Bromo-DragonFLY • DOB • DOC • DOI • DOM • MDA • MDMA • Mescaline • Myristicin • TCB-2 • TFMFly; Piperazines: BZP • Quipazine • TFMPP; Tryptamines: 5-CT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT • 5-MT • α-ET • α-Methyl-5-HT • α-MT • Bufotenin • DET • DiPT • DMT • DPT • Psilocin • Psilocybin; Others: AL-34662 • AL-37350A• Medifoxamine • N-Dealkyloxaflozane • Oxaflozane • PNU-22394 Antagonists: Atypical Antipsychotics: Amperozide • Aripiprazole • Clozapine • Iloperidone • Melperone • Olanzapine • Paliperidone • Pimozide • Quetiapine • Risperidone • Sertindole • Ziprasidone • Zotepine; Typical Antipsychotics: Loxapine • Pipamperone; Antidepressants: Amitriptyline • Amoxapine • Etoperidone • Mianserin • Mirtazapine • Nefazodone • Trazodone; Others: 5-I-R91150 • AC-90179 • Altanserin • AMDA • APD-215 • Blonanserin • Cinanserin • Cyproheptadine • Deramciclane • Dotarizine • Eplivanserin • Fananserin • Flibanserin • Ketanserin • KML-010 • Lubazodone • Metitepine/Methiothepin • Nantenine • Pimavanserin • Pizotifen • Rauwolscine • Ritanserin • Sarpogrelate • Setoperone • Spiperone • Spiramide • SR-46349B • Volinanserin • Xylamidine • Yohimbine

5-HT_2B	Agonists: Oxazolines: 4-Methylaminorex • Aminorex; Phenethylamines: Chlorphentermine • DOB • DOC • DOI • DOM • Fenfluramine • MDA • MDMA • Norfenfluramine; Tryptamines: 5-CT • 5-MT • α-Methyl-5-HT; Others: BW-723C86 • Cabergoline • mCPP • Pergolide • PNU-22394 • Ro60-0175 Antagonists: Agomelatine • Asenapine • EGIS-7625 • Ketanserin • Lisuride • LY-272,015 • Metitepine/Methiothepin • Rauwolscine • Ritanserin • RS-127,445 • Sarpogrelate • SB-200,646 • SB-204,741 • SB-206,553 • SB-215,505 • SB-221,284 • SB-228,357 • SDZ SER-082 • Tegaserod • Yohimbine

5-HT_2C	Agonists: Phenethylamines: 2C-B • 2C-E • 2C-I • 2C-T-2 • 2C-T-7 • 2C-T-21 • DOB • DOC • DOI • DOM • MDA • MDMA • Mescaline • Myristicin; Piperazines: Aripiprazole • mCPP • TFMPP; Tryptamines: 5-CT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT • 5-MT • α-ET • α-Methyl-5-HT • α-MT • Bufotenin • DET • DiPT • DMT • DPT • Psilocin • Psilocybin; Others: A-372,159 • AL-38022A • CP-809,101 • Lorcaserin• Medifoxamine • MK-212 • N-Dealkyloxaflozane • ORG-37,684 • Oxaflozane • PNU-22394 • Ro60-0175 • Vabicaserin • WAY-629 • WAY-161,503 • YM-348 Antagonists: Atypical Antipsychotics: Clozapine • Iloperidone • Melperone • Olanzapine • Paliperidone • Pimozide • Quetiapine • Risperidone • Sertindole • Ziprasidone • Zotepine; Typical Antipsychotics: Chlorpromazine • Loxapine • Pipamperone; Antidepressants: Agomelatine • Amitriptyline • Amoxapine • Etoperidone • Fluoxetine • Mianserin • Mirtazapine • Nefazodone • Nortriptyline • Trazodone; Others: Cinanserin • Cyproheptadine • Deramciclane • Dimebolin • Dotarizine • Eltoprazine • FR-260,010 • Ketanserin • Ketotifen • Metitepine/Methiothepin • Methysergide • Pizotifen • Ritanserin • RS-102,221 • SB-200,646 • SB-206,553 • SB-221,284 • SB-228,357 • SB-242,084 • SB-243,213 • SDZ SER-082 • Xylamidine

5-HT₃

Agonists: Piperazines: BZP • Quipazine; Tryptamines: 2-Methyl-5-HT • 5-CT; Others: Chlorophenylbiguanide • RS-56812 • SR-57,227 • SR-57,227-A • YM-31636
Antagonists: Antiemetics: AS-8112 • Alosetron • Azasetron • Batanopride • Bemesetron • Cilansetron • Dolasetron • Granisetron • Lerisetron • Ondansetron • Palonosetron • Ramosetron • Renzapride • Tropisetron • Zacopride • Zatosetron; Atypical Antipsychotics: Clozapine • Olanzapine • Quetiapine; Tetracyclic Antidepressants: Amoxapine • Mianserin • Mirtazapine; Others: ICS-205,930 • Lu AA21004 • MDL-72,222 • Memantine • Ricasetron

5-HT₄

Agonists: Gastroprokinetic Agents: Cisapride • Metoclopramide • Mosapride • Prucalopride • Renzapride • Tegaserod • Zacopride; Others: 5-MT • BIMU-8 • CJ-033,466 • PRX-03140 • RS-67333 • RS-67506 • TD-5108
Antagonists: GR-113,808 • GR-125,487 • L-Lysine • Piboserod • RS-39604 • RS-67532 • SB-203,186

5-HT₅

5-HT_5A	Agonists: Lysergamides: Ergotamine • LSD; Tryptamines: 5-CT; Others: Valerenic Acid Antagonists: Asenapine • Dimebolin • Metitepine/Methiothepin • Ritanserin • SB-699,551

5-HT_5B*	Agonists: Lysergamides: Ergotamine • LSD Antagonists: Metitepine/Methiothepin * Note that the 5-HT_5B receptor is not functional in humans.

5-HT₆

Agonists: Lysergamides: Lisuride • LSD • Metergoline; Tryptamines: 5-CT • 5-MT • E-6801 • E-6837 • EMD-386,088 • EMDT • LY-586,713 • WAY-181,187 • WAY-208,466
Antagonists: Antidepressants: Amitriptyline • Amoxapine • Clomipramine • Doxepin • Mianserin • Nortriptyline; Atypical Antipsychotics: Aripiprazole • Asenapine • Clozapine • Fluperlapine • Iloperidone • Olanzapine • Tiospirone; Typical Antipsychotics: Chlorpromazine • Loxapine; Others: BGC20-760 • BVT-5182 • BVT-74316 • Dimebolin • EGIS-12233 • GW-742,457 • Ketanserin • Metitepine/Methiothepin • MS-245 • PRX-07034 • Ritanserin • Ro 04-6790 • Ro 63-0563 • SB-258,585 • SB-271,046 • SB-357,134 • SB-399,885

5-HT₇

Agonists: Lysergamides: LSD; Tryptamines: 5-CT • 5-MT; Others: 8-OH-DPAT • AS-19 • Bifeprunox • LP-12 • LP-44 • Sarizotan
Antagonists: Antidepressants: Amitriptyline • Amoxapine • Clomipramine • Imipramine • Maprotiline • Mianserin; Atypical Antipsychotics: Amisulpride • Aripiprazole • Clozapine • Olanzapine • Risperidone • Sertindole • Tiospirone • Ziprasidone • Zotepine; Typical Antipsychotics: Chlorpromazine • Loxapine; Others: EGIS-12233 • LY-215,840 • Mesulergine • Metergoline • Metitepine/Methiothepin • Pimozide • Ritanserin • SB-258,719 • SB-258,741 • SB-269,970 • SB-656,104 • SB-656,104-A • SB-691,673 • SLV-313 • SLV-314 • Spiperone • SSR-181,507

Reuptake
inhibitors

Plasmalemmal

SERT inhibitors	Selective Serotonin Reuptake Inhibitors (SSRIs): Alaproclate • Citalopram • Dapoxetine • Desmethylcitalopram • Desmethylsertraline • Elzasonan • Escitalopram • Femoxetine • Fluoxetine • Fluvoxamine • Indalpine • Litoxetine • Lubazodone • Norfluoxetine • Paroxetine • RTI-353 • Sertraline • Vilazodone • Zimelidine; Serotonin-Norepinephrine Reuptake Inhibitors (SNRIs): Bicifadine • Desvenlafaxine • Duloxetine • Milnacipran • Venlafaxine; Serotonin-Norepinephrine-Dopamine Reuptake Inhibitors (SNDRIs): Brasofensine • Diclofensine • DOV-102,677 • DOV-21,947 • DOV-216,303 • NS-2359 • SEP-225,289 • SEP-227,162 • Tesofensine; Tricyclic Antidepressants (TCAs): Amitriptyline • Butriptyline • Cianopramine • Clomipramine • Desipramine • Dosulepin • Doxepin • Imipramine • Lofepramine • Nortriptyline • Protriptyline • Trimipramine; Tetracyclic Antidepressants (TeCAs): Amoxapine; Piperazines: Nefazodone • Trazodone; Antihistamines: Brompheniramine • Chlorpheniramine • Diphenhydramine • Mepyramine (Pyrilamine) • Pheniramine • Tripelennamine; Opioids: Meperidine (Pethidine) • Methadone • Propoxyphene; Others: Cocaine • Cyclobenzaprine (CBZ) • Dextromethorphan (DXM) • Mesembrine • Nefopam • SB-649,915 • Sibutramine • Ziprasidone

TRPC6 activators	Adhyperforin • Hyperforin

Vesicular

VMAT Inhibitors

Ibogaine • Reserpine • Tetrabenazine

Releasing
agents

Enzyme
inhibitors

Anabolism

TPH inhibitors	AGN-2979 • Fenclonine

AAAD inhibitors	Benserazide • Carbidopa

Catabolism

MAO Inhibitors

Nonselective: Benmoxin • Furazolidone • Hydralazine • Iproclozide • Iproniazid • Isocarboxazid • Isoniazid • Linezolid • Mebanazine • Metfendrazine • Nialamide • Octamoxin • Phenelzine • Pheniprazine • Phenoxypropazine • Pivalylbenzhydrazine • Procarbazine • Safrazine • Tranylcypromine; MAO-A Selective: Befloxatone • Brofaromine • Cimoxatone • Clorgiline • Harmala alkaloids (Harmine, Harmaline, Tetrahydroharmine, Harman, Norharman, etc) • Metralindole • Minaprine • Moclobemide • Pirlindole • Toloxatone • Tyrima

Others

Precursors	L-Tryptophan → 5-HTP

Cofactors	Ferrous iron (Fe²⁺) • Magnesium (Mg²⁺) • Tetrahydrobiopterin • Vitamin B3 (Niacin, Nicotinamide → NADPH) • Vitamin B6 (Pyridoxine, Pyridoxamine, Pyridoxal → Pyridoxal phosphate) • Vitamin B9 (Folic Acid → Tetrahydrofolic acid) • Vitamin C (Ascorbic acid) • Zinc (Zn²⁺)

Others	Activity enhancers: Benzofuranylpropylaminopentane (BPAP) • Phenylpropylaminopentane (PPAP); Reuptake enhancers: Tianeptine

Piperazines

1-Cyclohexylpiperazine • 2C-B-BZP • Acaprazine • Almitrine • Alnespirone • Aminoethylpiperazine • Amoxapine • Antrafenine • Aripiprazole • Atevirdine • Azaperone • Azimilide • Befuraline • Bifeprunox • Binospirone • BRL-15572 • Buclizine • Buspirone • BZP • Chlorbenzoxamine • Chlorcyclizine • Cinepazet • Cinnarizine • Ciprofloxacin • Clocinizine • Clopenthixol • Clozapine • CPPene • Cyclizine • Dasatinib • DBL-583 • DBZP • Dibenzylpiperazine • Diethylcarbamazine • Dimethylphenylpiperazinium • Dotarizine • DPI-3290 • Dropropizine • EGIS-12233 • Eltoprazine • Ensaculin • Etoperidone • Fipexide • Flesinoxan • Flibanserin • Flupentixol • Fluphenazine • Fluprazine • GBR-12935 • Gepirone • HEPPS • Hexocyclium • Hydroxyzine • Imatinib • Indinavir • Ipsapirone • Itraconazole • JNJ-7777120 • Ketoconazole • Levodropropizine • Lidoflazine • Loxapine • Lurasidone • Manidipine • MBZP • mCPP • MDBZP • Meclizine • MeOPP • Nefazodone • Niaprazine • Olanzapine • Opipramol • Oxatomide • Oxypertine • PB28 • Perazine • Perospirone • Perphenazine • pFPP • Piberaline • Piperazine • PIPES • Pirenzepine • Piribedil • Posaconazole • Prochlorperazine • PRX-00023 • Quipazine • Ranolazine • S-15535 • SA 4503 • SB-258,585 • SB-271,046 • SB-357,134 • SB-399,885 • Sildenafil • Tandospirone • TFMPP • Thiethylperazine • Thiothixene • Tirilazad • Trazodone • Trelibet • Trifluoperazine • Trimazosin • Trimetazidine • Vanoxerine • Vardenafil • Vesnarinone • Vilazodone • VUF-6002 • WAY-100,135 • WAY-100,635 • Zalospirone • Zipeprol • Ziprasidone • Zuclopenthixol

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