Chemistry:Dotarizine

Dotarizine
Clinical data
Other names	Dotarizine
ATC code	none;
Identifiers
	IUPAC name 1-[diphenylmethyl]-4-[3-(2-phenyl-1,3-dioxolan-2-yl)propyl]piperazine;
CAS Number	84625-59-2 ;
PubChem CID	55285;
ChemSpider	49929 ;
UNII	IO7663S6D3;
ChEBI	CHEBI:138033;
ChEMBL	ChEMBL2106316 ;
Chemical and physical data
Formula	C29H34N2O2
Molar mass	442.603 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CN(CCN1CCCC2(OCCO2)C3=CC=CC=C3)C(C4=CC=CC=C4)C5=CC=CC=C5;
	InChI InChI=1S/C29H34N2O2/c1-4-11-25(12-5-1)28(26-13-6-2-7-14-26)31-21-19-30(20-22-31)18-10-17-29(32-23-24-33-29)27-15-8-3-9-16-27/h1-9,11-16,28H,10,17-24H2 ; Key:LRMJAFKKJLRDLE-UHFFFAOYSA-N ;
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Short description: Calcium channel blocker used in the treatment of migraine

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

↑ "Mechanisms of blockade by the novel migraine prophylactic agent, dotarizine, of various brain and peripheral vessel contractility". European Journal of Pharmacology 411 (3): 289–99. January 2001. doi:10.1016/S0014-2999(00)00897-9. PMID 11164387.
↑ "Antimigraine dotarizine blocks P/Q Ca2+ channels and exocytosis in a voltage-dependent manner in chromaffin cells". European Journal of Pharmacology 481 (1): 41–50. November 2003. doi:10.1016/j.ejphar.2003.09.013. PMID 14637173.
↑ "Clinical pharmacokinetics and tolerability of dotarizine in healthy subjects after single and multiple oral administration". Methods and Findings in Experimental and Clinical Pharmacology 19 (5): 343–50. June 1997. PMID 9379783.
↑ "Serotonergic effects of dotarizine in coronary artery and in oocytes expressing 5-HT2 receptors". European Journal of Pharmacology 332 (2): 183–93. August 1997. doi:10.1016/S0014-2999(97)01073-X. PMID 9286620.
↑ "The effect of Dotarizine--(Ca2+ channel blocker)--on vascular reactivity and ultrastructure of cerebral capillaries in animals subjected to anoxia". Folia Neuropathologica 36 (2): 101–8. 1998. PMID 9757621.
↑ "Regional differences of cerebrovascular reactivity effected by calcium channel blocker - dotarizine". Journal of the Neurological Sciences 175 (1): 13–6. April 2000. doi:10.1016/S0022-510X(00)00275-6. PMID 10785251.
↑ "Anxiolytic effects of dotarizine, a possible antimigraine drug". Methods and Findings in Experimental and Clinical Pharmacology 17 (10): 659–68. December 1995. PMID 9053586.
↑ "Effect of dotarizine on electroconvulsive shock or pentylenetetrazol-induced amnesia and on seizure reactivity in rats". Methods and Findings in Experimental and Clinical Pharmacology 17 (1): 53–8. 1995. PMID 7623521.

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Original source: https://en.wikipedia.org/wiki/Dotarizine. Read more

[1] "Mechanisms of blockade by the novel migraine prophylactic agent, dotarizine, of various brain and peripheral vessel contractility". European Journal of Pharmacology 411 (3): 289–99. January 2001. doi:10.1016/S0014-2999(00)00897-9. PMID 11164387.

[2] "Antimigraine dotarizine blocks P/Q Ca2+ channels and exocytosis in a voltage-dependent manner in chromaffin cells". European Journal of Pharmacology 481 (1): 41–50. November 2003. doi:10.1016/j.ejphar.2003.09.013. PMID 14637173.

[3] "Clinical pharmacokinetics and tolerability of dotarizine in healthy subjects after single and multiple oral administration". Methods and Findings in Experimental and Clinical Pharmacology 19 (5): 343–50. June 1997. PMID 9379783.

[4] "Serotonergic effects of dotarizine in coronary artery and in oocytes expressing 5-HT2 receptors". European Journal of Pharmacology 332 (2): 183–93. August 1997. doi:10.1016/S0014-2999(97)01073-X. PMID 9286620.

[5] "The effect of Dotarizine--(Ca2+ channel blocker)--on vascular reactivity and ultrastructure of cerebral capillaries in animals subjected to anoxia". Folia Neuropathologica 36 (2): 101–8. 1998. PMID 9757621.

[6] "Regional differences of cerebrovascular reactivity effected by calcium channel blocker - dotarizine". Journal of the Neurological Sciences 175 (1): 13–6. April 2000. doi:10.1016/S0022-510X(00)00275-6. PMID 10785251.

[7] "Anxiolytic effects of dotarizine, a possible antimigraine drug". Methods and Findings in Experimental and Clinical Pharmacology 17 (10): 659–68. December 1995. PMID 9053586.

[8] "Effect of dotarizine on electroconvulsive shock or pentylenetetrazol-induced amnesia and on seizure reactivity in rats". Methods and Findings in Experimental and Clinical Pharmacology 17 (1): 53–8. 1995. PMID 7623521.

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v t e Piperazines
Simple piperazines (no additional rings)	1-Cyclohexylpiperazine Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES
Phenylpiperazines	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 Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide Piberaline Piribedil 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 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 Azimilide Cinepazet Cinepazic acid Cinepazide Cyclohexylpiperazine EGIS-7625 Hexocyclium Indinavir JNJ-7777120 Lodenafil Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol

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