dotarizine

{{Short description|Calcium channel blocker used in the treatment of migraine}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 399974376

| IUPAC_name = 1-[diphenylmethyl]-4-[3-(2-phenyl-1,3-dioxolan-2-yl)propyl]piperazine

| image = Dotarizine.svg

| width = 220

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 84625-59-2

| ATC_prefix = none

| ATC_suffix =

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2106316

| ChEBI = 138033

| PubChem = 55285

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

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| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = IO7663S6D3

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 49929

| C=29 | H=34 | N=2 | O=2

| smiles = C1CN(CCN1CCCC2(OCCO2)C3=CC=CC=C3)C(C4=CC=CC=C4)C5=CC=CC=C5

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = LRMJAFKKJLRDLE-UHFFFAOYSA-N

| synonyms = Dotarizine

}}

Dotarizine is a drug used in the treatment of migraine,{{cite journal | vauthors = Ruiz-Nuño A, Villarroya M, Cano-Abad M, Rosado A, Balfagón G, López MG, García AG | title = Mechanisms of blockade by the novel migraine prophylactic agent, dotarizine, of various brain and peripheral vessel contractility | journal = European Journal of Pharmacology | volume = 411 | issue = 3 | pages = 289–99 | date = January 2001 | pmid = 11164387 | doi = 10.1016/S0014-2999(00)00897-9 }} which acts as a calcium channel blocker,{{cite journal | vauthors = Ruiz-Nuño A, Mayorgas I, Hernández-Guijo JM, Olivares R, García AG, Gandía L | title = Antimigraine dotarizine blocks P/Q Ca2+ channels and exocytosis in a voltage-dependent manner in chromaffin cells | journal = European Journal of Pharmacology | volume = 481 | issue = 1 | pages = 41–50 | date = November 2003 | pmid = 14637173 | doi = 10.1016/j.ejphar.2003.09.013 }} and also as an antagonist at the 5HT_2A receptor, and to a lesser extent at the 5HT_1A and 5HT_2C receptors.{{cite journal | vauthors = Farré M, Roset PN, Llorente M, Márquez M, Albet C, Pérez JA, Herrero E, Ortíz JA | display-authors = 6 | title = Clinical pharmacokinetics and tolerability of dotarizine in healthy subjects after single and multiple oral administration | journal = Methods and Findings in Experimental and Clinical Pharmacology | volume = 19 | issue = 5 | pages = 343–50 | date = June 1997 | pmid = 9379783 }}{{cite journal | vauthors = Montiel C, Herrero CJ, García-Palomero E, Renart J, García AG, Lomax RB | title = Serotonergic effects of dotarizine in coronary artery and in oocytes expressing 5-HT2 receptors | journal = European Journal of Pharmacology | volume = 332 | issue = 2 | pages = 183–93 | date = August 1997 | pmid = 9286620 | doi = 10.1016/S0014-2999(97)01073-X }} The anti-migraine action is thought to be due to its action as a vasodilator,{{cite journal | vauthors = Kuridze N, Gajkowska B, Czernicki Z, Jurkiewicz J, Cervos-Navarro J | title = The effect of Dotarizine--(Ca2+ channel blocker)--on vascular reactivity and ultrastructure of cerebral capillaries in animals subjected to anoxia | journal = Folia Neuropathologica | volume = 36 | issue = 2 | pages = 101–8 | year = 1998 | pmid = 9757621 }}{{cite journal | vauthors = Kuridze N, Czernicki Z, Jarus-Dziedzic K, Jurkiewicz J, Cervos-Navarro J | title = Regional differences of cerebrovascular reactivity effected by calcium channel blocker - dotarizine | journal = Journal of the Neurological Sciences | volume = 175 | issue = 1 | pages = 13–6 | date = April 2000 | pmid = 10785251 | doi = 10.1016/S0022-510X(00)00275-6 | s2cid = 30117433 }} but it also has some anxiolytic effects{{cite journal | vauthors = Petkov VD, Belcheva S, Konstantinova E | title = Anxiolytic effects of dotarizine, a possible antimigraine drug | journal = Methods and Findings in Experimental and Clinical Pharmacology | volume = 17 | issue = 10 | pages = 659–68 | date = December 1995 | pmid = 9053586 }} and blocks amnesia produced by electroconvulsive shock in animals.{{cite journal | vauthors = Lazarova M, Petkova B, Petkov VD | title = Effect of dotarizine on electroconvulsive shock or pentylenetetrazol-induced amnesia and on seizure reactivity in rats | journal = Methods and Findings in Experimental and Clinical Pharmacology | volume = 17 | issue = 1 | pages = 53–8 | year = 1995 | pmid = 7623521 }}