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MedKoo Cat#: 413906 | Name: Dotarizine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dotarizine is a calcium channel blocker with antihistaminic properties, primarily investigated for the prophylactic treatment of migraine. It acts by inhibiting the influx of calcium ions into vascular smooth muscle and neurons, which helps reduce neurovascular inflammation and vasodilation associated with migraine attacks. Dotarizine also exhibits serotonin receptor antagonism (notably at 5-HT₂ receptors), further contributing to its antimigraine effects.

Chemical Structure

Dotarizine
Dotarizine
CAS#84625-59-2

Theoretical Analysis

MedKoo Cat#: 413906

Name: Dotarizine

CAS#: 84625-59-2

Chemical Formula: C29H34N2O2

Exact Mass: 442.2620

Molecular Weight: 442.60

Elemental Analysis: C, 78.70; H, 7.74; N, 6.33; O, 7.23

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Synonym
Dotarizina; Dotarizine; Dotarizinum
IUPAC/Chemical Name
1-(Diphenylmethyl)-4-(3-(2-phenyl-1,3-dioxolan-2-yl)propyl)piperazine
InChi Key
LRMJAFKKJLRDLE-UHFFFAOYSA-N
InChi Code
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
SMILES Code
N1(C(C2=CC=CC=C2)C3=CC=CC=C3)CCN(CCCC4(C5=CC=CC=C5)OCCO4)CC1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Dotarizine is a 5-HT2 receptor antagonist.
In vitro activity:
The mechanism of blockade of P/Q Ca(2+) channels by antimigraine, dotarizine, was studied in voltage-clamped bovine adrenal chromaffin cells. Inward currents through P/Q channels were pharmacologically isolated by superfusing the cells with omega-conotoxin GVIA (1 microM) plus nifedipine (3 microM). Dotarizine (10-30 microM) blocked the P/Q fraction of I(Ba) and promoted current inactivation. Thus, dotarizine caused a greater blockade of the late I(Ba), compared with blockade of the early peak I(Ba). Reference: Eur J Pharmacol. 2003 Nov 14;481(1):41-50. https://pubmed.ncbi.nlm.nih.gov/14637173/
In vivo activity:
These data reveal a decrease of antivasoconstrictive properties of Dotarizine between its administration and vasoconstrictive test. Thus Dotarizine might be useful as prophylactic medication in migraine therapy, due to its Ca2+ channel blocking and antiserotoninergic properties, but the time-frame of its efficacy has to be defined. Reference: Neurol Res. 2000 Mar;22(2):229-32. https://pubmed.ncbi.nlm.nih.gov/10763515/

Preparing Stock Solutions

The following data is based on the product molecular weight 442.60 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. 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. Eur J Pharmacol. 2003 Nov 14;481(1):41-50. doi: 10.1016/j.ejphar.2003.09.013. PMID: 14637173. 2. 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. Eur J Pharmacol. 2001 Jan 12;411(3):289-99. doi: 10.1016/s0014-2999(00)00897-9. PMID: 11164387. 3. Kuridze N, Czernicki Z, Jarus-Dziedzic K, Jurkiewicz J, Cervos-Navarro J. Vasostabilizing effect of Dotarizine (Ca(2+)-channel blocker) on cerebrovascular reactivity in rabbits. Neurol Res. 2000 Mar;22(2):229-32. doi: 10.1080/01616412.2000.11740664. PMID: 10763515. 4. Jarus-Dziedzic K, Czernicki Z, Cervos-Navarro J, Jurkiewicz J. Effect of oral administration of dotarizine on cerebrovasculature subjected to constriction followed by dilatation in rabbits. Acta Neurochir (Wien). 1999;141(11):1209-12. doi: 10.1007/s007010050420. PMID: 10592122.
In vitro protocol:
1. 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. Eur J Pharmacol. 2003 Nov 14;481(1):41-50. doi: 10.1016/j.ejphar.2003.09.013. PMID: 14637173. 2. 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. Eur J Pharmacol. 2001 Jan 12;411(3):289-99. doi: 10.1016/s0014-2999(00)00897-9. PMID: 11164387.
In vivo protocol:
1. Kuridze N, Czernicki Z, Jarus-Dziedzic K, Jurkiewicz J, Cervos-Navarro J. Vasostabilizing effect of Dotarizine (Ca(2+)-channel blocker) on cerebrovascular reactivity in rabbits. Neurol Res. 2000 Mar;22(2):229-32. doi: 10.1080/01616412.2000.11740664. PMID: 10763515. 2. Jarus-Dziedzic K, Czernicki Z, Cervos-Navarro J, Jurkiewicz J. Effect of oral administration of dotarizine on cerebrovasculature subjected to constriction followed by dilatation in rabbits. Acta Neurochir (Wien). 1999;141(11):1209-12. doi: 10.1007/s007010050420. PMID: 10592122.
1: Villarroya M, Gandía L, Lara B, Albillos A, López MG, García AG. Dotarizine versus flunarizine as calcium antagonists in chromaffin cells. Br J Pharmacol. 1995 Jan;114(2):369-76. doi: 10.1111/j.1476-5381.1995.tb13236.x. PMID: 7881736; PMCID: PMC1510232. 2: Novalbos J, Abad-Santos F, Zapater P, Cano-Abad MF, Moradiellos J, Sánchez- García P, García AG. Effects of dotarizine and flunarizine on chromaffin cell viability and cytosolic Ca2+. Eur J Pharmacol. 1999 Feb 5;366(2-3):309-17. doi: 10.1016/s0014-2999(98)00916-9. PMID: 10082213. 3: 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. Eur J Pharmacol. 1997 Aug 6;332(2):183-93. doi: 10.1016/s0014-2999(97)01073-x. PMID: 9286620. 4: 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. Eur J Pharmacol. 2003 Nov 14;481(1):41-50. doi: 10.1016/j.ejphar.2003.09.013. PMID: 14637173. 5: Cartheuser CF, Brasó A, Sacristán A, Ortiz JA. Effects of dotarizine on peripheral and pulmonary circulation and cardiac dynamics in dogs. Pharmacology. 1994 Mar;48(3):187-93. doi: 10.1159/000139178. PMID: 8153146. 6: Hadjiivanova C, Petkov VD, Maslarov D, Totev A, Panova Y, Belcheva I. Effect of dotarizine on K(+)-stimulated [3H]-serotonin and [3H]-acetylcholine release from rat hippocampus. Gen Pharmacol. 1997 Jan;28(1):129-32. doi: 10.1016/s0306-3623(96)00177-2. PMID: 9112089. 7: Onal MB, Solmaz I, Civelek E, Kircelli A, Tehli O, Izci Y, Erdogan E, Gonul E. Comparison of intrathecal dotarizine and nimodipine treatments in cerebral vasospasm after subarachnoid hemorrhage: an experimental study in rabbits. Acta Neurochir Suppl. 2011;110(Pt 2):55-60. doi: 10.1007/978-3-7091-0356-2_11. PMID: 21125446. 8: 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. Eur J Pharmacol. 2001 Jan 12;411(3):289-99. doi: 10.1016/s0014-2999(00)00897-9. PMID: 11164387. 9: Perelló E, Esteller E, Colls A, Magriñá C, Massegur H, Lluansí J, Casamitjana JF, Lao X, Roca-Ribas F, Miró N, Prades J, Herrero E, Molá O, Torres J, Márquez M, Ortiz JA. Eficacia y seguridad de dotarizina frente a cinarizina en el tratamiento sintomático de los trastornos agudos del equilibrio (vértigo común) [Efficacy and safety of dotarizine vs. cinnarizine in the symptomatic treatment of acute balance disorders (common vertigo)]. An Otorrinolaringol Ibero Am. 1998;25(3):291-310. Spanish. PMID: 9658668. 10: Tejerina T, Chulia T, Gonzalez P. Effects of dotarizine on 45Ca2+ movements and contractile responses in vascular smooth muscle. Eur J Pharmacol. 1993 Aug 3;239(1-3):75-81. doi: 10.1016/0014-2999(93)90978-q. PMID: 8223916. 11: 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 Find Exp Clin Pharmacol. 1997 Jun;19(5):343-50. PMID: 9379783. 12: Kuridze N, Czernicki Z, Jarus-Dziedzic K, Jurkiewicz J, Cervos-Navarro J. Regional differences of cerebrovascular reactivity effected by calcium channel blocker - dotarizine. J Neurol Sci. 2000 Apr 1;175(1):13-6. doi: 10.1016/s0022-510x(00)00275-6. PMID: 10785251. 13: Jarus-Dziedzic K, Czernicki Z, Cervos-Navarro J, Jurkiewicz J. Effect of oral administration of dotarizine on cerebrovasculature subjected to constriction followed by dilatation in rabbits. Acta Neurochir (Wien). 1999;141(11):1209-12. doi: 10.1007/s007010050420. PMID: 10592122. 14: Novalbos J, Abad-Santos F, Zapater P, Alvarez J, Alonso MT, Montero M, García AG. Novel antimigraineur dotarizine releases Ca2+ from caffeine-sensitive Ca2+ stores of chromaffin cells. Br J Pharmacol. 1999 Oct;128(3):621-6. doi: 10.1038/sj.bjp.0702853. PMID: 10516641; PMCID: PMC1571692. 15: 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 Neuropathol. 1998;36(2):101-8. PMID: 9757621. 16: Kuridze N, Czernicki Z, Jarus-Dziedzic K, Jurkiewicz J, Cervos-Navarro J. Vasostabilizing effect of Dotarizine (Ca(2+)-channel blocker) on cerebrovascular reactivity in rabbits. Neurol Res. 2000 Mar;22(2):229-32. doi: 10.1080/01616412.2000.11740664. PMID: 10763515. 17: Belcheva S, Petkov VD, Konstantinova E, Petkov VV, Boyanova E. Effects on nociception of the Ca2+ and 5-HT antagonist dotarizine and other 5-HT receptor agonists and antagonists. Acta Physiol Pharmacol Bulg. 1995;21(4):93-8. PMID: 8830881. 18: Petkov VD, Belcheva S, Konstantinova E, Petkov VV. Does nitric oxide participate in the mechanism of action of dotarizine? Acta Physiol Pharmacol Bulg. 1998;23(3-4):93-9. PMID: 10672335. 19: Petkov VD, Konstantinova E, Petkov VV, Belcheva S, Kehayov R, Vaglenova J. Memory effects of the Ca2+ and 5-HT antagonists dotarizine and flunarizine. Acta Physiol Pharmacol Bulg. 2000;25(2):43-50. PMID: 11140170. 20: Gallego-Sandín S, Novalbos J, Rosado A, Cano-Abad MF, Arias E, Abad-Santos F, García AG. Albumin prevents mitochondrial depolarization and apoptosis elicited by endoplasmic reticulum calcium depletion of neuroblastoma cells. Eur J Pharmacol. 2005 Sep 27;520(1-3):1-11. doi: 10.1016/j.ejphar.2005.06.044. PMID: 16153637.

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