Details
Stereochemistry | ACHIRAL |
Molecular Formula | C26H26F2N2 |
Molecular Weight | 404.4948 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
FC1=CC=C(C=C1)C(N2CCN(C\C=C\C3=CC=CC=C3)CC2)C4=CC=C(F)C=C4
InChI
InChIKey=SMANXXCATUTDDT-QPJJXVBHSA-N
InChI=1S/C26H26F2N2/c27-24-12-8-22(9-13-24)26(23-10-14-25(28)15-11-23)30-19-17-29(18-20-30)16-4-7-21-5-2-1-3-6-21/h1-15,26H,16-20H2/b7-4+
Molecular Formula | C26H26F2N2 |
Molecular Weight | 404.4948 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Flunarizine is a selective calcium entry blocker with calmodulin binding properties and histamine H1 / dopamine D2 blocking activity. It is not available in the US but marketed in other countries for prophylaxis of a migraine, occlusive peripheral vascular disease, the vertigo of central and peripheral origin, motion sickness and as an adjuvant in the therapy of epilepsy. The drug is also investigated for the treatment of schizophrenia.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL6093 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6093793 |
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Target ID: CHEMBL339 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10571163 |
0.228 µM [IC50] | ||
Target ID: CHEMBL2362995 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10571163 |
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Target ID: CHEMBL2096682 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10571163 |
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Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20493137 |
86.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | SIBELIUM Approved UseIn the prophylaxis of a migraine. The limited information available for periods longer than 12 months has shown flunarizine to continue to be effective. Patients should be regularly reviewed to assess their response to treatment, and if a sustained attack-free period is established, interrupted flunarizine treatment should be considered. Launch Date1.23318724E12 |
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Primary | FLURIZIN Approved UseFlurizin is indicated for treatment of peripheral vascular disease |
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Primary | FLURIZIN Approved UseFlurizin is indicated for symptomatic treatment of vestibular vertigo (due to a diagnosed functional disorder of the vestibular system). |
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Primary | FLURIZIN Approved UseFlurizin is indicated for treatment of motion sickness. |
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Palliative | FLURIZIN Approved UseFlurizin is indicated for treatment of refractory epilepsy resistant to conventional antiepileptic therapy |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Anticonvulsive properties of cinnarizine and flunarizine in rats and mice. | 1975 Sep |
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Parkinsonism, tardive dyskinesia, akathisia, and depression induced by flunarizine. | 1986 Jun 7 |
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Flunarizine- and cinnarizine-induced extrapyramidal reactions. | 1987 May |
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Cardiovascular and renal actions of calcium channel blocker chemical subgroups: a search for renal specificity. | 1988 Jun |
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Drug-induced tremor of the tongue. | 1989 Feb |
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Extrapyramidal and depressive side reactions with flunarizine and cinarizine. | 1989 Feb |
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Effect of flunarizine on the attenuation of baroreflex by transient cerebral ischemia. | 1989 Jun 8 |
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Calcium-entry blockers-induced parkinsonism: possible role of inherited susceptibility. | 1992 Spring |
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Profile of capsaicin-induced mouse ear oedema as neurogenic inflammatory model: comparison with arachidonic acid-induced ear oedema. | 1993 Dec |
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Catalepsy induced by manidipine, a calcium channel blocker, in mice. | 1996 Apr |
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Catalepsy induced by calcium channel blockers in mice. | 1998 Mar |
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Evidence of sex related differences in the effects of calcium channel blockers on neuroleptic-induced catalepsy in mice. | 1999 Feb |
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Distinct features of seizures induced by cocaine and amphetamine analogs. | 1999 Jul 21 |
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Motor and electrographic response of refractory experimental status epilepticus in rats and effect of calcium channel blockers. | 2000 Feb |
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Parkinsonism and other movement disorders in outpatients in chronic use of cinnarizine and flunarizine. | 2004 Sep |
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Amphetamine-induced anxiety-related behavior in animal models. | 2007 Nov-Dec |
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Progressive supranuclear palsy-like syndrome induced by amiodarone and flunarizine. | 2009 Sep |
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EFNS guideline on the drug treatment of migraine--revised report of an EFNS task force. | 2009 Sep |
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A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle. | 2010 Feb 23 |
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Ameliorative effect of flunarizine in cisplatin-induced acute renal failure via mitochondrial permeability transition pore inactivation in rats. | 2011 Jan |
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FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. | 2013 Sep 5 |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6093793
To study the effect of flunarizine on the interaction between calmodulin and phosphodiesterase, proteins were isolated from bovine brain. PDE activity was measured using cAMP (1.2mM) as a substrate and in the presence of 5'-nucleotidase. The liberated Pi was measured in the supernatant by the method of Ames. The reaction was performed in the presence of CaCl2 and Calmodulin (positive control), in the presence of EGTA (negative control) and in the presence of various concentrations of flunarizine. IC50 determined for brain PDE was 21 uM.
Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 16:16:46 UTC 2023
by
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Record UNII |
R7PLA2DM0J
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C29578
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NCI_THESAURUS |
C333
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FDA ORPHAN DRUG |
528116
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WHO-ATC |
N07CA03
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FDA ORPHAN DRUG |
823521
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FDA ORPHAN DRUG |
857721
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WHO-VATC |
QN07CA03
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FDA ORPHAN DRUG |
9485
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FDA ORPHAN DRUG |
398513
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FDA ORPHAN DRUG |
665818
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257-937-5
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C83718
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CHEMBL30008
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100000080711
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DTXSID6045616
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D005444
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1200
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DB04841
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2686
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4459
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FLUNARIZINE
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52468-60-7
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Flunarizine
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941361
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SUB07707MIG
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R7PLA2DM0J
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m5445
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PRIMARY | Merck Index |
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SALT/SOLVATE -> PARENT |
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METABOLITE -> PARENT |
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ACTIVE MOIETY |