Details
Stereochemistry | ACHIRAL |
Molecular Formula | C26H28N2.ClH |
Molecular Weight | 404.975 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.C(\C=C\C1=CC=CC=C1)N2CCN(CC2)C(C3=CC=CC=C3)C4=CC=CC=C4
InChI
InChIKey=LYXJDKBTSDYXQV-RSGUCCNWSA-N
InChI=1S/C26H28N2.ClH/c1-4-11-23(12-5-1)13-10-18-27-19-21-28(22-20-27)26(24-14-6-2-7-15-24)25-16-8-3-9-17-25;/h1-17,26H,18-22H2;1H/b13-10+;
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/26051684Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/2015612
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26051684
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/2015612
Cinnarizine is a piperazine derivative with antihistaminic, antiserotonergic, antidopaminergic, and calcium channel-blocking activities. It inhibits calcium translocation across the vestibular sensory cells in the ampullae and maintains endolymph flow by preventing constriction of the stria vascularis. It is currently used for the treatment of nausea, vomiting, and vertigo caused by Meniere’s disease and other vestibular disorders. Cinnarizine is also used for prevention and treatment of motion sickness. Chronic use of cinnarizine may induce extrapyramidal symptoms.
CNS Activity
Originator
Sources: https://www.google.com/patents/US2882271
Curator's Comment: reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/26051684 # Janssen Pharmaceutical
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL217 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7714010 |
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Target ID: CHEMBL2363032 |
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Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | STUGERON Approved UseCinnarizine helps symptoms caused by balance or movement problems. Cinnarizine tablets are used to control travel sickness, and for problems with balance (such as Ménières disease) to treat symptoms of feeling dizzy or lightheaded, ringing in the ears, feeling sick (nausea) and being sick (vomiting). |
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Preventing | STUGERON Approved UseCinnarizine helps symptoms caused by balance or movement problems. Cinnarizine tablets are used to control travel sickness, and for problems with balance (such as Ménières disease) to treat symptoms of feeling dizzy or lightheaded, ringing in the ears, feeling sick (nausea) and being sick (vomiting). |
PubMed
Title | Date | PubMed |
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Anticonvulsive properties of cinnarizine and flunarizine in rats and mice. | 1975 Sep |
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Extrapyramidal and depressive side reactions with flunarizine and cinarizine. | 1989 Feb |
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Cholestasis associated with cinnarizine. | 1990 Dec 1 |
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Calcium-entry blockers-induced parkinsonism: possible role of inherited susceptibility. | 1992 Spring |
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[Drug-induced parkinsonism. Clinical aspects compared with Parkinson disease]. | 1998 Jul |
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Etiology of parkinsonism in a Brazilian movement disorders clinic. | 1998 Jun |
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Cinnarizine-induced parkinsonism: ten years later. | 1998 May |
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Cinnarizine-induced cholestasis. | 1999 Mar |
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[Akathisia, parkinsonism and depression induced by cinnarizine: a case report]. | 1999 May 1-15 |
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Quantitative prediction of catalepsy induced by amoxapine, cinnarizine and cyclophosphamide in mice. | 2000 May |
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Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development. | 2010 Dec |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.medicines.org.uk/emc/PIL.4027.latest.pdf
Stugeron® 15 mg tablets
Cinnarizine
For travel sickness
Adults and children over 12 years old:
• 2 tablets 2 hours before travelling then
• 1 tablet every 8 hours during the journey
Children aged 5 – 12 years old:
• 1 tablet 2 hours before travelling then
• ½ a tablet every 8 hours during the journey
For problems with balance
Adults and children over 12 years old:
• 2 tablets 3 times a day
Children aged 5-12 years old:
• 1 tablet 3 times a day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2582001
10 uM cinnarizine prevented histamine-induced rat mesangial cell and glomerular contraction.
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD