Structure via PubChem · Public domain (PubChem)
cinnarizine
Sign in to saveAlso known as R-1575, Stugeron®, 1-Cinnamyl-4-(diphenylmethyl)piperazine, 1-Benzhydryl-4-cinnamylpiperazin, 1-(Diphenylmethyl)-4-(3-phenyl-2-propenyl)piperazine, Cinarizina, Cinnarizinum
Cinnarizine is an antihistamine and calcium channel blocker of the diphenylmethylpiperazine group. It is prescribed for nausea and vomiting due to motion sickness or other sources such as chemotherapy, vertigo, or Ménière's disease. Cinnarizine is one of the leading causes of drug-induced parkinsonism.
Chemical data
- Formula
- C26H28N2
- Molecular weight
- 368.5 g/mol
- IUPAC name
- 1-benzhydryl-4-[(E)-3-phenylprop-2-enyl]piperazine
- SMILES
- C1CN(CCN1C/C=C/C2=CC=CC=C2)C(C3=CC=CC=C3)C4=CC=CC=C4
- InChIKey
- DERZBLKQOCDDDZ-JLHYYAGUSA-N
- XLogP
- 5.8
- Polar surface area
- 6.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
1,228 papers- Cinnarizine: Comprehensive Profile.Profiles of drug substances, excipients, and related methodology · 2015
- Cinnarizine--a labyrinthine sedative.The Journal of laryngology and otology · 1980
- Cinnarizine as an alternative recommendation for migraine prophylaxis: a narrative review.Expert review of neurotherapeutics · 2020
- Application of cinnarizine in migraine prevention: A systematic review and meta-analysis.Pain practice : the official journal of World Institute of Pain · 2022
- Cinnarizine dissolving microneedles against microwave-induced brain injury.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2022
via PubMed
Wikidata facts
- Subclass of
- heterocyclic compound
- Has part
- carbon
- Mass
- 368.225
- Has use
- medication
Show 7 more facts
- Commons category
- Cinnarizine
- chemical formula
- C₂₆H₂₈N₂
- World Health Organisation international non-proprietary name
- cinnarizine
- defined daily dose
- 90
- subject has role
- H1 antagonist
- canonical SMILES
- C1CN(CCN1CC=CC2=CC=CC=C2)C(C3=CC=CC=C3)C4=CC=CC=C4
- isomeric SMILES
- C1CN(CCN1C/C=C/C2=CC=CC=C2)C(C3=CC=CC=C3)C4=CC=CC=C4
Sources (3)
via Wikidata · CC0
~13 min read
Encyclopedic overview
8 sectionsContents
- Medical uses
- Side effects
- Pharmacokinetics
- Pharmacodynamics
- Elimination
- See also
- References
- External links
Cinnarizine is an antihistamine and calcium channel blocker of the diphenylmethylpiperazine group. It is prescribed for nausea and vomiting due to motion sickness or other sources such as chemotherapy, vertigo, or Ménière's disease. Cinnarizine is one of the leading causes of drug-induced parkinsonism.
Cinnarizine was first synthesized as R1575 by Janssen Pharmaceutica in 1955. The nonproprietary name is derived from the cinnamyl substituent on the free nitrogen atom of the benzhydrylpiperazine core, combined with the generic ending "-rizine" for "antihistaminics/cerebral (or peripheral) vasodilators". It is not available in the United States or Canada. It has also been cited as one of the most used drugs for seasickness within the British Royal Navy.
Excerpted from Wikipedia’s “cinnarizine” article, available under the CC BY-SA 4.0 licence.