Cinnarizine

Cinnarizine
Clinical data
Trade names	Stugeron, Stunarone, Cinarin
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	N07CA02 (WHO) ;
Legal status
Legal status	UK: P (Pharmacy medicines);
Pharmacokinetic data
Bioavailability	Low
Metabolism	Entire
Elimination half-life	3–4 hours
Excretion	1⁄3 urine, 2⁄3 faeces
Identifiers
	IUPAC name (E)-1-(Diphenylmethyl)-4-(3-phenylprop-2-enyl)piperazine;
CAS Number	298-57-7 ;
PubChem CID	1547484;
DrugBank	DB00568 ;
ChemSpider	1264793 ;
UNII	3DI2E1X18L;
KEGG	D01295 ;
ChEBI	CHEBI:31403 ;
ChEMBL	ChEMBL43064 ;
CompTox Dashboard (EPA)	DTXSID3022821 DTXSID80859311, DTXSID3022821 ;
ECHA InfoCard	100.005.514
Chemical and physical data
Formula	C26H28N2
Molar mass	368.524 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c1c(cccc1)C(c2ccccc2)N3CCN(CC3)C\C=C\c4ccccc4;
	InChI InChI=1S/C26H28N2/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/b13-10+ ; Key:DERZBLKQOCDDDZ-JLHYYAGUSA-N ;
	(verify)

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.