Cinnarizine

Cinnarizine
Clinical data
Trade namesStugeron, Stunarone, Cinarin
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityLow[1]
MetabolismEntire[3][4]
Elimination half-life3–4 hours[2]
Excretion1⁄3 urine, 2⁄3 faeces[3]
Identifiers
  • (E)-1-(Diphenylmethyl)-4-(3-phenylprop-2-enyl)piperazine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.514 Edit this at Wikidata
Chemical and physical data
FormulaC26H28N2
Molar mass368.524 g·mol−1
3D model (JSmol)
  • c1c(cccc1)C(c2ccccc2)N3CCN(CC3)C\C=C\c4ccccc4
  • 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+ checkY
  • Key:DERZBLKQOCDDDZ-JLHYYAGUSA-N checkY
  (verify)

Cinnarizine is an antihistamine and calcium channel blocker of the diphenylmethylpiperazine group.[5] It is prescribed for nausea and vomiting due to motion sickness[6] or other sources such as chemotherapy,[7] vertigo,[8] or Ménière's disease.[9] Cinnarizine is one of the leading causes of drug-induced parkinsonism.[5]

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".[10] 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.[11]

  1. ^ Cite error: The named reference Kalava was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference Castaneda was invoked but never defined (see the help page).
  3. ^ a b Cite error: The named reference Deka was invoked but never defined (see the help page).
  4. ^ Cite error: The named reference Kariya was invoked but never defined (see the help page).
  5. ^ a b Terland O, Flatmark T (June 1999). "Drug-induced parkinsonism: cinnarizine and flunarizine are potent uncouplers of the vacuolar H+-ATPase in catecholamine storage vesicles". Neuropharmacology. 38 (6): 879–82. doi:10.1016/s0028-3908(98)00233-0. PMID 10465691. S2CID 40061724.
  6. ^ Nicholson AN, Stone BM, Turner C, Mills SL (June 2002). "Central effects of cinnarizine: restricted use in aircrew". Aviation, Space, and Environmental Medicine. 73 (6): 570–4. PMID 12056673.
  7. ^ Wilder-Smith CH, Schimke J, Osterwalder B, Senn HJ (1991). "Cinnarizine for prevention of nausea and vomiting during platin chemotherapy". Acta Oncologica. 30 (6): 731–4. doi:10.3109/02841869109092448. PMID 1958394.
  8. ^ Pianese CP, Hidalgo LO, González RH, Madrid CE, Ponce JE, Ramírez AM, Morán LM, Arenas JE, Rubio AT, Uribe JO, Abiuso J, Hanuch E, Alegría J, Volpi C, Flaskamp R, Sanjuán AP, Gómez JM, Hernández J, Pedraza A, Quijano D, Martínez C, Castañeda JR, Guerra OJ, F GV (May 2002). "New approaches to the management of peripheral vertigo: efficacy and safety of two calcium antagonists in a 12-week, multinational, double-blind study". Otology & Neurotology. 23 (3): 357–63. doi:10.1097/00129492-200205000-00023. PMID 11981396. S2CID 23282116.
  9. ^ Arab SF, Düwel P, Jüngling E, Westhofen M, Lückhoff A (June 2004). "Inhibition of voltage-gated calcium currents in type II vestibular hair cells by cinnarizine". Naunyn-Schmiedeberg's Archives of Pharmacology. 369 (6): 570–5. doi:10.1007/s00210-004-0936-3. PMID 15138660. S2CID 27410833.
  10. ^ "The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances 2011" (PDF). WHO. Retrieved 2015-03-12.
  11. ^ Lucertini M, Mirante N, Casagrande M, Trivelloni P, Lugli V (May 2007). "The effect of cinnarizine and cocculus indicus on simulator sickness". Physiology & Behavior. 91 (1): 180–90. doi:10.1016/j.physbeh.2007.02.008. PMID 17434541. S2CID 45239084.