Cyclizine

Title: Cyclizine
CAS Registry Number: 82-92-8
CAS Name: 1-Diphenylmethyl-4-methylpiperazine
Additional Names: N-benzhydryl-N¢-methylpiperazine; N-methyl-N¢-benzhydrylpiperazine; (N-benzhydryl)(N¢-methyl)diethylenediamine
Manufacturers' Codes: Compd 47-83; Wellcome prepn 47-83
Trademarks: Marzine (GlaxoWellcome); Marezine (Himmel)
Molecular Formula: C18H22N2
Molecular Weight: 266.38
Percent Composition: C 81.16%, H 8.32%, N 10.52%
Literature References: Prepn: R. Baltzly et al., J. Org. Chem. 14, 775 (1949); eidem, US 2630435 (1953 to Burroughs Wellcome). Metabolism: R. Kuntzman et al., Ann. N.Y. Acad. Sci. 226, 131 (1973). Physical properties and analysis: S. A. Benezra, Anal. Profiles Drug Subs. 6, 83 (1977). Crystallographic study: V. Bertolasi et al., Acta Crystallogr. B36, 1975 (1980). HPLC determn: R. B. Walker, I. Kanfer, J. Chromatogr. B 672, 172 (1995). Clinical antiemetic efficacy: G. Rowlands, W. J. Currie, Br. J. Clin. Pract. 30, 197 (1976); W. N. Chestnutt et al., Eur. J. Anaesthesiol. 3, 27 (1986).
Properties: Light-sensitive crystals from petr ether, mp 105.5-107.5°. uv max (0.1N HCl): 269, 263, 258, 225 (e 540, 742, 694, 11300). Soly in g/ml at 25°: chloroform 1.1; ether 0.17; ethanol 0.17; in mg/ml: water <0.1.
Melting point: mp 105.5-107.5°
Absorption maximum: uv max (0.1N HCl): 269, 263, 258, 225 (e 540, 742, 694, 11300)
Derivative Type: Hydrochloride
CAS Registry Number: 303-25-3
Trademarks: Valoid (Glaxo Wellcome)
Molecular Formula: C18H22N2.HCl
Molecular Weight: 302.84
Percent Composition: C 71.39%, H 7.66%, N 9.25%, Cl 11.71%
Properties: Crystals, moderately sol in water. Protect from light.
Therap-Cat: Antiemetic.
Therap-Cat-Vet: Antiemetic.
Keywords: Antiemetic.
Cyclobarbital Cyclobendazole Cyclobenzaprine Cyclobutane Cyclobutyrol

Cyclizine
Cyclizine BLUE Structural Formula.svg
Cyclizine 3d balls.png
Systematic (IUPAC) name
1-benzhydryl-4-methyl-piperazine
Clinical data
Trade names Marezine, Valoid, Nausicalm
AHFS/Drugs.com Consumer Drug Information
Pregnancy cat. A (AU)
Legal status Pharmacist Only (S3) (AU) POM (UK) OTC (Netherlands)
Routes Oral, IM, IV
Pharmacokinetic data
Metabolism N-demethylated to inactive norcyclizine[citation needed]
Half-life 20 hours
Identifiers
CAS number 82-92-8 YesY
ATC code R06AE03
PubChem CID 6726
DrugBank DB01176
ChemSpider 6470 YesY
UNII QRW9FCR9P2 YesY
KEGG D03621 YesY
ChEBI CHEBI:3994 YesY
ChEMBL CHEMBL648 YesY
Chemical data
Formula C18H22N2 
Mol. mass 266.381 g/mol
 YesY (what is this?)  (verify)

Cyclizine is an antihistamine drug used to treat nausea, vomiting and dizziness associated with motion sickness, vertigo and post-operatively following administration of general anaesthesia and opioids.