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Substance Name: Cinnarizine [USAN:INN:BAN:JAN]
RN: 298-57-7
UNII: 3DI2E1X18L
InChIKey: DERZBLKQOCDDDZ-JLHYYAGUSA-N

Note

  • A piperazine derivative having histamine H1-receptor and calcium-channel blocking activity with vasodilating and antiemetic properties but it induces PARKINSONIAN DISORDERS.

Molecular Formula

  • C26-H28-N2

Molecular Weight

  • 368.5212
 

Classification Codes

  • Antihistaminic
  • Calcium Channel Blockers
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Histamine Agents
  • Histamine Antagonists
  • Histamine H1 Antagonists
  • Human Data
  • Membrane Transport Modulators
  • Neurotransmitter Agents
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Cinnarizine
  • Cinnarizine [USAN:INN:BAN:JAN]

MeSH Heading

  • Cinnarizine

Synonyms

  • 1-(Diphenylmethyl)-4-(3-phenyl-2-propenyl)piperazine
  • 1-Benzhydryl-4-cinnamylpiperazin
  • 1-Cinnamyl-4-(diphenylmethyl)piperazine
  • 5-23-01-00233 (Beilstein Handbook Reference)
  • 516 MD
  • Aplactan
  • BRN 0626121
  • Cerepar
  • Cero-Aterin
  • Cinarizina
  • Cinarizina [INN-Spanish]
  • Cinazyn
  • Cinnageron
  • Cinnarizin
  • Cinnarizine
  • Cinnarizinum
  • Cinnarizinum [INN-Latin]
  • Dimitron
  • Dimitronal
  • EINECS 206-064-8
  • Folcodal
  • Glanil
  • Labyrin
  • Lazeta
  • Libotasin
  • Marisan
  • MD 516
  • Midronal
  • Mitronal
  • R 1575
  • R 516
  • Ranitin
  • Senoger
  • Sepan
  • Stonoron
  • Stugeron
  • Stutgeron
  • Stutgin
  • Toliman
  • UNII-3DI2E1X18L
  • Votegol
  • Zepamol

Systematic Names

  • Cinnarizine
  • Piperazine, 1-(diphenylmethyl)-4-(3-phenyl-2-propenyl)-
  • Piperazine, 1-cinnamyl-4-(diphenylmethyl)-

Registry Numbers

CAS Registry Number

  • 298-57-7

FDA UNII

  • 3DI2E1X18L

Related Registry Number

  • 7002-58-6 (di-hydrochloride)

System Generated Number

  • 0000298577

Structure Descriptors

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+

InChIKey

DERZBLKQOCDDDZ-JLHYYAGUSA-N

Smiles

c1ccc(cc1)/C=C/CN2CCN(CC2)C(c3ccccc3)c4ccccc4

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 intraperitoneal > 500mg/kg (500mg/kg)   Drugs in Japan Vol. -, Pg. 515, 1990.
dog LD50 oral > 500mg/kg (500mg/kg)   Drugs in Japan Vol. -, Pg. 515, 1990.
dog LD50 subcutaneous > 500mg/kg (500mg/kg)   Drugs in Japan Vol. -, Pg. 515, 1990.
mouse LD50 intraperitoneal 730mg/kg (730mg/kg)   Medicamentos de Actualidad. Vol. 21, Pg. 443, 1985.
mouse LD50 intravenous 22mg/kg (22mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 1735, 1982.
mouse LD50 oral > 4500mg/kg (4500mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 1735, 1982.
mouse LD50 subcutaneous > 2gm/kg (2000mg/kg)   Drugs in Japan Vol. -, Pg. 515, 1990.
rat LD50 intraperitoneal 1050mg/kg (1050mg/kg)   Medicamentos de Actualidad. Vol. 21, Pg. 443, 1985.
rat LD50 intravenous 24mg/kg (24mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 1735, 1982.
rat LD50 oral > 6500mg/kg (6500mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Kiso to Rinsho. Clinical Report. Vol. 16, Pg. 1735, 1982.
rat LD50 subcutaneous > 2gm/kg (2000mg/kg)   Drugs in Japan Vol. -, Pg. 515, 1990.
women TDLo oral 252mg/kg/12W- (252mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" British Journal of Dermatology. Vol. 112, Pg. 607, 1985.
women TDLo oral 22500mg/kg/22 (22500mg/kg)   Annals of Pharmacotherpy. Vol. 26, Pg. 928, 1992.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 5.77 (none)   EXP
Water Solubility 750 mg/L 25 EXP
Vapor Pressure 1.32E-09 mm Hg 25 EST
Henry's Law Constant 4.06E-12 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.69E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.