1-(diphenylmethyl)-4-methylpiperazine

• ChemBase ID: 1047
• Molecular Formular: C18H22N2
• Molecular Mass: 266.38068
• Monoisotopic Mass: 266.17829871
• SMILES: N1(CCN(CC1)C)C(c1ccccc1)c1ccccc1
• Canonical SMILES: CN1CCN(CC1)C(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C18H22N2/c1-19-12-14-20(15-13-19)18(16-8-4-2-5-9-16)17-10-6-3-7-11-17/h2-11,18H,12-15H2,1H3
• InChIKey: UVKZSORBKUEBAZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(diphenylmethyl)-4-methylpiperazine
• IUPAC Traditional name: wellcome
• Brand Name: Emoquil; Marazine; Marezine; Marezine Hydrochloride; Marzine; Nautazine; Ne-Devomit; Neo-Devomit; Reis-Fit; Valoid; Wellcome; Marezine, Valoid, Nausicalm
• Synonyms: Ciclizina [INN-Spanish]; Cyclizine Chloride; Cyclizine Hydrochloride; Cyclizinum [INN-Latin]; Cyclizine; 1-Benzhydryl-4-methylpiperazine

Database IDs

• CAS Number: 82-92-8; 303-25-3
• MDL Number: MFCD00023293
• PubChem SID: 46506232; 160964510
• PubChem CID: 6726
• CHEBI ID: 3994
• ATC CODE: R06AE03
• CHEMBL: 648
• Chemspider ID: 6470
• DrugBank ID: DB01176
• KEGG ID: D03621
• Unique Ingredient Identifier: QRW9FCR9P2
• Wikipedia Title: Cyclizine

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.65597045
• LogD (pH = 7.4): 2.405105
• Log P: 3.5460024
• Molar Refractivity: 84.9336 cm^3
• Polarizability: 33.39166 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.55
• LOG S: -3.55
• Solubility (Water): 7.52e-02 g/l

PROPERTIES

Physical Property

• Solubility: 1 mg/mL at 25 oC [MERCK INDEX (1996); less than]
• Hydrophobicity(logP): 3

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Admin Routes: Oral, IM, IV
• Half Life: 20 hours
• Metabolism: N-demethylated to inactive norcyclizine
• Legal Status: P/POM (UK) OTC (NL)
• Pregnancy Category: A (Au)

Product Information

• Purity: 95%

DETAILS

DrugBank - DB01176

• Drug Groups: approved
• Description: A histamine H1 antagonist given by mouth or parenterally for the control of postoperative and drug-induced vomiting and in motion sickness. (From Martindale, The Extra Pharmacopoeia, 30th ed, p935)
• Indication: For prevention and treatment of nausea, vomiting, and dizziness associated with motion sickness, and vertigo (dizziness caused by other medical problems).
• Pharmacology: Cyclizine is a piperazine-derivative antihistamine used as an antivertigo/antiemetic agent. Cyclizine is used in the prevention and treatment of nausea, vomiting, and dizziness associated with motion sickness. Additionally, it has been used in the management of vertigo in diseases affecting the vestibular apparatus. Although the mechanism by which cyclizine exerts its antiemetic and antivertigo effects has not been fully elucidated, its central anticholinergic properties are partially responsible. The drug depresses labyrinth excitability and vestibular stimulation, and it may affect the medullary chemoreceptor trigger zone. It also possesses anticholinergic, antihistaminic, central nervous system depressant, and local anesthetic effects.
• Affected Organisms: Humans and other mammals
• Biotransformation: Cyclizine is metabolised to its N-demethylated derivative, norcyclizine, which has little antihistaminic (H1) activity compared to Cyclizine.
• Half Life: 20 hours
• External Links: Wikipedia; Drugs.com