1-[(4-chlorophenyl)(phenyl)methyl]-4-[(3-methylphenyl)methyl]piperazine

• ChemBase ID: 617
• Molecular Formular: C25H27ClN2
• Molecular Mass: 390.94828
• Monoisotopic Mass: 390.18627655
• SMILES: Clc1ccc(C(N2CCN(CC2)Cc2cc(ccc2)C)c2ccccc2)cc1
• Canonical SMILES: Clc1ccc(cc1)C(c1ccccc1)N1CCN(CC1)Cc1cccc(c1)C
• InChI: InChI=1S/C25H27ClN2/c1-20-6-5-7-21(18-20)19-27-14-16-28(17-15-27)25(22-8-3-2-4-9-22)23-10-12-24(26)13-11-23/h2-13,18,25H,14-17,19H2,1H3
• InChIKey: OCJYIGYOJCODJL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(4-chlorophenyl)(phenyl)methyl]-4-[(3-methylphenyl)methyl]piperazine
• IUPAC Traditional name: (+-)-meclizine; meclizine
• Brand Name: Ancolan; Ancolon; Antivert; Antivert/25; Antivert/50; Bonadettes; Bonadoxin; Bonamine; Bonine; Calmonal; Chiclida; Diadril; Dramamine; Dramamine II; Histamethine; Histamethizine; Histametizine; Histametizyne; Itinerol; Marex; Meclicot; Meclizine Hcl; Meclozine; Medivert; Monamine; Navicalm; Neo-Istafene; Neo-Suprimal; Neo-Suprimel; Parachloramine; Peremesin; Postafene; Ravelon; Sabari; Sea-Legs; Siguran; Subari; Suprimal; Travelon; Veritab; Vomisseis; Vomissels
• Synonyms: Meclizine; 1-[(4-chlorophenyl)(phenyl)methyl]-4-[(3-methylphenyl)methyl]piperazine; Meclozine

Database IDs

• CAS Number: 569-65-3
• MDL Number: MFCD00242697
• PubChem SID: 160964080; 46507782
• PubChem CID: 4034
• ATC CODE: R06AE05
• CHEMBL: 1623
• Chemspider ID: 3894
• DrugBank ID: DB00737
• IUPHAR ligand ID: 2757
• Unique Ingredient Identifier: 3L5TQ84570
• Wikipedia Title: Meclozine
• Medline Plus: a682548

CALCULATED PROPERTIES

JChem

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.7845445
• LogD (pH = 7.4): 5.558482
• Log P: 6.3879414
• Molar Refractivity: 119.3922 cm^3
• Polarizability: 46.576492 Å^3
• Polar Surface Area: 6.48 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.59
• LOG S: -5.58
• Solubility (Water): 1.03e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.1gm/100ml
• Boiling Point: 230°C (446°F)
• Hydrophobicity(logP): 5.8; 6.732

Pharmacology Properties

• Admin Routes: Oral, Sublingual/Buccal
• Half Life: 6 hours
• Metabolism: hepatic
• Legal Status: OTC (US); OTC (Canada)
• Pregnancy Category: B (US)

Product Information

• Purity: 95%

DETAILS

DrugBank - DB00737

• Drug Groups: approved
• Description: A histamine H1 antagonist used in the treatment of motion sickness, vertigo, and nausea during pregnancy and radiation sickness. [PubChem]
• Indication: For the prevention and treatment of nausea, vomiting, or dizziness associated with motion sickness.
• Pharmacology: Meclizine, a piperazine-derivative H₁-receptor antagonist similar to buclizine, cyclizine, and hydroxyzine, is used as an antivertigo/antiemetic agent. Meclizine is used in the management of nausea, vomiting, and dizziness associated with motion sickness and vertigo in diseases affecting the vestibular apparatus.
• Toxicity: Symptoms of overdose include drowsiness and anticholinergic effects. LD₅₀=mg/kg (orally in rat).
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Well absorbed
• Half Life: 6 hours
• External Links: Wikipedia; RxList; Drugs.com