1-methyl-4-{6-thiatricyclo[8.4.0.03,7]tetradeca-1(14),3(7),4,10,12-pentaen-2-ylidene}piperidine

• ChemBase ID: 130384
• Molecular Formular: C19H21NS
• Molecular Mass: 295.44174
• Monoisotopic Mass: 295.13947068
• SMILES: s1c2c(cc1)C(=C1CCN(C)CC1)c1c(cccc1)CC2
• Canonical SMILES: CN1CCC(=C2c3ccsc3CCc3c2cccc3)CC1
• InChI: InChI=1S/C19H21NS/c1-20-11-8-15(9-12-20)19-16-5-3-2-4-14(16)6-7-18-17(19)10-13-21-18/h2-5,10,13H,6-9,11-12H2,1H3
• InChIKey: FIADGNVRKBPQEU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-methyl-4-{6-thiatricyclo[8.4.0.0^3,^7]tetradeca-1(14),3(7),4,10,12-pentaen-2-ylidene}piperidine; 1-methyl-4-{6-thiatricyclo[8.4.0.0^3,^7]tetradeca-1(10),3(7),4,11,13-pentaen-2-ylidene}piperidine
• IUPAC Traditional name: litec
• Synonyms: Pizotifen; Pizotyline; 4-(9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thien-4-ylidene)-1-methylpiperidine; Pizotifen; Pizotifen; 4-(9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thien-4-ylidene)-1-methylpiperidine; 4-(1-Methyl-4-piperidylidene)-9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophene; BC 105; Litec; Polomigran; Sandomigran; Pizotyline

Database IDs

• CAS Number: 15574-96-6
• EC Number: 239-632-9
• MDL Number: MFCD00864192
• PubChem SID: 162224663
• PubChem CID: 27400
• ATC CODE: N02CX01
• CHEMBL: 294951
• Chemspider ID: 25497
• IUPHAR ligand ID: 93
• KEGG ID: D05523
• Unique Ingredient Identifier: 0BY8440V3N
• Wikipedia Title: Pizotifen

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.054434
• LogD (pH = 7.4): 3.8149393
• Log P: 4.4922447
• Molar Refractivity: 101.1015 cm^3
• Polarizability: 34.915295 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: ≥8 mg/mL; Methanol
• Apperance: powder; White to Off-White Solid
• Melting Point: 140-142°C

Safety Information

• Storage Condition: Refrigerator
• RTECS: TM7165000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-22
• Safety Statements: 36/37
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H361
• GHS Precautionary statements: P281
• Storage Temperature: room temp

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 78%
• Excretion: 18% feces, 55% urine (both as metabolites).
• Half Life: 23h
• Metabolism: Glucuronidation (main route). N-glucuronide accounts for >50% of plasma and 60–70% of urinary excreted drug
• Protein Bound: 91%
• Pregnancy Category: B1 (Australia)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H21NS

DETAILS

Sigma Aldrich - B9688

Biochem/physiol Actions
Pizotifen is a serotonin antagonist acting mainly at the 5-HT1, 5-HT2A and 5HT2C receptors with some antihistamine activity. It is used for the prevention of vascular headache including migraine and cluster headache.

Toronto Research Chemicals - P552800

Serotonin antagonist structurally related to Cyproheptadine. Antimigraine; appetite stimulant.

REFERENCES

• Geraud, G., et al.: Clin. Ther., 26, 1305 (2004)
• Bolay, H., et al.: Nat. Med., 8, 136 (2004)
• Scher, A., et al.: Pain, 106, 81 (2004)
• Richter, F., et al.: J. Cereb. Blood Flow Metab., 25, 1225 (2004)