Pizotifen

Names

[ Name ]:
Pizotifen

[Synonym ]:
4-(1-Methyl-4-piperidylidene)-9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophene
4-(9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophen-4-ylidene)-1-methylpiperidine
UNII:0BY8440V3N
Piperidine, 4-(9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thien-4-ylidene)-1-methyl-
Pizotyline
EINECS 239-632-9
Piperidine, 4-(9,10-dihydro-4H-benzo(4,5)cyclohepta(1,2-b)thien-4-ylidene)-1-methyl-
Pizotifen
Sandomigran
4-(4,5-dihydrobenzo[1,2]cyclohepta[3,4-b]thiophen-10-ylidene)-1-methylpiperidine
4-(9,10-Dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thien-4-ylidene)-1-methylpiperidine
MFCD00864192

Biological Activity

[Description]:

Pizotifen is a potent 5-HT2 receptor antagonist, with a high affinity for 5-HT1C binding site.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> 5-HT Receptor

Signaling Pathways >> Neuronal Signaling >> 5-HT Receptor

Research Areas >> Neurological Disease

[Target]

5-HT2A Receptor

5-HT1C Receptor

[In Vitro]

Pizotifen is a potent 5-HT2 receptor antagonist, with a high affinity for 5-HT1C binding site[1]. Pizotifen is an antidepresent 5-HT2A receptor antagonist and has the capacity to inhibit serotonin-enhanced ADP-induced platelet aggregation[2].

[In Vivo]

The weights of the fetuses are significantly reduced by all administered doses of Pipethiadene and Pizotifen; the weights of the placentas are significantly reduced after 0.6 and 1.2 mg/kg Pipethiadene and only after the middle dose of Pizotifen. The means of the implantations, live, dead fetuses, resorptions and the occurrence of external, skeletal and visceral anomalies do not differ from the control group. The number of chromosome aberrations in the bone marrow cells of treated mice does not differ significantly from the negative control group. The micronucleus test reveals no elevation in the frequency of micronuclei as compared to the control group. After the two higher doses of both Pipethiadene and Pizotifen maleate, the mitotic indices are lower than in the control group[3].

[References]

[1]. Mylecharane EJ, et al. 5-HT2 receptor antagonists and migraine therapy. J Neurol. 1991;238 Suppl 1:S45-52.

[2]. Lin OA, et al. The antidepressant 5-HT2A receptor antagonists pizotifen and cyproheptadine inhibit serotonin-enhanced platelet function. PLoS One. 2014 Jan 23;9(1):e87026.

[3]. Ujházy E, et al. Teratological and cytogenetical evaluation of two antihistamines (pipethiadene and pizotifen maleate) in mice. Agents Actions. 1988 Apr;23(3-4):376-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
436.7±45.0 °C at 760 mmHg

[ Melting Point ]:
140-142°C

[ Molecular Formula ]:
C₁₉H₂₁NS

[ Molecular Weight ]:
295.442

[ Flash Point ]:
217.9±28.7 °C

[ Exact Mass ]:
295.139465

[ PSA ]:
31.48000

[ LogP ]:
6.13

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.631

[ Storage condition ]:
Refrigerator

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TM7165000

CHEMICAL NAME :: Piperidine, 4-(9,10-dihydro-4H-benzo(4,5)cyclohepta(1,2-b)thien-4 -ylidene)-1-methyl-

CAS REGISTRY NUMBER :: 15574-96-6

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C19-H21-N-S

MOLECULAR WEIGHT :: 295.47

WISWESSER LINE NOTATION :: T C576 BY FS&T&J BU- DT6N DYTJ A1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 12857 ug/kg/12D-I

TOXIC EFFECTS :: Liver - jaundice, other or unclassified

REFERENCE :: AIMDAP Archives of Internal Medicine. (AMA, 535 N. Dearborn St., Chicago, IL 60610) V.1- 1908- Volume(issue)/page/year: 144,815,1984

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 410 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PHMCAA Pharmacologist. (American Soc. for Pharmacology and Experimental Therapeutics, 9650 Rockville Pike, Bethesda, MD 20014) V.1- 1959- Volume(issue)/page/year: 12,297,1970

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H361

[ Precautionary Statements ]:
P281

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
26-37/39

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
TM7165000

Articles

Method development for impurity profiling in SFC: The selection of a dissimilar set of stationary phases.

J. Pharm. Biomed. Anal. 111 , 333-43, (2015)

Supercritical fluid chromatography (SFC) is drawing considerable interest as separation technique in the pharmaceutical industry. The technique is already well established in chiral separations both a...

Efficacy of amitriptyline, pizotifen and propranolol in the prevention of migraine.

Mymensingh Med. J. 22(1) , 93-100, (2013)

This intervention study conducted in the Neurology outpatient Department of Mymensingh Medical College Hospital (MMCH) from January 2006 to December 2007 to compare efficacy of amitriptyline, pizotife...

Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat.

Eur. J. Pharmacol. 535(1-3) , 234-42, (2006)

This study set out to analyse the potential ability of some 5-hydroxytryptamine (5-HT) receptor ligands widely used in cardiovascular experimental models to interact with vascular alpha1-adrenoceptors...