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Pizotifen

Antihistamine Physicochemical properties Instruction Precaution Adverse reaction
Pizotifen
Pizotifen structure
CAS No.
15574-96-6
Chemical Name:
Pizotifen
Synonyms
Litec;bc105;BC 105;PIZOTIFEN;Pizotifan;Pizotylene;Pizotyline;Pizotifenum;Sandomigram;Sandomigran
CBNumber:
CB4230373
Molecular Formula:
C19H21NS
Formula Weight:
295.44
MOL File:
15574-96-6.mol

Pizotifen Properties

Melting point:
140-142°C
Boiling point:
436.7±45.0 °C(Predicted)
Density 
1.164±0.06 g/cm3(Predicted)
storage temp. 
room temp
solubility 
DMSO: ≥8mg/mL
pka
pKa 6.95 (Uncertain)
form 
powder
Merck 
14,7515
CAS DataBase Reference
15574-96-6(CAS DataBase Reference)
NIST Chemistry Reference
Pizotyline(15574-96-6)
ATC code
N02CX01
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07,GHS08
Signal word  Warning
Hazard statements  H302-H361
Precautionary statements  P281
Hazard Codes  Xi,Xn
Risk Statements  36/37/38-22-63
Safety Statements  26-37/39-36/37
WGK Germany  3
RTECS  TM7165000

Pizotifen price More Price(4)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich B9688 Pizotifen ≥98% (HPLC) 15574-96-6 10mg $82.6 2021-03-22 Buy
Sigma-Aldrich B9688 Pizotifen ≥98% (HPLC) 15574-96-6 50mg $326 2021-03-22 Buy
TCI Chemical P2344 Pizotifen >98.0%(HPLC) 15574-96-6 50mg $42 2021-03-22 Buy
TCI Chemical P2344 Pizotifen >98.0%(HPLC) 15574-96-6 200mg $118 2021-03-22 Buy

Pizotifen Chemical Properties,Uses,Production

Antihistamine

Pizotyline is also referred to as pizotifene and pizotifen malate. It is a chemical synthetic antihistamine. Its chemical structure is similar to that of heptaidime and amitriptyline. It has a strong anti 5serotonin and antihistamine effect and weak anti acetylcholine action, which is one of the commonly used drugs to prevent migraine. This product also inhibits the analgesic effect of bradykinin (BK) on the peripheral nerve and its sedative and antidepressant effects. This product can reduce the tolerance to ethanol, and can strengthen the effect of diazepam, sedative and tricyclic antidepressant. It is clinically used in typical and atypical migraine. It can reduce symptoms, reduce the number of episodes and duration, and the effect is significant. But it has no immediate effect on the acute attack of migraine. It can be used in erythromelalgia, angioedema, chronic urticaria, skin scratch disease etc.. It has also been reported that pizotyline can be used for the treatment of the carcinoid syndrome caused diarrhea, facial flushing and carotid artery pain as well as polycythemia induced pruritus.

Physicochemical properties

It is white needle like crystal, odorless, with bitter taste. The melting point is 147.5 151.5 centigrade. It can dissolve in organic solvent or acid solution, such as ethanol, chloroform, etc., insoluble in water. Pizotyline is synthesized by the multistep reaction using 2chloromethyl thiophene as raw material. It's an analgesic and mainly used for the treatment of typical and atypical migraine. It can also be used for chronic urticaria, atrial and ventricular premature beat.

Instruction

Precaution

Adverse reaction

Chemical Properties

White to Off-White Solid

Originator

Sandomigran ,Sandoz ,Italy ,1972

Uses

benzocycloheptane based drug

Uses

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

Definition

ChEBI: A benzocycloheptathiophene that is 9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophene 4-ylidene)-1-methylpiperidine which is joined from the 4 position to the 4 position of an N-methylpiperidine moiety b a double bond. It is a sedating antihistamine, with strong serotonin antagonist and weak antimuscarinic activity. It is generally used as the malate salt for the treatment of migraine and the prevention of headache attacks during cluster periods.

Indications

Pizotifen, a potent antihistamine and antiserotonin agent usually prescribed for migraine prophylaxis, has had reported success in patients with polycythemia vera.

Manufacturing Process

(A) Preparation of Thenylidene-(2)-Phthalide: 24.2 g of thienyl-(2)-acetic acid, 52.0 g of phthalic acid anhydride, 4.0 g of anhydrous sodium acetate and 125 ml of 1-methylpyrrolidone-(2) are heated while stirring in an open flask for 3 hours to 205° to 208°C, while nitrogen is passed through. It is then cooled and the viscous reaction mixture poured into 1 liter of water. The precipitated substance is filtered off, washed with water and then dissolved in 200 ml of chloroform. After filtering off some undissolved substance, shaking is effected twice with 100 ml of 2 N sodium carbonate solution and then with water, drying is then carried out over sodium sulfate and the volume is reduced by evaporation. The crude phthalide is repeatedly recrystallized from ethanol, while treating with animal charcoal. It melts at 114° to 115°C.
(B) Preparation of o-[2-Thienyl-(2')-Ethyl]Benzoic Acid: 24.0 g of thenylidene(2)-phthalide, 8.8 g of red pulverized phosphorus, 240 ml of hydrochloric acid (d = 1.7) and 240 ml of glacial acetic acid are heated to boiling under nitrogen and while stirring vigorously. 70 ml toluene are then added and 6.0 g of red phosphorus added in small portions over a period of 1 hour. It is then poured into 3 liters of ice water, stirred with 300 ml of chloroform and the phosphorus removed by filtration.
The chloroform phase is then removed, the aqueous phase extracted twice more with 200 ml of chloroform and the united extracts shaken out 4 times,each time with 200 ml of 2 N sodium hydroxide solution. The alkaline solution is then rendered acid to Congo red reagent, using hydrochloric acid and extracted 3 times with chloroform. After drying over sodium sulfate and evaporating the solvent, the residue is chromatographed on aluminum oxide (Activity Stage V). The substance eluted with benzene and benzene/chloroform (1:1) is recrystallized from chloroform/hexane (1:1); MP 107° to 109°C.
(C) Preparation of 9,10-Dihydro-4H-Benzo[4,5]Cyclohepta[1,2-b]Thiophen(4)-One: 200 ml of 85% phosphoric acid and 112 g of phosphorus pentoxide are heated to 135°C. 7.0 g of o-[2-thienyl-(2')-ethyl]benzoic acid are then introduced while stirring thoroughly over a period of 30 min. Stirring is then continued for another hour at 135°C and the reaction mixture is then stirred into 1 liter of ice water. Extraction is then effected 3 times, using 250 ml ether portions, the ethereal extract is washed with 2 N sodium carbonate solution, dried over sodium sulfate and reduced in volume by evaporation. The residue is boiled up with 55 ml of ethanol, the solution freed of resin by decanting and then stirred at room temperature for 6 hours with animal charcoal. It is then filtered off, reduced in volume in a vacuum and the residue distilled. BP 120° to 124°C/0.005 mm, nD24.5 = 1.6559.
(D) Preparation of 4-[1'-Methyl-Piperidyl-(4')]-9,10-Dihydro-4HBenzo[4,5]Cyclohepta[1,2b]Thiophen-(4)-ol: 0.94 g of magnesium filings which have been activated with iodine are covered with a layer of absolute tetrahydrofuran and etched with a few drops of ethylene bromide. A solution of 5.0 g of 1-methyl-4-chloropiperidine in 5 ml of tetrahydrofuran is then added dropwise and boiling then effected for a further hour under reflux. After cooling to room temperature, the solution of 4.5 g of 9,10-dihydro-4Hbenzo[4,5]cyclohepta[1,2-b]thiophen-(4)-one in 5 ml of tetrahydrofuran is added dropwise.
Stirring is carried out first for 3 hours at room temperature and then for 2 hours at boiling temperature, it is then cooled and poured into 300 ml of icecold 20% ammonium chloride solution. It is then shaken out with methylene chloride, the methylene chloride solution washed with water and shaken 3 times with 30 ml portions of aqueous 2 N tartaric acid solution. The tartaric acid extract is rendered alkaline while cooling thoroughly and then extracted twice with methylene chloride. After washing with water, drying over potassium carbonate and reducing in volume by evaporation, the residue is recrystallized from ethanol. MP 197° to 199°C.
(E) Preparation of 4-[1'-Methyl-Piperidylidene-(4')]-9,10-Dihydro-4HBenzo[4,5]Cyclohepta[1,2-b]Thiophene Hydrochloride: 2 g of 4-[1'-methylpiperidyl-(4')]-9,10-dihydro4H-benzo[4,5]cyclohepta[1,2-b]thiophen-(4)-ol, 60 ml of glacial acetic acid and 20 ml of concentrated hydrochloric acid are boiled for 30 minutes under reflux. After evaporating in a vacuum, the residue is triturated with 3 ml of acetone, the precipitated hydrochloride is then filtered off and it is recrystallized from isopropanol/ether. MP 261° to 263°C (decomposition).

brand name

Sandomigran (Novartis).

Therapeutic Function

Migraine therapy

Pizotifen Preparation Products And Raw materials

Raw materials

Preparation Products


Pizotifen Suppliers

Global( 165)Suppliers
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QINGDAO HONG JIN CHEMCIAL CO.,LTD.
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Hebei Guanlang Biotechnology Co., Ltd.
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BOC Sciences
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Shaanxi Dideu Medichem Co. Ltd
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WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
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View Lastest Price from Pizotifen manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-12-06 Pizotifen
15574-96-6
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-11-30 Pizotifen
15574-96-6
US $4603.00 / g 100g 99% 100kg Baoji Guokang Bio-Technology Co., Ltd.
2021-07-20 Pizotifen
15574-96-6
US $1.00-1.00 / Kg/Drum 1g 99% 50tons Shaanxi Dideu Medichem Co. Ltd

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