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Ziprasidone hydrochloride monohydrate

CAS No.
138982-67-9
Chemical Name:
Ziprasidone hydrochloride monohydrate
Synonyms
CP-88059-1;Ziprasidong Hcl;ZIPRASIDONE HCL;Ziprasidone HCl hydrate;ZIPRASIDONE INTERMEDIATE;ZIPRASIDONE HYDROCHLORIDE;ZIPRASIDONE HCL MONOHYDRATE;ZIPRASITONE HCl MONOHYDRATE;Geodon Hydrochloride Hydrate;Ziprasidone Hydrochloride (200 mg)
CBNumber:
CB0166832
Molecular Formula:
C21H24Cl2N4O2S
Molecular Weight:
467.41
MDL Number:
MFCD06795476
MOL File:
138982-67-9.mol
MSDS File:
SDS
Last updated:2023-11-02 17:49:29

Ziprasidone hydrochloride monohydrate Properties

Melting point 300°C
storage temp. 2-8°C
solubility DMSO: >10mg/mL
form solid
color Light Orange
Merck 14,10171
BCS Class 2?
CAS DataBase Reference 138982-67-9(CAS DataBase Reference)
FDA UNII 216X081ORU

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Warning
Hazard statements  H317-H373
Precautionary statements  P260-P280
Safety Statements  24/25
RIDADR  UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany  3
RTECS  NM3241200
HS Code  38220010

Ziprasidone hydrochloride monohydrate price More Price(39)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 1724408 Ziprasidone hydrochloride United States Pharmacopeia (USP) Reference Standard 138982-67-9 200mg $436 2024-03-01 Buy
Sigma-Aldrich Y0001286 Ziprasidone hydrochloride monohydrate European Pharmacopoeia (EP) Reference Standard 138982-67-9 $190 2021-12-16 Buy
Sigma-Aldrich Y0001272 Ziprasidone for system suitability 1 European Pharmacopoeia (EP) Reference Standard 138982-67-9 $190 2021-12-16 Buy
Sigma-Aldrich Y0001241 Ziprasidone for system suitability 2 European Pharmacopoeia (EP) Reference Standard 138982-67-9 $190 2021-12-16 Buy
TCI Chemical Z0032 Ziprasidone Hydrochloride Monohydrate >98.0%(HPLC) 138982-67-9 50mg $51 2024-03-01 Buy
Product number Packaging Price Buy
1724408 200mg $436 Buy
Y0001286 $190 Buy
Y0001272 $190 Buy
Y0001241 $190 Buy
Z0032 50mg $51 Buy

Ziprasidone hydrochloride monohydrate Chemical Properties,Uses,Production

Chemical Properties

Pale Tan Powder

Originator

Geodon,Pfizer,USA

Uses

antipsychotic;Dopamine D2/serotonin 5-HT2 antagonist

Uses

Combined serotonin (5HT2) and dopamine (D2) receptor antagonist. Used as an antipsychotic.

Uses

Ziprasidone Hydrochloride is the hydrochloride salt of a benzisothiazolylpiperazine analog structurally related to the atypical antipsychotic drug tiospirone that antagonizes both central serotonin 5-HT2A (Ki = 0.42 nM) and dopamine D2 (Ki = 4.8 nM) receptors. It is also a potent agonist at 5-HT1A receptors (Ki = 3.4 nM), increasing cortical dopamine release which may offset negative effects associated with dopamine D2 antagonism, and an inverse agonist at 5-HT1B and 5-HT1D receptors (pKis = 8.8 and 8.6, respectively).[Cayman Chemical]

Definition

ChEBI: The hydrochloride hydrate salt of ziprasidone.

Manufacturing Process

Preparation of 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro- 1,3-dihydro-2H-indol-2-one
A 20-gallon glass lined tank, under a nitrogen atmosphere, was charged with 33.5 liters of water and 9.4 kilograms (kg) of sodium carbonate (dense, 89.1 moles, 3.4 eq.). The resulting mixture was stirred to give a solution. To the solution 6.4 kg of 2-chloroethyl-6-chloro-oxindole (27.8 moles, 1.06 eq.) was charged, followed by 6.7 kg of 3-piperazinyl-1,2-benzisothiazole hydrochloride (26.2 moles, 1.0 eq.). This was stirred and heated to reflux (100°C). After 11 hours the reaction was sampled for high pressure liquid chromatography (HPLC) assay. The reflux was continued for another 2 hours then the reaction was cooled to 25°C and the slurry stirred for 1 hour. The product was observed and found to be essentially free from lumps and gummy matter. The product was collected by filtration. A 14 liter water was added to the tank and cooled to 12°C and then used to wash the product. The cake was pulled as dry as possible, and the product was returned to the tank along with 40 liters of isopropyl alcohol (IPO). This was cooled and then stirred for 2 hours and the product was collected by filtration. The cake was washed with 13.4 liters of fresh IPO, then dried under vacuum at 30° to 40°C. After drying, 17.3 kg of the title compound was obtained. This was in excess of the theoretical weight yield due to some residual carbonate in the crude product.
Recrystallization of 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6- chloro-1,3-dihydro-2H-indol-2-one
To a clean and dry 100-gallon glass lined tank was charged 9.0 kg of the material obtained above and 86 gallons of tetrahydrofuran (THF). The slurry was heated to reflux and held for 1 hour. The hazy solution was then filtered through a 14" sparkler precoated with filter aid and backed with a Fulflo filter to a clean, dry, and "spec free" glass-lined tank on a lower level. The batch was concentrated by vacuum distillation. Another 8.3 kg of the material obtained in above was dissolved in 83 gallons of THF in the upper tank. This was filtered to the lower tank. The tank lines and sparkler were rinsed with 10 gallons of THF. The batch was concentrated to about 22 gallons, then cooled to 5°C and stirred for 1 hour. The product was collected by filtration. Then 20 gallons of fresh IPO were cooled in the tank and used to rinse the product cake. The product was collected and dried under vacuum at 45°C; yielding 9.05 kg of product (83.8% yield for the coupling and recrystallization. The product matched the spectra of a standard NMR and showed the correct retention time by HPLC with 99.7% assay. Another way for preparation of 5-(2-(4-(1,2-benzisothiazol-3-yl)-piperazinyl)ethyl)-6-chloro-1,3-dihydro-2-H- indol-2-one.
A clean and dry 20-gallon glass lined tank was charged with 19 L of water and 4.44 kg of sodium carbonate, after the carbonate had dissolved 4.29 kg (17.5 moles) of 5-(2-chloroethyl)-6-chloro-oxindole and 3.62 kg (16.5 moles) of 1- (1,2-benzisothiazol-3-yl)piperazine were added. The aqueous slurry was heated to reflux and the temperature maintained for 14 hours. When the reaction was complete the solution was cooled to 20°C and filtered. The wet product was reslurried in 23 L of isopropyl alcohol at room temperature for 2 hours. The product was collected by filtration on 2 large Buchner funnels, each was washed with 3.4 L of fresh isopropyl alcohol. The product was vacuum dried at 30° to 40°C. until no isopropyl alcohol remained, giving 5.89 kg (86.4% yield) of the desired free base which matched a standard sample by high performance liquid chromatography (HPLC).
A clean and dry 20-gallon reactor was charged with 17.4 gallons of deionized water and 4.44 L of concentrated hydrochloric acid, to give a 0.77 M solution. To the solution was added 4.44 kg of the anhydrous Ziprasidone free base. The slurry was warmed to 65°C and held for 18 hours. The slurry was cooled to room temperature. The product was filtered and washed with 2x5-gallon portions of deionized water, and then air dried at 50°C for 30 hours. The dried product contained 4.4% water and the x-ray diffraction method confirmed that the desired product was obtained.

brand name

Geodon (Pfizer).

Therapeutic Function

H-Indol-2-one, 5-(2-(4-(1,2-benzisothiazol-3-yl)-1- piperazinyl)ethyl)-6-chloro-1,3-dihydro-, monohydrochloride monohydrate

Biological Activity

Atypical antipsychotic that displays combined serotonin and dopamine receptor antagonism. Displays high affinity at 5-HT 2A receptors with a 5-HT 2A /D 2 affinity ratio greater than any other clinically available atypical antipsychotics (pK i values are 9.38, 8.88, 8.69, 8.47, 8.32, 8.14, 7.98, 7.49, 7.33 and 6.28 for 5-HT 2A , 5-HT 2C , 5-HT 1D , 5-HT 1A , D 2 , D 3 , α 1 , D 4 , H 1 and D 1 receptors respectively).

Biochem/physiol Actions

Ziprasidone (CP-88059) hydrochloride monohydrate is an orally active combined 5-HT and dopamine receptor antagonist. Ziprasidone hydrochloride monohydrate has affinities for Rat D2 (Ki=4.8 nM), 5-HT2A (Ki=0.42 nM) and 5-HT1A (Ki=3.4 nM).

Biochem/physiol Actions

Ziprasidone is an atypical antipsychotic; FDA approved for the treatment of schizophrenia.

in vitro

Ziprasidone hydrochloride monohydrate (0-500 nM, 150 seconds) blocks wild-type hERG current.

in vivo

Ziprasidone hydrochloride monohydrate (oral gavage; 20 mg/kg; once daily; 7 weeks) results in weight loss, low level physical activity, high resting energy expenditure and greater capacity for thermogenesis when subjected to cold.

storage

Room temperature

Ziprasidone hydrochloride monohydrate Preparation Products And Raw materials

Global( 324)Suppliers
Supplier Tel Email Country ProdList Advantage
Xiamen Wonderful Bio Technology Co., Ltd.
+8613043004613 Sara@xmwonderfulbio.com China 305 58
Nantong Guangyuan Chemicl Co,Ltd
+undefined17712220823 admin@guyunchem.com China 616 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512 info@tianfuchem.com China 21703 55
Hangzhou FandaChem Co.,Ltd.
008657128800458; +8615858145714 fandachem@gmail.com China 9359 55
career henan chemical co
+86-0371-86658258 sales@coreychem.com China 29919 58
Hubei Jusheng Technology Co.,Ltd.
18871490254 linda@hubeijusheng.com CHINA 28180 58
Xiamen AmoyChem Co., Ltd
+86-592-6051114 +8618959220845 sales@amoychem.com China 6387 58
Chongqing Chemdad Co., Ltd
+86-023-61398051 +8613650506873 sales@chemdad.com China 39916 58
Alchem Pharmtech,Inc.
8485655694 sales@alchempharmtech.com United States 63711 58
CONIER CHEM AND PHARMA LIMITED
+8618523575427 sales@conier.com China 47464 58

View Lastest Price from Ziprasidone hydrochloride monohydrate manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Ziprasidone hydrochloride monohydrate pictures 2024-03-08 Ziprasidone hydrochloride monohydrate
138982-67-9
US $10.00 / kg 1kg 99% 1000kg Nantong Guangyuan Chemicl Co,Ltd
Ziprasidone Hydrochloride Monohydrate pictures 2024-01-18 Ziprasidone Hydrochloride Monohydrate
138982-67-9
US $15.00 / kg 1kg 99.98% 8000 Xiamen Wonderful Bio Technology Co., Ltd.
5-[2-[4-(1,2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride USP/EP/BP pictures 2021-07-24 5-[2-[4-(1,2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride USP/EP/BP
138982-67-9
US $1.10 / g 1g 99.9% 100 Tons min Dideu Industries Group Limited

Ziprasidone hydrochloride monohydrate Spectrum

Ziprasidone (hydrochloride hydrate) 5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one hydrochloride hyd Ziprasidone for system suitability 2 Ziprasidone for system suitability 1 ZIPRASIDONE HCL ZIPRASIDONE HYDROCHLORIDE ZIPRASIDONE HYDROCHLORIDE MONOHYDRATE 5-[2-[4-(1,2-BENZISOTHIAZOL-3YL)-1-PIPERAZINYL]ETHYL]-6-CHLORO-1,3-DIHYDRO-2H-INDOL-2-ONE, HYDROCHLORIDE MONOHYDRATE CP-88059-1 5-[2-[4-(1,2-benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2h-indol-2-one hydrochloride Ziprasidong Hcl 5-[2-[4-(1,2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one, Hydrochloride Monohydrate, CP-88059-1 2H-Indol-2-one, 5-2-4-(1,2-benzisothiazol-3-yl)-1-piperazinylethyl-6-chloro-1,3-dihydro-, monohydrochloride, monohydrate ZIPRASIDONE INTERMEDIATE ZIPRASIDONE HCL MONOHYDRATE ZIPRASITONE HCl MONOHYDRATE CP-88059, Geodon, 5-[2-[4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one monohydrate hydrochloride Ziprasidone monohydrate hydrochloride 5-[2-[4-(1,2-Benzisothiazol-3-y1)-1-piperazinyl]ethyl]-6-chlom-1,3-dihydro-2H-indol-2-one 2H-Indol-2-one, 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-, hydrochloride, hydrate (1:1:1) Ziprasidone Hydrochloride Monohydrate Also see: G364400 Ziprasidone Hydrochloride (200 mg) Geodon Hydrochloride Hydrate 5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one hydrochloride hydrat 5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one hydrochloride hydrate Ziprasidone Hydrochloride Mohydrate Ziprasidone hydrochloride monohydrate, 99%, a novel and potent dopamine and serotonin (5-HT) receptor antagonist 5-(2-(4-(1,2-Benzisothiazol-3-yl)Piperazin-1-yl)Ethyl)-6-Chloroindolin-2-One Hydrochloride Hydrate Ziprasidone HCl hydrate Ziprasidone hydrochloride monohydrate CRS Ziprasidone Hydrochloride Monohydra Ziprasidone hydrochloride solution 5-[2-[4-(1,2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride USP/EP/BP Ziprasidone Hydrochloride Monohydrate DISCONTINUED 2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1 3-dihydro-2H-indol-2-one hydrochloride 138982-67-9 5-[2-[4-(1,2-Benzisothiazol-3yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-indol-2-one hydrochloride Ziprasidone Hydrochloride (1724408) 5-[2-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]ethyl]-6-chloro-1,3-dihydro-2H-Indol-2-one hydrochloride hydrate (1:1:1) 138982-67-9 C21H21ClN4OSH2OHCl C21H21ClN4OSClHH2O C21H21ClN4OSHClC21H22Cl2N4OS C21H24Cl2N4O2S C21H21ClN4OSHClC21H22Cl2N4 C21H21ClN4OSHCl C21H21ClN4OS C21H21ClN4OSHClH2O C21H22Cl2N4OS Other APIs APIs Intermediates & Fine Chemicals Pharmaceuticals Heterocycles Pfizer compounds Sulfur & Selenium Compounds 138982-67-9