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Ziprasidone hydrochloride monohydrate

Product Name
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
Formula Weight
467.41
MOL File
138982-67-9.mol
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Ziprasidone hydrochloride monohydrate Property

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)
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Safety

Safety Statements 
24/25
RIDADR 
UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 
3
RTECS 
NM3241200
HS Code 
38220010
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H317May cause an allergic skin reaction

H373May cause damage to organs through prolonged or repeated exposure

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
1724408
Product name
Ziprasidone hydrochloride
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$436
Updated
2024/03/01
Sigma-Aldrich
Product number
Y0001286
Product name
Ziprasidone hydrochloride monohydrate
Purity
European Pharmacopoeia (EP) Reference Standard
Price
$190
Updated
2021/12/16
Sigma-Aldrich
Product number
Y0001272
Product name
Ziprasidone for system suitability 1
Purity
European Pharmacopoeia (EP) Reference Standard
Price
$190
Updated
2021/12/16
Sigma-Aldrich
Product number
Y0001241
Product name
Ziprasidone for system suitability 2
Purity
European Pharmacopoeia (EP) Reference Standard
Price
$190
Updated
2021/12/16
TCI Chemical
Product number
Z0032
Product name
Ziprasidone Hydrochloride Monohydrate
Purity
>98.0%(HPLC)
Packaging
50mg
Price
$51
Updated
2024/03/01
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Ziprasidone hydrochloride monohydrate Chemical Properties,Usage,Production

Chemical Properties

Pale Tan Powder

Originator

Geodon,Pfizer,USA

Uses

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

Uses

antipsychotic;Dopamine D2/serotonin 5-HT2 antagonist

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

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).

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

Raw materials

Preparation Products

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Ziprasidone hydrochloride monohydrate Suppliers

Jiangsu Nhwa Pharmaceutical Co., Ltd.
Tel
0516-83827110
Fax
+86 (516) 8776-9782
Email
nhwa@nhwa-group.com
Country
China
ProdList
102
Advantage
50
Hunan Revel Biotechnology Co. , Ltd.
Tel
19359985961 19359985961
Email
2430503320@qq.com
Country
China
ProdList
1469
Advantage
58
Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
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55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
Advantage
76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
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Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44688
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Pure Chemistry Scientific Inc.
Tel
001-857-928-2050 or 1-888-588-9418
Fax
001-617-206-9595
Email
sales@chemreagents.com
Country
United States
ProdList
10186
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LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Nanjing Chemlin Chemical Co., Ltd
Tel
025-83697070
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
19179
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64
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
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View Lastest Price from Ziprasidone hydrochloride monohydrate manufacturers

Jinan Million Pharmaceutical Co., Ltd
Product
Ziprasidone hydrochloride monohydrate 138982-67-9
Price
US $1.00/kg
Min. Order
0.10000000kg
Purity
99%
Supply Ability
200KG
Release date
2024-07-26
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Product
Ziprasidone Hydrochloride 138982-67-9
Price
US $0.00/g
Min. Order
1g
Purity
More Than 99%
Supply Ability
100kg/Month
Release date
2024-10-11
Hebei Ganmiao New material Technology Co., LTD
Product
Ziprasidone hydrochloride monohydrate 138982-67-9
Price
US $10.00-7.00/kg
Min. Order
1kg
Purity
99.9%
Supply Ability
20ton
Release date
2024-06-07

138982-67-9, Ziprasidone hydrochloride monohydrateRelated Search:


  • 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
  • Ziprasidone Hydrochloride Mohydrate
  • Ziprasidone hydrochloride monohydrate, 99%, a novel and potent dopamine and serotonin (5-HT) receptor antagonist
  • 5-(2-(4-(Benzo[d]isothiazol-3-yl)piperazin-1-yl)ethyl)-6-chloroindolin-2-one hydrochloride hydrate
  • 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