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| Targets |
6-Chlorooxindole is a synthetic building block and does not have a direct biological target. As an intermediate, it is used to construct the oxindole moiety of Ziprasidone, an atypical antipsychotic. Ziprasidone acts as an antagonist at dopamine D2 and serotonin 5-HT2A receptors, as well as a partial agonist at 5-HT1A, contributing to its antipsychotic efficacy. The chlorooxindole intermediate is not pharmacologically active itself; its role is purely synthetic.
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| ln Vitro |
6-Chlorooxindole itself does not exhibit direct biological activity as a drug. It is a chemical intermediate, not an active pharmaceutical ingredient (API). It is not typically evaluated in enzyme inhibition or cell-based assays. The compound's importance lies in its utility for the synthesis of Ziprasidone, which has well-documented in vitro activity as a dopamine D2 and serotonin 5-HT2A receptor antagonist, with Ki values in the low nanomolar range.
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| ln Vivo |
No direct in vivo activity data for 6-Chlorooxindole is available. The final drug Ziprasidone, synthesized from this intermediate, is FDA-approved for the treatment of schizophrenia and bipolar disorder. Ziprasidone is administered orally (20-80 mg twice daily) or intramuscularly. In animal models, Ziprasidone (1-10 mg/kg, IP or PO) has shown antipsychotic activity in conditioned avoidance response tests and inhibition of apomorphine-induced climbing behavior. The intermediate has no in vivo activity.
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| Enzyme Assay |
6-Chlorooxindole is not a biologically active compound; it is a chemical intermediate characterized by physical and chemical methods. Purity is assessed by GC (>98%), and identity is confirmed by ¹H NMR and ¹3C NMR spectroscopy (in DMSO-d₆) and mass spectrometry (EI-MS, expected m/z 167/169 [M]+, Cl isotope pattern). Melting point (195-199degC) is a key quality parameter. The compound is not tested in biological assays.
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| Cell Assay |
No standard cell-based protocol for 6-Chlorooxindole exists. For toxicity screening, the compound can be tested in a standard in vitro cytotoxicity assay: HepG2 or HEK293 cells are seeded in 96-well plates (1×10⁴ cells/well) and incubated overnight. 6-Chlorooxindole is added at concentrations of 0.1-1000 microM (DMSO ≤0.1%) for 24-72 h. Cell viability is measured by MTT assay. The CC₅0 is typically >100 microM, indicating low cytotoxicity. This is for safety assessment only, not for pharmacological evaluation.
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| Animal Protocol |
No in vivo animal protocol for 6-Chlorooxindole exists, as it is not a drug. For the final drug Ziprasidone, in vivo testing is performed in animal models of psychosis: Male Sprague-Dawley rats (200-300 g) are administered Ziprasidone (1-10 mg/kg, IP or PO) 30-60 min before testing. The conditioned avoidance response (CAR) test measures the ability of the drug to inhibit avoidance behavior (escape vs. avoidance). The apomorphine-induced climbing test (apomorphine 0.5-1 mg/kg SC) measures inhibition of climbing behavior in mice (0.5-2 mg/kg IP). The intermediate is not used in these studies.
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| ADME/Pharmacokinetics |
Not applicable; 6-Chlorooxindole is a chemical intermediate, not a drug. Physicochemical properties: MW 167.59, Log P ~2.0, melting point 195-199degC, insoluble in water, soluble in organic solvents (DMSO, DCM, ethanol). It is not intended for absorption or systemic distribution. In the synthetic route to Ziprasidone, it is reacted with other building blocks to form the final API.
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| Toxicity/Toxicokinetics |
For 6-Chlorooxindole, hazard statements: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation). Signal word: Warning. Precautionary statements: P261 (Avoid breathing dust), P280 (Wear protective gloves/eye protection), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes). Store in a cool, dry place (room temperature, <15degC). Avoid formation of dust and inhalation. Not for human consumption.
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| References | |
| Additional Infomation |
6-Chlorooxindole (CAS# 56341-37-8) is a research-grade chemical intermediate used in the synthesis of the antipsychotic drug Ziprasidone (Geodon, FDA-approved for schizophrenia and bipolar disorder). It is not an FDA-approved drug itself. The compound is for research and industrial synthesis use only, not for diagnostic or therapeutic applications.
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| Molecular Formula |
C8H6CLNO
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|---|---|
| Molecular Weight |
167.59
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| Exact Mass |
167.014
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| CAS # |
56341-37-8
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| PubChem CID |
736344
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| Appearance |
Solid powder
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| Hydrogen Bond Donor Count |
1
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
11
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| Complexity |
183
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1C2=C(C=C(C=C2)Cl)NC1=O
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| InChi Key |
CENVPIZOTHULGJ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H6ClNO/c9-6-2-1-5-3-8(11)10-7(5)4-6/h1-2,4H,3H2,(H,10,11)
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| Chemical Name |
6-chloro-1,3-dihydroindol-2-one
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.9669 mL | 29.8347 mL | 59.6694 mL | |
| 5 mM | 1.1934 mL | 5.9669 mL | 11.9339 mL | |
| 10 mM | 0.5967 mL | 2.9835 mL | 5.9669 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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