146939-27-7
Ziprasidone
CAS: 146939-27-7
Molecular Formula: C21H21ClN4OS
146939-27-7 - Names and Identifiers
| Name | Ziprasidone |
| Synonyms | Geodon Ziprasidone ZIPRASIDONE-D8 Ziprasidone HBr 5-{2-[4-(1,2-benzothiazol-3-yl)piperazin-1-yl]ethyl}-6-chloro-2,3-dihydro-1H-indol-2-one -(2-(4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one 5-(2-(4-(1,2-Benzisothiazol-3-yl)-1-piperazinyl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one 1,2-Benzisothiazole, 3-(1-piperazinyl)-, monohydrochlorideH-indol-2-one, 6-chloro-5-(2-chloroethyl)-1,3-dihydro |
| CAS | 146939-27-7 |
| EINECS | 203-794-9 |
| InChI | InChI=1/C21H21ClN4OS/c22-17-13-18-15(12-20(27)23-18)11-14(17)5-6-25-7-9-26(10-8-25)21-16-3-1-2-4-19(16)28-24-21/h1-4,11,13H,5-10,12H2,(H,23,27)/i7D2,8D2,9D2,10D2 |
146939-27-7 - Physico-chemical Properties
| Molecular Formula | C21H21ClN4OS |
| Molar Mass | 412.94 |
| Density | 1.369±0.06 g/cm3(Predicted) |
| Melting Point | 213-215°C |
| Boling Point | 554.8±50.0 °C(Predicted) |
| Solubility | DMSO (Slightly), Methanol (Slightly) |
| Appearance | Solid |
| Color | Brown to Dark Brown |
| Merck | 14,10171 |
| pKa | 13.34±0.20(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.681 |
| Physical and Chemical Properties | Temiparidone hydrochloride: C21H21ClN4OS? HCl? H2O. [138982-67-9]. It also occurs as a hemihydrate with a melting point> 300 °c. |
146939-27-7 - Risk and Safety
| Risk Codes | R60 - May impair fertility R61 - May cause harm to the unborn child R11 - Highly Flammable R19 - May form explosive peroxides R38 - Irritating to the skin |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| RTECS | NM3241000 |
146939-27-7 - Reference Information
| indications | This product is suitable for the treatment of schizophrenia |
| adverse reactions | sleepiness, akathisia, extrapyramidal symptoms, dizziness, dystonia, Head Pain, gastrointestinal discomfort, state of weakness, agitation, high tension. A small number of elevated SGPT, musculoskeletal discomfort, central nervous system abnormalities, rhinitis, maculopapular rash, rubella, abnormal vision, urinary incontinence. |
| drug-related effects | 1. Ziprasidone should not be combined with drugs that prolong the QT interval. 2. Ziprasidone mainly acts on the central nervous system, and should be used with caution when combined with other drugs that act on the central nervous system. 3. Ziprasidone may induce hypotension and therefore may enhance the efficacy of certain antihypertensive drugs. 4. Ziprasidone may antagonize the effects of L-dopamine and dopamine agonists. The effect of carbamazepine on the alignment of other drugs with lasidone: Carbamazepine is an inducer of CYP3A4, and taking 200mg carbamazepine twice a day for 21 consecutive days reduced the AUC of ziprasidone by approximately 35%. The higher the carbamazepine dose, the more the AUC of ziprasidone decreased. |
| pharmacological drug toxicity | ziprasidone is an atypical antipsychotic, its structure is different from that of phenothiazines or butyrylbenzenes. In vitro studies have shown that ziprasidone has high affinity for dopamine D2, D3, 5-hydroxytryptamine 5HT2A, 5HT2C, 5HT1A, 5HT1D, intermediate affinity for the histamine H1 receptor and no affinity for other tested receptors/binding sites including the M cholinergic receptor. Ziprasidone has an antagonistic effect on D2, 5HT2A, 5HT1D receptors and an agonistic effect on 5HT1A receptors. Ziprasidone inhibits synaptic reuptake of serotonin and norepinephrine. |
| atypical antipsychotics | ziprasidone is an atypical antipsychotics belonging to the benzothiazole piperazine class, in vitro, the goods on dopamine D2, D3, 5-HT2A, 5-HT2C, 5-HT1A, 5-HT1D and Alpha 1 adrenergic receptor affinity is strong; The affinity of histamine H1 receptor medium. It has antagonistic effect on dopamine D1, D2, 5-HT2A, 5-HT1D and agonistic effect on 5-HT1A receptor. This product inhibits the reuptake of 5-HT and norepinephrine by presynaptic membrane. The mechanism of action is not clear, it may be through the combined antagonism of dopamine D2 and 5-HT2 to produce anti schizophrenia effect, its blocking intensity is similar to risperidone and haloperidol, and is stronger than olanzapine, quetiapine and clozapine, mainly used for acute or chronic, primary or recurrent schizophrenia, schizophrenia negative, positive symptoms are effective. In particular, the effect of negative symptoms is better. It can reduce hallucinations, delusions, thinking and abnormal action and other positive symptoms; But also improve the emotional monotony, the will of the sex to reduce the negative symptoms. atypical antipsychotics, also known as new generation antipsychotics, are antipsychotics that block dopamine D2 receptors less than 5-HT2A receptors, such as the current clinical use of clozapine, risperidone, olanzapine, quetiapine, ziprasidone and other drugs are such. Atypical antipsychotics in addition to the clinical application of clozapine earlier (70 years), the other are the late 90 years of the emergence of new antipsychotic drugs. atypical antipsychotics not only block dopamine D2 receptors, but also have a stronger effect of blocking 5-HT2A receptors. When blocking the midbrain-limbic pathway dopamine D2 receptors, can improve the patient's positive symptoms; When blocking the midbrain-cortical pathway on the presynaptic membrane of 5-HT2A receptors, can cause the release of dopamine, excites dopamine D1 receptor in dorsolateral prefrontal cortex, improves negative and cognitive symptoms, excites dopamine D1 receptor in medial prefrontal cortex and orbit, and improves depressive symptoms; when blocking 5-HT2A receptors on the presynaptic membrane of the substantia nigra-striatal pathway causes a deinhibitory release of dopamine, which may partially counteract the blockade of dopamine D2 receptors by the drug, therefore, the extrapyramidal reaction is mild (long-term use is not easy to cause tardive dyskinesia); When blocking the 5-HT2A receptor on the presynaptic membrane of the hypothalamus-funnel part, it causes the deinhibitory release of dopamine, partial counteraction of the drug on dopamine D2 receptor blockade, so Hyperprolactinemia is not obvious. Such as clozapine, olanzapine, quetiapine and ziprasidone. |
| dosage and usage | the initial dose is 20mg twice daily, orally. General bioavailability of 30%; With food with the service can increase the absorption of this product 1 times, bioavailability of 60%; With high fat meal service, the bioavailability of up to 97%. The dose may be adjusted after 2 days, typically twice daily, in a dose range of 20 to 80mg, with a maximum dose of 100mg. Patients with mild to moderate liver and kidney damage can not adjust the dose. Ziprasidone is mainly metabolized in the liver, and the metabolites are mainly excreted in the urine and partially in the feces. Terminal T1/2 is about 7H. |
| Use | neuroleptics. Dopamine d2-serotonin 5-HT2 antagonist. |
| production method | 6-chloro-1, 3-dihydro-2h-indol-2-one (I) and bromoacetic acid in polyphosphoric acid, acylation reaction to obtain compound (II). Further, the mixture was stirred with triethyl Silicon hydride and trifluoroacetic acid at room temperature to obtain compound (III). Finally, N-(3-benzisothiazolyl) piperazine was reacted in MIBK containing sodium carbonate. The product was obtained. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:04:16
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