Zuclopenthixol
Zuclopenthixol
CAS: 53772-83-1
Molecular Formula: C22H25ClN2OS
Zuclopenthixol - Names and Identifiers
| Name | Zuclopenthixol |
| Synonyms | Clopixol Zuclopentixol Zuclopenthixol Unii-47isu063sg UNII-47ISU063SG Einecs 258-758-5 cis-Clopenthixol Zuclopenthixolum Clopentixol cis-(Z)- Zuclopentixol [Spanish] Zuclopenthixolum [Latin] (Z)-4-(3-(2-Chlorothioxanthen-9-ylidene)propyl)-1-piperazineethanol 4-[3-[(Z)-2-Chloro-9H-thioxanthen-9-ylidene]propyl]-1-piperazineethanol 2-{4-[3-(2-chloro-9H-thioxanthen-9-ylidene)propyl]piperazin-1-yl}ethanol 4-[3-[(9Z)-2-Chloro-9H-thioxanthene-9-ylidene]propyl]-1-piperazineethanol 2-{4-[(3Z)-3-(2-chloro-9H-thioxanthen-9-ylidene)propyl]piperazin-1-yl}ethanol |
| CAS | 53772-83-1 |
| EINECS | 258-758-5 |
| InChI | InChI=1/C22H25ClN2OS/c23-17-7-8-22-20(16-17)18(19-4-1-2-6-21(19)27-22)5-3-9-24-10-12-25(13-11-24)14-15-26/h1-2,4-8,16,26H,3,9-15H2/b18-5- |
Zuclopenthixol - Physico-chemical Properties
| Molecular Formula | C22H25ClN2OS |
| Molar Mass | 400.96 |
| Density | 1.289±0.06 g/cm3(Predicted) |
| Melting Point | 56-60°C |
| Boling Point | 577.4±50.0 °C(Predicted) |
| Flash Point | 303°C |
| Solubility | Chloroform (Slightly), Methanol (Slightly) |
| Vapor Presure | 3.56E-14mmHg at 25°C |
| Appearance | Solid |
| Color | White to Off-White |
| pKa | 14.96±0.10(Predicted) |
| Storage Condition | -20°C Freezer, Under Inert Atmosphere |
| Refractive Index | 1.675 |
Zuclopenthixol - Reference Information
| Overview | Zhuchlorothiol is a thioanthracene derivative, which is the cis isomer of clopentixol. It works by blocking dopamine receptors and has significant antipsychotic effects and specific sedative effects. It is especially suitable for patients with schizophrenia. It has the effect of anti-stereotype caused by methylphenidate and has the effect of anti-apomorphine, this product can inhibit conditional avoidance response and rigidity, and is 10 times stronger than chlorpromazine. The acute toxicity and chronic toxicity of ziclothiam are low, and no toxicity is found under the treatment dose; there is no toxicity that needs special attention when using it for women of childbearing age; no toxicity such as mutagenicity and carcinogenicity, however, there are occasional extrapyramidal reactions, dyskinesia, akathisia, gastrointestinal function and cardiac conduction disorders, saliva and sweat gland secretion disorders, cholestasis, seizures, corneal or crystalline opacity, amenorrhea, galactorrhea, etc., and fatigue is prone to appear at the beginning of medication. Trichlorothiol has a weak anticholinergic effect and a strong antihistamine effect. It can inhibit conditional avoidance reactions and rigidity. It is suitable for the treatment of psychosis with anxiety and hallucination symptoms, paranoia-hallucinogenic schizophrenia, adolescent dementia, mania and anxiety Periodic psychosis; anxiety, excitement, confusion, brain atrophy caused by mental factors, post-traumatic psychosis, tremor delirium, etc., especially suitable for elderly patients, it has been listed in more than 30 countries including Europe, Latin America, Canada, and Mexico. |
| Pharmacological action | Trichlorothiol is a thioanthracene antipsychotic, which works by blocking dopamine receptors. It can resist the stereotyped symptoms caused by methylphenidate, and its effect is stronger than chlorpromazine; the anti-apomorphine effect is the same as haloperidol; it can inhibit the conditional avoidance response, and the effect is stronger than chlorpromazine; there are also anticholinergic and antihistamine Effects, but the anticholinergic effect is weak, and the antihistamine effect is strong. |
| flupentixol anti-schizophrenia | flupentixol is a safe and efficient thioanthracene anti-schizophrenia drug, which blocks D2 receptors It exerts a strong antipsychotic effect, which is 4-8 times that of clopentixol, while its sedative effect is weak, and it has anti-anxiety and anti-depression effects. Oral tablets reached a peak in 4 hours and t1/2 was 35 hours. The blood peak concentration of the decanoate preparation can be maintained for about 7 days after injection, t1/2 is 19 days, and the bioavailability of the drug is 40%. It is suitable for the treatment of acute and chronic schizophrenia; it has a good effect on the thinking and perceptual disorders (such as delusions, hallucinations) of schizophrenia, and can improve the symptoms of patients with chronic diseases. Long-term medication can prevent the recurrence of symptoms in convalescent patients; Its long-acting preparation is suitable for the maintenance treatment of chronic schizophrenia. A small dose has a stable mood, antidepressant and anti-anxiety effect, and can be used for depression and depressive neurosis; in addition, it is effective for epilepsy, senile dementia, mental retardation, and alcohol dependence with mental symptoms; it can also be used for manic episodes of mania and bipolar disorder, and can quickly control symptoms such as excitement, restlessness, and multiple languages; It can also be used for paranoid psychosis, brain atrophy and mental disorders after trauma. The main adverse reactions of flupentixol are extrapyramidal symptoms, manifested as increased muscle tone, tremor, and akathisia; occasionally, dry mouth, constipation, dizziness and insomnia, and no significant toxicity to the heart, liver, kidney, and hematopoietic system. Patients with severe heart, liver, kidney and other organ or system diseases, patients with acute alcohol, barbiturate, opioid poisoning and coma, circulatory failure, cachexia, pheochromocytoma, and those who are allergic to any of the ingredients in this product are prohibited. |
| pharmacokinetics | 3~6h after oral administration, the highest serum concentration was reached, and the absolute bioavailability was 25%. The body distribution volume of this product and its metabolites is similar to other sedatives. The concentration is high in the liver, lung, intestine and kidney, and the concentration is much lower in the brain. This product is mainly metabolized by oxidation on sulfur, dealkylation on nitrogen in the side chain and binding to glucuronide, and is not isomerized in organs. Most of this product is excreted from urine and feces; a small amount is excreted from the kidneys. The half-life of serum clearance is about 20h. |
| synthesis route | 1) preparation of 2-chloro -9-allyl -9-thioxanol: dissolve 10.00g (0.405mol) 2-chloro -9-thioxanone in 600mL tetrahydrofuran, stir at 20-30 ℃, then add 26g of magnesium powder, 1g of iodine, and drop 65g(0.855mol) of allyl chloride, react at 40 ℃-50 ℃ for 2 hours, drop 1000ml of 20% sodium chloride aqueous solution into the reaction solution after cooling, stir for 10min, filter the insoluble matter, then extract twice with dichloromethane, 500ml each time, combine organic phases, wash with 500ml of water, separate organic layers, filter after drying, concentrate the filtrate to remove the solvent, and obtain 105.40g of 2-chloro -9-allyl -9-thiol. 2) Preparation of 2-chloro -9-(2-propenyl) thioxanol: Dissolve 100.00g (0.346mol) 2-chloro -9-allyl -9-thioxanol in 100ml of toluene, heat the solution to 40 ℃, dissolve 1.34g(0.017mol) of acetyl chloride in 41.19g(0.403mol) of acetic anhydride and add drops to the above solution, the temperature is controlled at about 40 ℃, the dripping is completed, the reaction temperature is heated to 50 ℃-55 ℃ until TLC monitors the reaction is complete, and the solvent is steamed out by decompression concentration to obtain 94.01 g2-chloro -9-(2-propenyl) thioxane. 3) Preparation of chlorothiol: 2-chloro -9-(2-propenyl) thioxane and N-(2-hydroxyethyl) piperazine were added into a 1L four-mouth flask, stirred and heated to 100 ℃ for reaction, and TLC monitored the reaction until the reaction was complete. The vacuum oil pump decompresses and concentrates excess N-(2-hydroxyethyl) piperazine, the temperature is controlled at 100 ℃-135 ℃, and the vacuum degree of the oil pump is 0.2-1mmHg. After distillation, 400ml of benzene and 100ml of water are added to the obtained oil, stirred at 70 ℃ for 15min, separated, then washed the organic phase with 100ml of water, and the temperature is controlled at 60-70 ℃, separated; Extraction, suction filtration, drying of anhydrous sodium sulfate and concentration of filtrate under reduced pressure to obtain 109.32g of chlorothiol. the specific reaction process is as follows: fig. 1 shows the synthesis route of chlorothiol |
| adverse reactions | most adverse reactions are dose-dependent, with the greatest frequency and severity of adverse reactions at the initial stage of treatment, and further treatment can be reduced. 1. Cardiovascular system: orthostatic hypotension, hypotension, tachycardia or palpitations are common. In addition, blood circulation disorders, hematopoietic dysfunction, and heart block can be seen. 2. Mental and nervous system: very common extrapyramidal reactions, especially in the early stages of treatment, including tremor, hypertonia, akathisia, hypokinesia, dystonia, tardive dyskinesia, abnormal gait, acute dyskinesia, eye movement crisis. In addition, drowsiness, insomnia, inattention, depression, dizziness, headache, anxiety, tension, agitation, apathy, forgetfulness, abnormal dreams, loss of appetite, hallucinations, confusion, convulsions, ataxia and seizures can be seen. There are reports of nerve blocker malignant syndrome. 3. Metabolism and endocrine system: common weight gain, weight loss, rare thirst. Another visible saliva secretion disorders. 4. Respiratory system: rare nasal congestion and dyspnea. 5. Musculoskeletal system: extremely common muscle weakness. 6. Urinary system: common urination disorders, menstrual disorders in women, erectile dysfunction in men. Rare male breast development, female non-postpartum lactation, vaginal dryness, amenorrhea, urinary retention. 7. Liver: transient mild changes in liver function, hepatitis, jaundice. 8. Gastrointestinal system: extremely common dry mouth. Increased saliva, constipation, vomiting, diarrhea and nausea are common. Abdominal pain is rare. 9. Skin: common hyperhidrosis, photosensitive reaction, pruritus. Rashes are rare. Can see sweat gland secretion disorder. 10. Eyes: common abnormal visual adjustment, abnormal visual acuity. Visible mydriasis, corneal or crystalline opacity. Other: common pain, rare fainting, fatigue, flushing, allergic reactions, cholestasis. |
| drug interaction | 1. it can increase the effect of alcohol, barbital and other central nervous system inhibitory drugs. 2. It can enhance the effect of antihypertensive drugs. 3. It can weaken the effects of levodopa and epinephrine drugs. 4. The combination of metoclopramide and piperazine can increase the occurrence of extrapyramidal symptoms. 5. When combined with lithium salt, it can cause brain damage, extrapyramidal reaction, and movement disorders. 6. It can affect the effect of insulin and glucose. Diabetic patients should adjust the dose. |
| precautions | 1. patients with convulsive disorder, severe liver disease or cardiovascular disease should use this product with caution. In addition to stopping the drug immediately, the most important thing is to use general supportive therapy and symptomatic treatment. Danttraline may be useful. 3. This product will affect the ability to drive vehicles and operate machines. 4. The use of pregnant and lactating women should be weighed. When this product is used in the third trimester of pregnancy or during delivery, newborns may have symptoms of poisoning. The FDA rated the pregnancy safety of this drug as Class C. 5. No experience in children's medication, children are not recommended to use this product. (2016-04-14) |
| use | for acute and chronic schizophrenia and other psychoses, especially those with hallucinations, delusions, thinking disorders, agitation, restlessness, hostility and aggression. |
| contraindications | patients with acute alcohol, barbiturate, opioid poisoning and coma, circulatory failure, cachexia, pheochromocytoma, and allergy to any component in this product are prohibited. |
Last Update：2024-04-10 22:29:15
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