(1S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 1H-indole-3-carboxylate
Tropisetron
CAS: 89565-68-4
Molecular Formula: C17H20N2O2
(1S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 1H-indole-3-carboxylate - Names and Identifiers
| Name | Tropisetron |
| Synonyms | icf205-930 TROPISETRON Tropisetron Tropisetron (ICS 205930) 3-TROPANYL-INDOLE-3-CARBOXYLATE METHIODI DE ICS-205,930, METHIODI 3-TROPANYL-INDOLE-3-CARBOXYLATE HYDROCHL ORIDE(ICS-205,930, NOVOBAN (1S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 1H-indole-3-carboxylate (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 1H-indole-3-carboxylate 8-methyl-8-azabicyclo(3.2.1)oct-3-ylester,endo-1h-indole-3-carboxylicaci 1H-Indole-3-carboxylic acid, endo-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester 1H-Indole-3-carboxylic acid (1β,5β)-8-methyl-8-azabicyclo[3.2.1]octan-3α-yl ester |
| CAS | 89565-68-4 |
| EINECS | 1806241-263-5 |
| InChI | InChI=1/C17H20N2O2/c1-19-11-6-7-12(19)9-13(8-11)21-17(20)15-10-18-16-5-3-2-4-14(15)16/h2-5,10-13,18H,6-9H2,1H3/t11-,12+,13+ |
(1S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 1H-indole-3-carboxylate - Physico-chemical Properties
| Molecular Formula | C17H20N2O2 |
| Molar Mass | 284.35 |
| Density | 1.26 |
| Melting Point | 201-202 °C |
| Boling Point | 448.5±35.0 °C(Predicted) |
| Solubility | H2O: soluble |
| Appearance | solid |
| Color | white |
| pKa | 15.38±0.30(Predicted) |
| Storage Condition | Inert atmosphere,2-8°C |
| Refractive Index | 1.644 |
| Physical and Chemical Properties | Crystallization, melting point 201-202 ℃ (dichloromethane-ethyl acetate). Tropisetron monohydrochloride (Tropisetron Monohydroehloride):C17H20N2O2?HCI. [105826-92-4]. Melting point 283-285 ℃ (decomposition). |
| Use | Serotonin antagonist |
(1S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 1H-indole-3-carboxylate - Risk and Safety
| WGK Germany | 3 |
(1S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 1H-indole-3-carboxylate - Nature
Open Data Verified Data
dichloromethane a crystallization in ethyl acetate, melting point of 201~202 deg C.
Last Update：2024-01-02 23:10:35
(1S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 1H-indole-3-carboxylate - Preparation Method
Open Data Verified Data
indole -3 formic acid is dissolved in toluene, thionyl chloride is added, Reflux reaction is stirred, part of toluene is distilled out, toluene solution reaction is slowly added Tol at 50 ℃, toluene is distilled out, cooling, adding ethyl acetate and water, stirring, Dropwise adding ammonia to adjust the pH value, separating the organic layer, drying and distilling out ethyl acetate; The obtained material is dissolved in ethanol, hydrogen chloride gas is introduced to pH 3, filtered, tropisetron was obtained by concentration and cooling.
Last Update：2022-01-01 09:23:25
(1S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 1H-indole-3-carboxylate - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 3.517 ml | 17.584 ml | 35.168 ml |
| 5 mM | 0.703 ml | 3.517 ml | 7.034 ml |
| 10 mM | 0.352 ml | 1.758 ml | 3.517 ml |
| 5 mM | 0.07 ml | 0.352 ml | 0.703 ml |
Last Update：2024-01-02 23:10:35
(1S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 1H-indole-3-carboxylate - Use
Open Data Verified Data
developed by Sandoz, Switzerland, was launched in 1992. There are potent and selective 5-HT3 receptor antagonists. This reflex can selectively inhibit the excitation of presynaptic 5-HT3 receptors of the peripheral nervous system and possibly 5-HT of the central nervous system. It is a highly selective inhibitor of 5-HT3 receptors in peripheral neurons and central nervous system. It has therapeutic effect on Vomit caused by chemotherapy and radiotherapy.
Last Update：2022-01-01 09:23:25
(1S,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl 1H-indole-3-carboxylate - Reference Information
| clinical evaluation | Sorbe and other reports of this product on cisplatin (dose 50~89mg/m2) the complete control rate of chemotherapy-induced acute exacerbation Vomit was 63%. 58 cases of malignant tumor chemotherapy-induced Nausea, vomiting, tropisetron or ondansetron 8mg in the same patients before and after 2 cycles of chemotherapy in the first day before the administration of intravenous injection 30min, and dexamethasone 10mg intravenous infusion. Results the efficacy of the two drugs in the control of acute and delayed Nausea and Vomit were basically similar, both could reach 81% ~ 100%. This product has prominent antiemetic effect on the strong emetic chemotherapy drug cisplatin. |
| drug-related effects | diet can slightly prolong the absorption of this product. This product and rifampicin, phenobarbital and other liver enzyme inducing drugs used at the same time, can speed up the metabolism, so fast metabolic type need to increase the dose, slow is not necessary. Cimetidine and other liver enzyme inhibitors had no significant effect on the plasma concentration of this product. |
| indication | tropisetron is clinically used for the prevention and treatment of cancer induced by chemotherapy in Nausea and Vomit. |
| Use | a potent and selective 5-HT3 receptor antagonist. For chemotherapy-induced Vomit. 5-hydroxytryptamine antagonist |
| production method | tropisetron can be obtained by reacting Tol (I) and acyl chloride (II). |
Last Update：2024-04-09 21:01:54
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