(2E)-2-[(5-Methoxy-1H-indol-3-yl)methylene]-N-pentylhydrazinecarboximidamide
Tegaserod
CAS: 145158-71-0
Molecular Formula: C16H23N5O
(2E)-2-[(5-Methoxy-1H-indol-3-yl)methylene]-N-pentylhydrazinecarboximidamide - Names and Identifiers
| Name | Tegaserod |
| Synonyms | Zelmac TEGASEROD Tegaserod Tegaserode 145158-71-0 2-[(5-methoxy-1h-indol-3-yl)methylene]-n-pentylhydrazine-carboximidamide Hydrazinecarboximidamide, 2-[(5-methoxy-1H-indol-3-yl)methylene]-N-pentyl- (2E)-2-[(5-Methoxy-1H-indol-3-yl)methylene]-N-pentylhydrazinecarboximidamide (2E)-2-[(5-methoxy-1H-indol-3-yl)methylidene]-N'-pentylhydrazinecarboximidamide hydrazinecarboximidamide, 2-[(5-methoxy-1H-indol-3-yl)methylene]-N-pentyl-, (2E)- |
| CAS | 145158-71-0 |
| InChI | InChI=1/C16H23N5O.C4H4O4/c1-3-4-5-8-18-16(17)21-20-11-12-10-19-15-7-6-13(22-2)9-14(12)15;5-3(6)1-2-4(7)8/h6-7,9-11,19H,3-5,8H2,1-2H3,(H3,17,18,21);1-2H,(H,5,6)(H,7,8)/b20-11+;2-1+ |
(2E)-2-[(5-Methoxy-1H-indol-3-yl)methylene]-N-pentylhydrazinecarboximidamide - Physico-chemical Properties
| Molecular Formula | C16H23N5O |
| Molar Mass | 301.39 |
| Density | 1.18 |
| Melting Point | 155° |
| Boling Point | 470.6±48.0 °C(Predicted) |
| Flash Point | 353.8°C |
| Vapor Presure | 2.15E-18mmHg at 25°C |
| pKa | 15.81±0.30(Predicted) |
| Storage Condition | 2-8°C |
(2E)-2-[(5-Methoxy-1H-indol-3-yl)methylene]-N-pentylhydrazinecarboximidamide - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S36/37 - Wear suitable protective clothing and gloves. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
(2E)-2-[(5-Methoxy-1H-indol-3-yl)methylene]-N-pentylhydrazinecarboximidamide - Nature
Open Data Verified Data
white crystalline powder. Melting point 155 °c.
Last Update：2024-01-02 23:10:35
(2E)-2-[(5-Methoxy-1H-indol-3-yl)methylene]-N-pentylhydrazinecarboximidamide - Preparation Method
Open Data Verified Data
2-nitro-5-methoxytoluene was dissolved in BIS (dimethylamino)-t-butoxymethane, stirred at 90 ° C., concentrated under reduced pressure, and the resulting material was crystallized from methanol, 2-[1 '-(N,N-dimethylamino) ethylene -2'-yl]-4-methoxybenzene was obtained. The compound and Raney nickel were dissolved in toluene and tetrahydrofuran, hydrogenated at room temperature, and treated to give 5 methoxy indole. Under certain conditions, phosphorus oxychloride is added dropwise in dimethylformamide, and then a 5-methoxy indole dimethylformamide solution is added dropwise, and the reaction is stirred at room temperature to obtain 5-methoxy indole -3-formaldehyde. 5-methoxyindole -3-formaldehyde and 1-(N-pentyl) -3-n7-aminoguanidine hydroiodide dissolved in methanol, hydrogen chloride methanol solution reaction, concentration, add acetic acid ethanol, the sodium carbonate solution obtained by treatment is dried, concentrated, and 5-methoxyindole -3 formaldehyde amino (N-pentylamino) methylene hydrazone is obtained by column chromatography. The hydrazone was dissolved in ethanol, Palladium-carbon was added, and the mixture was hydrogenated at 45 ° C. To give Tegaserod.
Last Update：2022-01-01 09:23:33
(2E)-2-[(5-Methoxy-1H-indol-3-yl)methylene]-N-pentylhydrazinecarboximidamide - Use
Open Data Verified Data
developed by Novartis, Switzerland. It was first launched in Mexico in 2001. It was approved for marketing in the United States by FIA in July 2002. Is a 5-HT4 receptor partial agonist that selectively binds to and activates the 5-HT4 receptor in the gastrointestinal tract. Short-term treatment for relieving symptoms of constipation-predominant irritable bowel syndrome (IBS- C) in women. Constipation-predominant irritable bowel syndrome includes Abdominal Pain, abdominal discomfort, flatulence, constipation and other symptoms.
Last Update：2022-01-01 09:23:33
(2E)-2-[(5-Methoxy-1H-indol-3-yl)methylene]-N-pentylhydrazinecarboximidamide - Reference Information
| Overview | Tegaserod maleate is a kind of serotonin derivative amaminoguanidine indole compound, which has been confirmed for the first time to relieve irritable bowel syndrome (IBS)-induced abdominal pain and discomfort, abdominal distension and constipation. It is the first drug in the class of 5-HT4 receptor partial agonists, belonging to gastric motility drugs and antiemetic drugs. It was approved by FDA (National Drug Administration) on July 24, 2002 for short-term treatment of female patients with constipation as the main intestinal symptom (C-IBS). With the in-depth research and understanding of 5-HT4 receptors and their subtypes in the gastrointestinal tract and the clinical application of tegaserol maleate, it is found that tegaserol maleate has a certain therapeutic effect on a variety of gastrointestinal functional diseases. Therefore, it is necessary to study the pharmacological mechanism and clinical efficacy of tegaserod maleate, which provides reference and theoretical basis for clinical effective application, especially in the treatment of gastrointestinal diseases. |
| pharmacological action | 1. promoting gastrointestinal motility tegaserod maleate binds to 5-HT4 receptor with high affinity and then activates 5-HT4 receptor, thus activating adenylate cyclase and increasing cAMP, which in turn activates its dependent protein kinase (PKA), closing the K channel of cell membrane and opening the Ca2 channel, the enhanced Ca2 current can mediate Cl secretion, thereby improving the intestinal secretion function: Cl and H combine to form HCl has the effect of sterilization, promoting pancreatic juice, bile and intestinal secretion, and the formation of acidic circulation is conducive to the absorption of calcium and iron. On the other hand, by triggering the physiological reflex of the intestinal membrane, the intestinal chromaffin cells are stimulated to release calcium gene-related protein (CGRP), vasoactive intestinal peptide (VIP) and substance P (SP), which make the proximal and distal colon contract. Relaxation promotes colon peristalsis, thereby accelerating the passage of colon contents. Therefore, tegaserol maleate can shorten the operation time of the small intestine and colon, treat constipation, increase the frequency of defecation, soften feces, and at the same time improve the patient's gastrointestinal symptoms, such as abdominal pain, abdominal discomfort and abdominal distension. Tegaserod maleate can also promote gastric emptying, and it is more obvious in male patients. 2. improving visceral hypersensitivity visceral hypersensitivity refers to the phenomenon that the threshold of visceral pain or discomfort stimulation is reduced, visceral discomfort to physiological stimulation or strong response to noxious stimulation. The researchers found that small balloon stretch stimulation in the intestinal tract of IBS patients can cause obvious abdominal discomfort. At present, visceral hypersensitivity is considered to be an important pathophysiological mechanism of digestive tract functional diseases. Other patients with functional gastrointestinal diseases (FGID) have also found that the internal organs are highly sensitive to stretch and even to chemical stimuli, and they are also manifested in the abnormal amplification of internal-body pain. Tegaserod maleate also regulates visceral sensation in patients with irritable bowel syndrome (IBS). Studies suggest that tegoserol maleate can regulate mechanical receptors in the rectal wall of cats and reduce the sensitivity of afferent fibers. A number of clinical studies have shown that tegazerol maleate can improve abdominal pain symptoms in patients with IBS, reduce signal afferent during rectal dilation, and reduce abdominal tension and pain caused by this [6]. In addition, tegazerol maleate can improve gastric hyper-receptive diastolic function in FD patients, increase the sensory threshold and pain 1-7 value of gastric volume stimulation in patients with functional heartburn; patients with functional heartburn can tolerate greater volume and pressure stimulation in the esophageal cavity after using tegazerol maleate. |
Last Update：2024-04-10 22:29:15
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CAS: 145158-71-0
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CAS: 145158-71-0
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
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