 Home > Encyclopedia > Tegaserod maleate

Tegaserod maleate

Tegaserod maleate structure

CAS No:
189188-57-6
Formula:
C20H27N5O5
Chemical Name:
Tegaserod maleate
Synonyms:
SDZ-HTF-919;TEGASEROD MALEATE;ZELMAC;2-[(5-METHOXY-1H-INDOL-3-YL)METHYLENE]-N-PENTYLHYDRAZINECARBOXIMIDAMIDE, MALEATE;2-[(5-methoxy-1h-indole-3-yl)methylene]-n-pentylcarbazimidamide hydrogen maleate;TegaserodMalate;TegastrodMaleate;SDZ-HTF-919, Zelmac, 2-[(5-Methoxy-1H-indol-3-yl)methylene]-N-pentylhydrazinecarboximidamide, Maleate
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

The serotonin type 4 (5-HT4) receptor agonists are potent prokinetic agents that act on serotonin receptors in the intestine and promote intestinal peristalsis, increase gastric emptying and decrease esophageal reflux. Two 5-HT4 receptor agonists have been developed and were approved for use in the United States, but both were found to have significant serious adverse effects and have been withdrawn (cisapride) or placed under restricted use (tegaserod). Both cisapride and tegaserod have been associated with a low rate of transient serum enzyme elevations during therapy, but neither has been implicated convincing in cases of clinically apparent liver injury with jaundice.

Tegaserod maleate was launched as a new oral treatment of constipationpredominant or diarrhea-predominant irritable bowel syndrome. It can be prepared by condensation of the 5-methoxy-3-formylindole with the appropriate aminoguanidine. Tegaserod is a selective partial agonist of the excitatory 5-HT4receptor (K1= 18 nM in human caudate membranes) and was designed from the endogenous full agonist, seretonin. In the model of potentiation of the electrically stimulated contraction of longitudinal muscle of guinea pig ileum, Tegaserod exhibited a low-efficacy agonistic activity compared with serotonin. However, it appeared more potent in several studies on intestinal mucosal tissue from various species including man. A lack of effect on the QTc interval was shown in rabbits then confirmed during clinical studies. Tegaserod is also clinically developed for the treatment of other functional GI disorders such as functional dyspepsia and gastroesophageal reflux disease (GERD).

White Powder

Tegaserod maleate Basic Attributes

Molecular Weight：

417.46

Exact Mass：

417.20121898

EC Number：

630-469-2

DSSTox ID：

DTXSID6045955

Color/Form：

white to beige

ATC Code：

A03AE02

Characteristics

Melting Point：

180-183°C

Critical Temperature & Pressure：

2-8°C

Safety Information

Storage features：

+4°C

GHS Classification：

|Warning|H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P273, P280, P302+P352, P321, P333+P313, P363, P391, and P501|Aggregated GHS information provided by 2 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Hepatotoxicity：

Both cisapride and tegaserod were linked to occasional instances of serum enzyme elevations during therapy (1% to 9%), but these elevations were generally mild and asymptomatic, resolving rapidly with or without discontinuing drug. While moderate serum enzyme elevations during 5-HT4 receptor agonist therapy have been described, there have been have been no convincing reports of clinically apparent acute liver injury with jaundice attributed to these agents. Plucalopride has not been linked to increased rates of serum enzyme elevations nor to instances of acute liver injury with jaundice, but experience with its long-term use has been limited.

Drug Information

Drug Indication：

Zelnorm is indicated for the repeated symptomatic short-term treatment of women with Irritable Bowel Syndrome (IBS) whose predominant bowel habit is constipation, associated with abdominal pain/discomfort or bloating (see section 4.2).

LiverTox Summary：

MeSH：

Endogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS. (See all compounds classified as Serotonin Receptor Agonists.)

MeSH Entry Terms：

5-methoxyindol-3-carboxaldehyde amino(pentylamino)methylenehydrazone hydrogen maleate

Tegaserod maleate Use and Manufacturing

Uses

Tegaserod maleate has been used to study its cytotoxic effects on human astrocytes and to study its effects as an anti-glioblastoma agent.

Tegaserod is a gastroproeinetic used in the treatment of irritable bowel syndrome. A selective serotonin 5HT4-receptor partial agonist.

Use Classification：

Human drugs -> Zelnorm -> EMA Drug Category|Drugs for functional gastrointestinal disorders -> Human pharmacotherapeutic group|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Recommended Suppliers of Tegaserod maleate

HANGZHOU LEAP CHEM CO., LTD. Contact Supplier

CN
5 YRS

Business licensed

Trader Supplier of Intermediates,Building blocks,API,Silicones,Peptides,Lab chemicals,Biochemicals,Pharmaceuticals,Screening Compounds,Food Additives

Tegaserod maleate

CAS No.: 189188-57-6

Content: 99.00%

Inquiry