| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-05-22 05:25:40 UTC |
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| Update Date | 2016-11-09 01:15:51 UTC |
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| Accession Number | CHEM018665 |
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| Identification |
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| Common Name | Tegaserod |
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| Class | Small Molecule |
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| Description | Novartis' brand name Zelnorm (tegaserod) had originally received approval from the US FDA in 2002 for the treatment of irritable bowel syndrome with constipation (IBS-C). It was, however, voluntarily withdrawn from widespread use in the US market in 2007 after concerns arose over the possibility that tegaserod could potentially cause dangerous cardiovascular events in patients. Since then, closer evaluations of the original data suggesting such cardiovascular risk have resulted in the limited reintroduction or 're-approval' of tegaserod for treatment of IBS-C specifically in female patients less than 65 years of age and whom are considered to be at a lower risk of a cardiovascular event than the broader population. Zelnorm (tegaserod) by Sloan Pharma subsequently gained re-approval in April of 2019. Nevertheless, tegaserod remains un-approved in certain regions.
Despite the relative complications involved in its history of regulatory approval, ever since its first introduction in 2002 tegaserod remains the only therapy for IBS-C that possesses the unique mechanism of action of acting on serotonin-4 (5-HT(4)) receptors in smooth muscle cells and in the gastrointestinal wall to facilitate actions like esophageal relaxation, peristaltic gut movement, and natural secretions in the gut, among others. |
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| Contaminant Sources | - STOFF IDENT Compounds
- ToxCast & Tox21 Chemicals
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| Contaminant Type | Not Available |
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| Chemical Structure | |
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| Synonyms | | Value | Source |
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| 1-(((5-Methoxyindol-3-yl)methylene)amino)-3-pentylguanidine | ChEBI | | Tegaserodum | ChEBI | | 5-Methoxyindol-3-carboxaldehyde amino(pentylamino)methylenehydrazone hydrogen maleate | MeSH | | HTF 919 | MeSH | | SDZ HTF 919 | MeSH | | SDZ HTF-919 | MeSH | | Zelmac | MeSH | | Zelnorm | MeSH | | Tegaserod maleate | MeSH |
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| Chemical Formula | C16H23N5O |
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| Average Molecular Mass | 301.394 g/mol |
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| Monoisotopic Mass | 301.190 g/mol |
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| CAS Registry Number | 145158-71-0 |
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| IUPAC Name | N'-[(E)-[(5-methoxy-1H-indol-3-yl)methylidene]amino]-N-pentylguanidine |
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| Traditional Name | tegaserod |
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| SMILES | CCCCCNC(=N)N\N=C\C1=CNC2=C1C=C(OC)C=C2 |
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| InChI Identifier | InChI=1S/C16H23N5O/c1-3-4-5-8-18-16(17)21-20-11-12-10-19-15-7-6-13(22-2)9-14(12)15/h6-7,9-11,19H,3-5,8H2,1-2H3,(H3,17,18,21)/b20-11+ |
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| InChI Key | IKBKZGMPCYNSLU-RGVLZGJSSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. |
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| Kingdom | Organic compounds |
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| Super Class | Organoheterocyclic compounds |
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| Class | Indoles and derivatives |
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| Sub Class | Indoles |
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| Direct Parent | Indoles |
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| Alternative Parents | |
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| Substituents | - Indole
- Anisole
- Alkyl aryl ether
- Substituted pyrrole
- Benzenoid
- Pyrrole
- Heteroaromatic compound
- Guanidine
- Azacycle
- Ether
- Carboximidamide
- Hydrocarbon derivative
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Imine
- Organic nitrogen compound
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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| Biological Properties |
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| Status | Detected and Not Quantified |
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| Origin | Not Available |
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| Cellular Locations | Not Available |
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| Biofluid Locations | Not Available |
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| Tissue Locations | Not Available |
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| Pathways | Not Available |
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| Applications | Not Available |
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| Biological Roles | Not Available |
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| Chemical Roles | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Appearance | Not Available |
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| Experimental Properties | | Property | Value |
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| Melting Point | Not Available | | Boiling Point | Not Available | | Solubility | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | | Spectrum Type | Description | Splash Key | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0ukc-1914000000-ff53cb6dc16afb4aa8a7 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-3921000000-2b8456cdcc5e72cea6ec | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00di-8910000000-f6568ccd20aaffdbc5cf | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-1915000000-6caf49bb8d7f5e686c1c | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-1900000000-377e9b9802ef5e86bab3 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0076-9600000000-60f9a3d72f75242ff470 | Spectrum |
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| Toxicity Profile |
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| Route of Exposure | Not Available |
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| Mechanism of Toxicity | Not Available |
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| Metabolism | Not Available |
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| Toxicity Values | Not Available |
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| Lethal Dose | Not Available |
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| Carcinogenicity (IARC Classification) | Not Available |
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| Uses/Sources | Not Available |
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| Minimum Risk Level | Not Available |
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| Health Effects | Not Available |
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| Symptoms | Not Available |
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| Treatment | Not Available |
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| Concentrations |
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| Not Available |
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| External Links |
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| DrugBank ID | DB01079 |
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| HMDB ID | Not Available |
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| FooDB ID | Not Available |
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| Phenol Explorer ID | Not Available |
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| KNApSAcK ID | Not Available |
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| BiGG ID | Not Available |
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| BioCyc ID | Not Available |
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| METLIN ID | Not Available |
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| PDB ID | Not Available |
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| Wikipedia Link | Tegaserod |
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| Chemspider ID | Not Available |
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| ChEBI ID | 51043 |
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| PubChem Compound ID | 135409453 |
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| Kegg Compound ID | Not Available |
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| YMDB ID | Not Available |
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| ECMDB ID | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| MSDS | Not Available |
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| General References | Not Available |
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