Tegaserod (CED0007254)

Record Information

Version

1.0

Creation Date

2016-05-22 05:25:40 UTC

Update Date

2026-08-19 17:04:30 UTC

Accession Number

CHEM018665

Identification

Common Name

Tegaserod

Class

Small Molecule

Description

Tegaserod is an organic compound with the formula C16H23N5O and an average molecular weight of 301.39 g/mol. Tegaserod belongs to the indoles, a subclass of indoles and derivatives within the organic compounds. This compound is utilized in healthcare, pharmaceuticals, and veterinary products as a drug for constipation, with oral exposure being the recorded route. Its pharmacological activity involves four protein targets. Specifically, it acts as a partial agonist of the 5-hydroxytryptamine receptor 4 (HTR4) and functions as an antagonist/antagonist of the 5-hydroxytryptamine receptor 2B (HTR2B), 5-hydroxytryptamine receptor 2C (HTR2C), and 5-hydroxytryptamine receptor 2A (HTR2A).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
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

Chemical Formula

C₁₆H₂₃N₅O

Average Molecular Mass

301.394 g/mol

Monoisotopic Mass

301.190 g/mol

CAS Registry Number

145158-71-0

IUPAC Name

N'-[(E)-[(5-methoxy-1H-indol-3-yl)methylidene]amino]-N-pentylguanidine

Traditional Name

tegaserod

SMILES

CCCCCNC(=N)N\N=C\C1=CNC2=C1C=C(OC)C=C2

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+

InChI Key

IKBKZGMPCYNSLU-RGVLZGJSSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

Indoles

Alternative Parents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

guanidines (CHEBI:51043 )
indoles (CHEBI:51043 )
carboxamidine (CHEBI:51043 )
hydrazines (CHEBI:51043 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.029 g/L	ALOGPS
logP	2.76	ALOGPS
logP	2.95	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	15.24	ChemAxon
pKa (Strongest Basic)	8.5	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	85.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	110.25 m³·mol⁻¹	ChemAxon
Polarizability	34.96 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ukc-1914000000-ff53cb6dc16afb4aa8a7	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-3921000000-2b8456cdcc5e72cea6ec	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-8910000000-f6568ccd20aaffdbc5cf	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-1915000000-6caf49bb8d7f5e686c1c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-000i-1900000000-377e9b9802ef5e86bab3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0076-9600000000-60f9a3d72f75242ff470	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
216.0	Log mg/kg	[120:380]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
253	Drugs for constipation	Healthcare, pharmaceuticals & veterinary products	Not Available

Pathways

1 pathway

Tegaserod Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	5-hydroxytryptamine receptor 2C	P28335	Humans	Predicted (SEA)	2.02408
Click to view 3D structure	5-hydroxytryptamine receptor 1D	P28221	Humans	Predicted (SEA)	1.08989
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	10.5875
Click to view 3D structure	5-hydroxytryptamine receptor 2B	P41595	Humans	Predicted (SEA)	4.67095
Click to view 3D structure	5-hydroxytryptamine receptor 1A	P08908	Humans	Predicted (SEA)	23.6662
Click to view 3D structure	5-hydroxytryptamine receptor 3A	P46098	Humans	Predicted (SEA)	1.40129
Click to view 3D structure	5-hydroxytryptamine receptor 7	P34969	Humans	Predicted (SEA)	34.8764
Click to view 3D structure	5-hydroxytryptamine receptor 6	P50406	Humans	Predicted (SEA)	28.6485
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P14842	Rattus norvegicus	Predicted (SEA)	33.9423
Click to view 3D structure	D(2) dopamine receptor	P14416	Humans	Predicted (SEA)	126.972
Click to view 3D structure	5-hydroxytryptamine receptor 4	Q13639	Humans	Predicted (SEA)	8.48557
Click to view 3D structure	5-hydroxytryptamine receptor 5A	P47898	Humans	Predicted (SEA)	15.9591
Click to view 3D structure	D(3) dopamine receptor	P35462	Humans	Predicted (SEA)	112.181
Click to view 3D structure	D(4) dopamine receptor	P21917	Humans	Predicted (SEA)	82.5202
Click to view 3D structure	Alpha-1B adrenergic receptor	P35368	Humans	Predicted (SEA)	41.1822
Click to view 3D structure	Alpha-2B adrenergic receptor	P18089	Humans	Predicted (SEA)	31.6068
Click to view 3D structure	Alpha-1A adrenergic receptor	P35348	Humans	Predicted (SEA)	66.2497
Click to view 3D structure	Beta-1 adrenergic receptor	P08588	Humans	Predicted (SEA)	16.7376
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	115.139
Click to view 3D structure	5-hydroxytryptamine receptor 4	O70528	Cavia porcellus	Predicted (SEA)	10.1204
Click to view 3D structure	Alpha-1D adrenergic receptor	P25100	Humans	Predicted (SEA)	41.9607
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	215.954
Click to view 3D structure	D(1B) dopamine receptor	P21918	Humans	Predicted (SEA)	48.5779
Click to view 3D structure	Ubiquitin-conjugating enzyme E2 N	P61088	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	Beta-3 adrenergic receptor	P13945	Humans	Predicted (SEA)	15.0249