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Details

Stereochemistry ACHIRAL
Molecular Formula C16H23N5O.C4H4O4
Molecular Weight 417.4589
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of TEGASEROD MALEATE

SMILES

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

InChI

InChIKey=CPDDZSSEAVLMRY-FEQFWAPWSA-N
InChI=1S/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-

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C16H23N5O
Molecular Weight 301.3867
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Tegaserod (3‐(5‐methoxy‐1H‐indol‐3ylmethylene)‐N‐pentyl‐carbazimidamide), an aminoguanidine indole derivative of serotonin, is a selective partial agonist highly selective for 5‐HT4 receptor with an affinity constant in the nanomolar range. Tegaserod, by acting as an agonist at neuronal 5-HT4 receptors, triggers the release of further neurotransmitters such as calcitonin gene-related peptide from sensory neurons. The activation of 5-HT4 receptors in the gastrointestinal tract stimulates the peristaltic reflex and intestinal secretion, as well as inhibits visceral sensitivity. In vivo studies showed that tegaserod enhanced basal motor activity and normalized impaired motility throughout the gastrointestinal tract. Zelnorm® (tegaserod maleate) is indicated for the short-term treatment of women with irritable bowel syndrome (IBS) whose primary bowel symptom is constipation. In addition Zelnorm® is indicated for the treatment of patients less than 65 years of age with chronic idiopathic constipation.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.0 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZELNORM

Cmax

ValueDoseCo-administeredAnalytePopulation
2.9 ng/mL
6 mg single, oral
TEGASEROD plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
10.5 ng × h/mL
6 mg single, oral
TEGASEROD plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
6.35 h
6 mg single, oral
TEGASEROD plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
6 mg single, oral
TEGASEROD plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
IBS with Constipation: The recommended dosage of Zelnorm® (tegaserod maleate) is 6 mg taken twice daily orally before meals for 4 to 6 weeks. For those women who respond to therapy at 4-6 weeks, an additional 4-6 week course can be considered. Chronic Idiopathic Constipation: The recommended dosage of Zelnorm is 6 mg taken twice daily orally before meals. Physicians and patients should periodically assess the need for continued therapy.
Route of Administration: Oral
In Vitro Use Guide
Exposure of rat colonic mucosa to tegaserod in the range of 5 nM to 5 muM for 5 or 10 min caused rapid time- and concentration-dependent desensitization of the peristaltic reflex induced by mucosal stroking. Samples of whole blood-citrate mixtures were incubated with different tegaserod concentrations mimicking human Cmax values (10 nM), 3.3 times, and 10 times Cmax for at least 1 hour.
Substance Class Chemical
Record UNII
E5XNT3RF5A
Record Status Validated (UNII)
Record Version