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Details

Stereochemistry ACHIRAL
Molecular Formula C16H23N5O.C4H4O4
Molecular Weight 417.4589
Optical Activity UNSPECIFIED
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
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C16H23N5O
Molecular Weight 301.3867
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
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

PubMed

PubMed

TitleDatePubMed
Structure of the human serotonin 5-HT4 receptor gene and cloning of a novel 5-HT4 splice variant.
2000 Feb
The 5-HT4 receptor agonist, tegaserod, is a potent 5-HT2B receptor antagonist in vitro and in vivo.
2004 Nov
Patents

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
Created
by admin
on Tue Oct 22 01:19:59 UTC 2019
Edited
by admin
on Tue Oct 22 01:19:59 UTC 2019
Record UNII
E5XNT3RF5A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TEGASEROD MALEATE
MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN  
Official Name English
TEGASEROD MALEATE [MI]
Common Name English
3-(5-METHOXY-1H-INDOL-3-YLMETHYLENE)-N-PENTYLCARBAZIMIDAMIDE HYDROGEN MALEATE
Systematic Name English
TEGASEROD MALEATE [ORANGE BOOK]
Common Name English
TEGASEROD MALEATE [VANDF]
Common Name English
HYDRAZINECARBOXIMIDAMIDE, 2-((5-METHOXY-1H-INDOL-3-YL)METHYLENE)-N-PENTYL-, (2E)-, (2Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
HYDRAZINECARBOXIMIDAMIDE,2-((5-METHOXY-1H-INDOL-3-YL)METHYLENE)-N-PENTYL (2Z)-2-BUTENEDIOATE(1:1)
Common Name English
HTF-919
Code English
TEGASEROD MALEATE [WHO-DD]
Common Name English
TEGASEROD MALEATE [USAN]
Common Name English
TEGASEROD MALEATE [MART.]
Common Name English
ZELNORM
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C66885
Created by admin on Tue Oct 22 01:19:59 UTC 2019 , Edited by admin on Tue Oct 22 01:19:59 UTC 2019
Code System Code Type Description
RXCUI
339270
Created by admin on Tue Oct 22 01:19:59 UTC 2019 , Edited by admin on Tue Oct 22 01:19:59 UTC 2019
PRIMARY RxNorm
EVMPD
SUB16463MIG
Created by admin on Tue Oct 22 01:19:59 UTC 2019 , Edited by admin on Tue Oct 22 01:19:59 UTC 2019
PRIMARY
CAS
189188-57-6
Created by admin on Tue Oct 22 01:19:59 UTC 2019 , Edited by admin on Tue Oct 22 01:19:59 UTC 2019
PRIMARY
CAS
1052274-43-7
Created by admin on Tue Oct 22 01:19:59 UTC 2019 , Edited by admin on Tue Oct 22 01:19:59 UTC 2019
ALTERNATIVE
ChEMBL
CHEMBL76370
Created by admin on Tue Oct 22 01:19:59 UTC 2019 , Edited by admin on Tue Oct 22 01:19:59 UTC 2019
PRIMARY
MERCK INDEX
M10523
Created by admin on Tue Oct 22 01:19:59 UTC 2019 , Edited by admin on Tue Oct 22 01:19:59 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C76961
Created by admin on Tue Oct 22 01:19:59 UTC 2019 , Edited by admin on Tue Oct 22 01:19:59 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY