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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
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
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ZELNORM

Approved Use

Zelnorm® (tegaserod maleate) is indicated for the short-term treatment of women with irritable bowel syndrome (IBS) whose primary bowel symptom is constipation. The safety and effectiveness of Zelnorm in men with IBS with constipation have not been established. Zelnorm® (tegaserod maleate) is indicated for the treatment of patients less than 65 years of age with chronic idiopathic constipation. The effectiveness of Zelnorm in patients 65 years or older with chronic idiopathic constipation has not been established (see Geriatric Use). The efficacy of Zelnorm for the treatment of IBS with constipation or chronic idiopathic constipation has not been studied beyond 12 weeks.

Launch Date

1.02479043E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.9 ng/mL
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TEGASEROD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
10.5 ng × h/mL
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TEGASEROD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.35 h
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TEGASEROD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
6 mg single, oral
dose: 6 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
TEGASEROD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
6 mg 2 times / day steady, oral
Recommended
Dose: 6 mg, 2 times / day
Route: oral
Route: steady
Dose: 6 mg, 2 times / day
Sources: Page: 4
unhealthy, <65 years
n = 1184
Health Status: unhealthy
Condition: IBS-C
Age Group: <65 years
Sex: F
Population Size: 1184
Sources: Page: 4
Disc. AE: Diarrhea...
AEs leading to
discontinuation/dose reduction:
Diarrhea (1.6%)
Sources: Page: 4
6 mg 2 times / day steady, oral
Recommended
Dose: 6 mg, 2 times / day
Route: oral
Route: steady
Dose: 6 mg, 2 times / day
Sources: Page: 609
unhealthy, adult
n = 881
Health Status: unhealthy
Condition: chronic constipation/ idiopathic constipation
Age Group: adult
Sex: unknown
Population Size: 881
Sources: Page: 609
Disc. AE: Diarrhea...
AEs leading to
discontinuation/dose reduction:
Diarrhea (5.7%)
Sources: Page: 609
2 mg 2 times / day steady, oral
Studied dose
Dose: 2 mg, 2 times / day
Route: oral
Route: steady
Dose: 2 mg, 2 times / day
Sources: Page: 609
unhealthy, adult
n = 861
Health Status: unhealthy
Condition: chronic constipation/ idiopathic constipation
Age Group: adult
Sex: unknown
Population Size: 861
Sources: Page: 609
Disc. AE: Diarrhea...
AEs leading to
discontinuation/dose reduction:
Diarrhea (3.3%)
Sources: Page: 609
AEs

AEs

AESignificanceDosePopulation
Diarrhea 1.6%
Disc. AE
6 mg 2 times / day steady, oral
Recommended
Dose: 6 mg, 2 times / day
Route: oral
Route: steady
Dose: 6 mg, 2 times / day
Sources: Page: 4
unhealthy, <65 years
n = 1184
Health Status: unhealthy
Condition: IBS-C
Age Group: <65 years
Sex: F
Population Size: 1184
Sources: Page: 4
Diarrhea 5.7%
Disc. AE
6 mg 2 times / day steady, oral
Recommended
Dose: 6 mg, 2 times / day
Route: oral
Route: steady
Dose: 6 mg, 2 times / day
Sources: Page: 609
unhealthy, adult
n = 881
Health Status: unhealthy
Condition: chronic constipation/ idiopathic constipation
Age Group: adult
Sex: unknown
Population Size: 881
Sources: Page: 609
Diarrhea 3.3%
Disc. AE
2 mg 2 times / day steady, oral
Studied dose
Dose: 2 mg, 2 times / day
Route: oral
Route: steady
Dose: 2 mg, 2 times / day
Sources: Page: 609
unhealthy, adult
n = 861
Health Status: unhealthy
Condition: chronic constipation/ idiopathic constipation
Age Group: adult
Sex: unknown
Population Size: 861
Sources: Page: 609
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
inconclusive
no (co-administration study)
Comment: administration with theophylline did not affect PK of theophylline
Page: 17,18
inconclusive
no (co-administration study)
Comment: administration with dextromethorphan did not affect PK of dextromethorphan
Page: 17,18
likely
likely
likely
limited
no
no
no
no
no
no
no
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
yes
yes
Tox targets

Tox targets

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

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
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 Wed Jul 05 23:57:05 UTC 2023
Edited
by admin
on Wed Jul 05 23:57:05 UTC 2023
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
Tegaserod maleate [WHO-DD]
Common Name English
3-(5-Methoxy-1H-indol-3-ylmethylene)-N-pentylcarbazimidamide hydrogen maleate
Systematic Name English
TEGASEROD MALEATE [ORANGE BOOK]
Common Name English
NSC-760425
Code 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 [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 Wed Jul 05 23:57:05 UTC 2023 , Edited by admin on Wed Jul 05 23:57:05 UTC 2023
Code System Code Type Description
FDA UNII
E5XNT3RF5A
Created by admin on Wed Jul 05 23:57:05 UTC 2023 , Edited by admin on Wed Jul 05 23:57:05 UTC 2023
PRIMARY
RXCUI
339270
Created by admin on Wed Jul 05 23:57:05 UTC 2023 , Edited by admin on Wed Jul 05 23:57:05 UTC 2023
PRIMARY RxNorm
NSC
760425
Created by admin on Wed Jul 05 23:57:05 UTC 2023 , Edited by admin on Wed Jul 05 23:57:05 UTC 2023
PRIMARY
EVMPD
SUB16463MIG
Created by admin on Wed Jul 05 23:57:05 UTC 2023 , Edited by admin on Wed Jul 05 23:57:05 UTC 2023
PRIMARY
DAILYMED
E5XNT3RF5A
Created by admin on Wed Jul 05 23:57:05 UTC 2023 , Edited by admin on Wed Jul 05 23:57:05 UTC 2023
PRIMARY
CAS
189188-57-6
Created by admin on Wed Jul 05 23:57:05 UTC 2023 , Edited by admin on Wed Jul 05 23:57:05 UTC 2023
PRIMARY
CHEBI
51044
Created by admin on Wed Jul 05 23:57:05 UTC 2023 , Edited by admin on Wed Jul 05 23:57:05 UTC 2023
PRIMARY
PUBCHEM
135413539
Created by admin on Wed Jul 05 23:57:05 UTC 2023 , Edited by admin on Wed Jul 05 23:57:05 UTC 2023
PRIMARY
CAS
1052274-43-7
Created by admin on Wed Jul 05 23:57:05 UTC 2023 , Edited by admin on Wed Jul 05 23:57:05 UTC 2023
ALTERNATIVE
ChEMBL
CHEMBL76370
Created by admin on Wed Jul 05 23:57:05 UTC 2023 , Edited by admin on Wed Jul 05 23:57:05 UTC 2023
PRIMARY
MERCK INDEX
M10523
Created by admin on Wed Jul 05 23:57:05 UTC 2023 , Edited by admin on Wed Jul 05 23:57:05 UTC 2023
PRIMARY Merck Index
USAN
NN-78
Created by admin on Wed Jul 05 23:57:05 UTC 2023 , Edited by admin on Wed Jul 05 23:57:05 UTC 2023
PRIMARY
NCI_THESAURUS
C76961
Created by admin on Wed Jul 05 23:57:05 UTC 2023 , Edited by admin on Wed Jul 05 23:57:05 UTC 2023
PRIMARY
EPA CompTox
DTXSID50904761
Created by admin on Wed Jul 05 23:57:05 UTC 2023 , Edited by admin on Wed Jul 05 23:57:05 UTC 2023
PRIMARY
SMS_ID
100000078569
Created by admin on Wed Jul 05 23:57:05 UTC 2023 , Edited by admin on Wed Jul 05 23:57:05 UTC 2023
PRIMARY
DRUG BANK
DBSALT001797
Created by admin on Wed Jul 05 23:57:05 UTC 2023 , Edited by admin on Wed Jul 05 23:57:05 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY