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Details

Stereochemistry ACHIRAL
Molecular Formula C16H23N5O
Molecular Weight 301.3873
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of TEGASEROD

SMILES

CCCCCNC(=N)N/N=C(\[H])/c1c[nH]c2ccc(cc12)OC

InChI

InChIKey=IKBKZGMPCYNSLU-RGVLZGJSSA-N
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+

HIDE SMILES / InChI

Molecular Formula C16H23N5O
Molecular Weight 301.3873
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 Sat Jun 26 11:07:43 UTC 2021
Edited
by admin
on Sat Jun 26 11:07:43 UTC 2021
Record UNII
458VC51857
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TEGASEROD
EMA EPAR   INN   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
1-(((5-METHOXYINDOL-3-YL)METHYLENE)AMINO)-3-PENTYLGUANIDINE
Systematic Name English
HYDRAZINECARBOXIMIDAMIDE, 2-((5-METHOXY-1H-INDOL-3-YL)METHYLENE)-N-PENTYL-, (2E)-
Systematic Name English
TEGASEROD [MI]
Common Name English
SDZ-HTF-919
Code English
TEGASEROD [VANDF]
Common Name English
HYDRAZINECARBOXIMIDAMIDE, 2-((5-METHOXY-1H-INDOL-3-YL)METHYLENE)-N-PENTYL-
Systematic Name English
HTF 919
Code English
TEGASEROD [INN]
Common Name English
TEGASEROD [WHO-DD]
Common Name English
TEGASEROD [USAN]
Common Name English
TEGASEROD [EMA EPAR]
Common Name English
Classification Tree Code System Code
WHO-VATC QA06AX06
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
NDF-RT N0000175815
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
LIVERTOX 925
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
WHO-ATC A06AX06
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
NCI_THESAURUS C66885
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
NDF-RT N0000175816
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
WHO-ATC A03AE02
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
Code System Code Type Description
INN
7606
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
PRIMARY
DRUG CENTRAL
2579
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
PRIMARY
LACTMED
Tegaserod
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
PRIMARY
EVMPD
SUB04713MIG
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
PRIMARY
NCI_THESAURUS
C66583
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
PRIMARY
RXCUI
139778
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
PRIMARY RxNorm
CAS
1044642-88-7
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
ALTERNATIVE
IUPHAR
226
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
PRIMARY
ChEMBL
CHEMBL76370
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
PRIMARY
FDA UNII
458VC51857
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
PRIMARY
EPA CompTox
145158-71-0
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
PRIMARY
PUBCHEM
135409453
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
PRIMARY
MERCK INDEX
M10523
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
TEGASEROD
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
PRIMARY
DRUG BANK
DB01079
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
PRIMARY
MESH
C105050
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
PRIMARY
CAS
145158-71-0
Created by admin on Sat Jun 26 11:07:44 UTC 2021 , Edited by admin on Sat Jun 26 11:07:44 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
EXCRETED UNCHANGED
Approximately two-thirds of the orally administered dose of tegaserod is excreted unchanged in the feces, with the remaining one-third excreted in the urine, primarily as the main metabolite.
FECAL
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> INHIBITOR
Ki
METABOLIC ENZYME -> INHIBITOR
Ki
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC ORAL ADMINISTRATION

Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC