TEGASEROD MALEATE

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 Search

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	C16H23N5O
Molecular Weight	301.3867
Charge	0
Count

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

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11207504 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021200s014lbl.pdf

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 Target	Pharmacology	Condition	Potency
Serotonin 4 (5-HT4) receptor 38 Target ID: CHEMBL1875 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/021200s014lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/23756062	Partial Agonist 297		1.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Constipation 112 Sources: https://adisinsight.springer.com/drugs/800006410 https://www.ncbi.nlm.nih.gov/pubmed/18360619	Primary		Approved 8583	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 2002

C_max

Value	Dose	Co-administered	Analyte	Population
2.9 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf	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

Value	Dose	Co-administered	Analyte	Population
10.5 ng × h/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
6.35 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
2% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf	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

Dose	Population	Adverse 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf	unhealthy, <65 years Health Status: unhealthy Age Group: <65 years Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf	Disc. AE: Diarrhea... AEs leading to discontinuation/dose reduction: Diarrhea (1.6%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf
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: https://pubmed.ncbi.nlm.nih.gov/16678076/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/16678076/	Disc. AE: Diarrhea... AEs leading to discontinuation/dose reduction: Diarrhea (5.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/16678076/
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: https://pubmed.ncbi.nlm.nih.gov/16678076/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/16678076/	Disc. AE: Diarrhea... AEs leading to discontinuation/dose reduction: Diarrhea (3.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/16678076/

AEs

AE	Significance	Dose	Population
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf	unhealthy, <65 years Health Status: unhealthy Age Group: <65 years Sex: F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf
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: https://pubmed.ncbi.nlm.nih.gov/16678076/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/16678076/
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: https://pubmed.ncbi.nlm.nih.gov/16678076/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/16678076/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 1057 CYP2C19 2057 CYP2E1 1060 CYP1A2 2153 MATE1 415 MATE2 267 BCRP 910	BCRP 697 P-gp 2052 OAT1 395 OAT3 391 OCT1 393 OCT2 434 OATP1B1 503 OATP1B3 435 MATE1 182 MATE2 98 BSEP 63	CYP2B6 669 CYP1A2 832

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-200_Zelnorm_biopharmr_P1.pdf#page=17 Page: 17,18	inconclusive	no (co-administration study) Comment: administration with theophylline did not affect PK of theophylline Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-200_Zelnorm_biopharmr_P1.pdf#page=17 Page: 17,18
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-200_Zelnorm_biopharmr_P1.pdf#page=17 Page: 17,18	inconclusive	no (co-administration study) Comment: administration with dextromethorphan did not affect PK of dextromethorphan Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-200_Zelnorm_biopharmr_P1.pdf#page=17 Page: 17,18
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf#page=12 Page: 12.0	likely
MATE1 416	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf#page=12 Page: 12.0	likely
MATE2 267	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf#page=12 Page: 12.0	likely
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf#page=12 Page: 12.0	limited
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf#page=12 Page: 12.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-200_Zelnorm_biopharmr_P1.pdf#page=17 Page: 17.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-200_Zelnorm_biopharmr_P1.pdf#page=17 Page: 17.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-200_Zelnorm_biopharmr_P1.pdf#page=17 Page: 17.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-200_Zelnorm_biopharmr_P1.pdf#page=17 Page: 17.0	no
CYP3A4 2633	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf#page=12 Page: 12.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-200_Zelnorm_biopharmr_P1.pdf#page=17 Page: 17.0	no

Drug as victim

Target	Modality	Activity
BSEP 63	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf#page=12 Page: 12.0	no
MATE1 182	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf#page=12 Page: 12.0	no
MATE2 98	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf#page=12 Page: 12.0	no
OAT1 395	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf#page=12 Page: 12.0	no
OAT3 391	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf#page=12 Page: 12.0	no
OATP1B1 503	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf#page=12 Page: 12.0	no
OATP1B3 435	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf#page=12 Page: 12.0	no
OCT1 393	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf#page=12 Page: 12.0	no
OCT2 434	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf#page=12 Page: 12.0	no
BCRP 697	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf#page=12 Page: 12.0	yes
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021200Orig1s015lbl.pdf#page=12 Page: 12.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21-200_Zelnorm_pharmr_P1.pdf#page=24 Page: 24.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:51043	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:51043
eMolecules	902539	https://www.emolecules.com/cgi-bin/more?vid=902539
ZINC	ZINC000001545565	http://zinc15.docking.org/substances/ZINC000001545565

PubMed

Title	Date	PubMed
The 5-HT4 receptor agonist, tegaserod, is a potent 5-HT2B receptor antagonist in vitro and in vivo.	2004-11	15466450
Structure of the human serotonin 5-HT4 receptor gene and cloning of a novel 5-HT4 splice variant.	2000-02	10646498

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 `Mon Mar 31 18:30:21 GMT 2025` Edited by `admin` on `Mon Mar 31 18:30:21 GMT 2025`
Record UNII	E5XNT3RF5A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TEGASEROD MALEATE [MI]

Preferred Name

English

TEGASEROD MALEATE

Official 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