Compound Detail

CHEMBL1516474

TEGASEROD MALEATE

💊 Approved Drug

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💊 Approved Drug

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

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL1516474
Name	TEGASEROD MALEATE
Phase	Approved
Structure Type	MOL
InChI Key	CPDDZSSEAVLMRY-FEQFWAPWSA-N
Therapeutic	✓ Yes
Parent Compound	CHEMBL76370
Active Moiety	CHEMBL76370

Known Names

HTF 919 HTF-919 NSC-760425 Tegaserod maleate Zelmac Zelnorm

25

Targets

38

Activities

3

Assay Types

0

PK Parameters

20

Publications

6

Known Names

2

Indications

1

Mechanisms

Molecular Properties

301.4

MW (Da)

2.81

ALogP

3

HBA

4

HBD

85.3

PSA (Å²)

0.27

QED

0

Ro5 Violations

7

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2002
Availability	Withdrawn
Chirality	Achiral

Routes of Administration

Oral

Flags

Withdrawn

USAN Stem	-serod
USAN Year	2002

Extended Properties

Molecular Formula	C20H27N5O5
MW	417.47
Aromatic Rings	2
Heavy Atoms	22
NP-Likeness	-0.54

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Serotonin 4 (5-HT4) receptor partial agonist	PARTIAL AGONIST	5-hydroxytryptamine receptor 4	✓	✓

Indications

Constipation Irritable Bowel Syndrome

Drug Warnings

Withdrawn

neurotoxicity

Cardiovascular ischemic events occurring in Zelnorm-treated patients included myocardial infarction, stroke, and unstable angina pectoris

Country: United States; Australia; Canada Year: 2007

Withdrawn

cardiotoxicity

Risk for heart attack, stroke, and unstable angina

Country: United States; Australia; Canada Year: 2007

Withdrawn

cardiotoxicity

Risk for heart attack, stroke, and unstable angina

Country: United States; Australia; Canada Year: 2007

Withdrawn

cardiotoxicity

Cardiovascular ischemic events occurring in Zelnorm-treated patients included myocardial infarction, stroke, and unstable angina pectoris

Country: United States; Australia; Canada Year: 2007

Withdrawn

neurotoxicity

Risk for heart attack, stroke, and unstable angina

Country: United States; Australia; Canada Year: 2007

Withdrawn

cardiotoxicity

Cardiovascular ischemic events occurring in Zelnorm-treated patients included myocardial infarction, stroke, and unstable angina pectoris

Country: United States; Australia; Canada Year: 2007

Withdrawn

cardiotoxicity

Risk for heart attack, stroke, and unstable angina

Country: United States; Australia; Canada Year: 2007

Withdrawn

cardiotoxicity

Cardiovascular ischemic events occurring in Zelnorm-treated patients included myocardial infarction, stroke, and unstable angina pectoris

Country: United States; Australia; Canada Year: 2007

Activity Summary

Ki 21 meas. best 7.81

IC50 9 meas. best 5.09

EC50 8 meas. best 5.8

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	7.81	7.81	15.6	1
5-hydroxytryptamine receptor 1D CHEMBL1983	Ki	7.3	7.3	50.1	1
Sigma intracellular receptor 2 CHEMBL4105907	Ki	7.24	7.24	57.2	1
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	7.08	7.08	83.9	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.85	6.85	141.5	1
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	6.75	6.75	177.2	1
D(4) dopamine receptor CHEMBL219	Ki	6.72	6.72	190.6	1
5-hydroxytryptamine receptor 5A CHEMBL3426	Ki	6.7	6.7	200.9	1
D(2) dopamine receptor CHEMBL217	Ki	6.53	6.53	297.0	1
D(3) dopamine receptor CHEMBL234	Ki	6.37	6.37	426.5	1
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	6.37	6.37	431.4	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	6.25	6.25	565.9	1
Unchecked CHEMBL612545	EC50	5.8	5.44	1580.0	4
Alpha-1A adrenergic receptor CHEMBL229	Ki	5.79	5.79	1632.3	1
Alpha-1D adrenergic receptor CHEMBL223	Ki	5.79	5.79	1638.9	1
Alpha-1B adrenergic receptor CHEMBL232	Ki	5.58	5.58	2613.4	1
Mu-type opioid receptor CHEMBL233	Ki	5.55	5.55	2846.4	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	5.55	5.55	2836.6	1
BJ CHEMBL614358	EC50	5.41	5.3125	3920.0	4
Beta-1 adrenergic receptor CHEMBL213	Ki	5.4	5.4	3990.2	1
D(1B) dopamine receptor CHEMBL1850	Ki	5.38	5.38	4124.8	1
Beta-3 adrenergic receptor CHEMBL246	Ki	5.31	5.31	4936.3	1
5-hydroxytryptamine receptor 3A CHEMBL1899	Ki	5.23	5.23	5843.9	1
Ubiquitin-conjugating enzyme E2 N CHEMBL6089	IC50	5.09	4.995	8199.0	2
C-C chemokine receptor type 6 CHEMBL4423	IC50	4.63	4.63	23400.0	1
Unchecked CHEMBL612545	IC50	4.57	4.425	26930.0	6

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
5-hydroxytryptamine receptor 2B	Ki	=	15.62	nM	7.81	PDSP Secondary Binding target: HTR2B - Compounds are tested at 10 uM concentrati...	-
5-hydroxytryptamine receptor 1D	Ki	=	50.13	nM	7.3	PDSP Secondary Binding target: HTR1D - Compounds are tested at 10 uM concentrati...	-
Sigma intracellular receptor 2	Ki	=	57.24	nM	7.24	PDSP Secondary Binding target: TMEM97 - Compounds are tested at 10 uM concentrat...	-
5-hydroxytryptamine receptor 1A	Ki	=	83.91	nM	7.08	PDSP Secondary Binding target: HTR1A - Compounds are tested at 10 uM concentrati...	-
5-hydroxytryptamine receptor 2C	Ki	=	141.51	nM	6.85	PDSP Secondary Binding target: HTR2C - Compounds are tested at 10 uM concentrati...	-
Sigma non-opioid intracellular receptor 1	Ki	=	177.15	nM	6.75	PDSP Secondary Binding target: SIGMAR1 - Compounds are tested at 10 uM concentra...	-
D(4) dopamine receptor	Ki	=	190.63	nM	6.72	PDSP Secondary Binding target: DRD4 - Compounds are tested at 10 uM concentratio...	-
5-hydroxytryptamine receptor 5A	Ki	=	200.91	nM	6.7	PDSP Secondary Binding target: HTR5A - Compounds are tested at 10 uM concentrati...	-
D(2) dopamine receptor	Ki	=	296.96	nM	6.53	PDSP Secondary Binding target: DRD2 - Compounds are tested at 10 uM concentratio...	-
5-hydroxytryptamine receptor 2A	Ki	=	431.42	nM	6.37	PDSP Secondary Binding target: HTR2A - Compounds are tested at 10 uM concentrati...	-
D(3) dopamine receptor	Ki	=	426.48	nM	6.37	PDSP Secondary Binding target: DRD3 - Compounds are tested at 10 uM concentratio...	-
5-hydroxytryptamine receptor 6	Ki	=	565.85	nM	6.25	PDSP Secondary Binding target: HTR6 - Compounds are tested at 10 uM concentratio...	-
Unchecked	EC50	=	1580.0	nM	5.8	PUBCHEM_BIOASSAY: A cytotoxicity screen of small molecule inhibitors of the PhoP...	-
Alpha-1D adrenergic receptor	Ki	=	1638.89	nM	5.79	PDSP Secondary Binding target: ADRA1D - Compounds are tested at 10 uM concentrat...	-
Alpha-1A adrenergic receptor	Ki	=	1632.3	nM	5.79	PDSP Secondary Binding target: ADRA1A - Compounds are tested at 10 uM concentrat...	-
Unchecked	EC50	=	2570.0	nM	5.59	PUBCHEM_BIOASSAY: A cytotoxicity screen of small molecule inhibitors of the PhoP...	-
Alpha-1B adrenergic receptor	Ki	=	2613.36	nM	5.58	PDSP Secondary Binding target: ADRA1B - Compounds are tested at 10 uM concentrat...	-
Mu-type opioid receptor	Ki	=	2846.43	nM	5.55	PDSP Secondary Binding target: OPRM1 - Compounds are tested at 10 uM concentrati...	-
Alpha-2B adrenergic receptor	Ki	=	2836.61	nM	5.55	PDSP Secondary Binding target: ADRA2B - Compounds are tested at 10 uM concentrat...	-
BJ	EC50	=	3938.0	nM	5.41	PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Response HTS to Identify Compound...	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL4689842	HEK-293T	345
-	10.6019/CHEMBL4689842	Fibroblast	344
-	10.6019/CHEMBL4689842	U2OS	344
-	10.5281/zenodo.13943903	ADMET	79
-	10.6019/CHEMBL5209801	Sphingosine 1-phosphate receptor 1	2
-	10.6019/CHEMBL5209801	Free fatty acid receptor 4	2
-	10.6019/CHEMBL4808148	Histone deacetylase 6	2
-	10.6019/CHEMBL5209801	G-protein coupled receptor 35	2
-	10.6019/CHEMBL5209801	N-formyl peptide receptor 2	2
-	10.6019/CHEMBL5209801	Adhesion G-protein coupled receptor F1	2
-	10.6019/CHEMBL5209801	Glucose-dependent insulinotropic receptor	2
-	10.6019/CHEMBL5209801	Alpha-2A adrenergic receptor	2
-	10.6019/CHEMBL4495565	SARS-CoV-2	2
-	10.6019/CHEMBL5209801	CX3C chemokine receptor 1	2
-	10.6019/CHEMBL5209801	Type-1 angiotensin II receptor	2
-	10.6019/CHEMBL5209801	C5a anaphylatoxin chemotactic receptor 1	2
-	10.6019/CHEMBL5209801	Beta-2 adrenergic receptor	2
-	10.6019/CHEMBL5209801	Glucagon-like peptide 1 receptor	2
-	10.6019/CHEMBL5209801	Apelin receptor	2
-	10.6019/CHEMBL4513141	Escherichia coli	1

Data from ChEMBL 36 via Core Engine