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Compound Detail

CHEMBL76370

TEGASEROD
💊 Approved Drug
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💊 Approved Drug
CCCCCNC(=N)N/N=C/c1c[nH]c2ccc(OC)cc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL76370
Name TEGASEROD
Phase Approved
Structure Type MOL
InChI Key IKBKZGMPCYNSLU-RGVLZGJSSA-N
Therapeutic ✓ Yes

Known Names

HTF 919 HTF919 SDZ-HTF-919 Tegaserod
4
Targets
18
Activities
3
Assay Types
19
PK Parameters
20
Publications
4
Known Names
3
Indications

Molecular Properties

301.4
MW (Da)
2.81
ALogP
3
HBA
4
HBD
85.3
PSA (Ų)
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Availability Withdrawn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Withdrawn Natural Product
USAN Stem -serod
USAN Year 1999

Extended Properties

Molecular Formula C16H23N5O
MW 301.39
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.54

Indications

Constipation Dyspepsia Gastroesophageal Reflux

ATC Classification

A06AX06
tegaserod
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR CONSTIPATION

Drug Warnings

Withdrawn
cardiotoxicity
Cardiovascular ischaemic events
Country: United States; Australia; Canada   Year: 2007

Activity Summary

EC50 8 meas. best 9.0
Ki 6 meas. best 8.4
IC50 4 meas. best 5.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 4
CHEMBL1875
 EC50 9.0 8.54 1.0 5
5-hydroxytryptamine receptor 4
CHEMBL1875
 Ki 8.4 8.222 4.0 5
5-hydroxytryptamine receptor 4
CHEMBL5017
 EC50 8.2 8.1 6.3 3
5-hydroxytryptamine receptor 3A
CHEMBL1899
 Ki 5.6 5.6 2511.9 1
Unchecked
CHEMBL612545
 IC50 5.5 5.0925 3131.8 4

Pharmacokinetic Data

Parameter Value Units Species
AUC 21.0 ng.hr.mL-1 Rattus norvegicus
CL 18.0 mL.min-1.kg-1 Homo sapiens
CL 17.6 mL.min-1.kg-1 Homo sapiens
CL 18.0 mL.min-1.kg-1 Homo sapiens
CL 18.0 mL.min-1.kg-1 Homo sapiens
CL 77.0 L/hr Mus musculus
Cmax 19.91 nM Rattus norvegicus
F 10.0 % Homo sapiens
F 5.0 % Rattus norvegicus
Fu 0.02 - Homo sapiens
Fu 0.02 - Homo sapiens
MRT 4.9 hr Homo sapiens
T1/2 1.5 hr Rattus norvegicus
T1/2 1.8 hr Rattus norvegicus
T1/2 11.0 hr Homo sapiens
T1/2 1.5 hr Rattus norvegicus
T1/2 90.0 hr Rattus norvegicus
T1/2 1.5 hr Rattus norvegicus
T1/2 11.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 4 EC50 = 1.0 nM 9.0 Agonist activity at human 5HT4C receptor expressed at 100 fold physiological-lev... 22683222
5-hydroxytryptamine receptor 4 EC50 = 1.995 nM 8.7 Agonist activity at human 5HT4C receptor expressed in a cell line expressing rec... 22683222
5-hydroxytryptamine receptor 4 EC50 = 2.512 nM 8.6 Agonist activity at human recombinant 5HT4c receptor expressed in HEK293 cells a... 22959244
5-hydroxytryptamine receptor 4 EC50 = 2.512 nM 8.6 Agonist activity at human recombinant 5HT4 receptor assessed as cAMP accumulatio... 23756062
5-hydroxytryptamine receptor 4 Ki = 3.981 nM 8.4 Binding affinity to human recombinant 5HT4 receptor 23756062
5-hydroxytryptamine receptor 4 Ki = 3.981 nM 8.4 Displacement of [3H]GR113808 from human recombinant 5HT4c receptor expressed in ... 22959244
5-hydroxytryptamine receptor 4 Ki = 3.981 nM 8.4 Binding affinity at 5HT4 receptor 19261477
5-hydroxytryptamine receptor 4 Ki = 3.981 nM 8.4 Displacement of [3H]GR113808 from human recombinant 5HT4C receptor expressed in ... 22683222
5-hydroxytryptamine receptor 4 EC50 = 6.31 nM 8.2 Agonist activity at 5HT4 receptor in guinea pig colon assessed as longitudinal m... 22683222
5-hydroxytryptamine receptor 4 EC50 = 6.31 nM 8.2 Agonist activity at 5HT4 receptor in guinea pig colonic longitudinal muscle/myen... 22959244
5-hydroxytryptamine receptor 4 EC50 = 12.59 nM 7.9 Induction of 5-HT4 receptor-mediated contraction in guinea pig longitudinal musc... 23756062
5-hydroxytryptamine receptor 4 EC50 = 15.85 nM 7.8 5-HT4C receptor-mediated exchange of GDP for europium labeled GTP (pEC50) 22683222
5-hydroxytryptamine receptor 4 Ki = 31.0 nM 7.51 Displacement of [N-methyl-3H]GR-113808 from human 5HT4 receptor expressed in HEK... 17067154
5-hydroxytryptamine receptor 3A Ki = 2511.89 nM 5.6 Binding affinity to human recombinant 5HT3 receptor 23756062
Unchecked IC50 = 3131.8 nM 5.5 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
Unchecked IC50 = 7174.71 nM 5.14 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture nuclear area decrease (vi... -
Unchecked IC50 = 10858.56 nM 4.96 PubChem BioAssay. GLP1 secretion from NCI-H716 cells-IC50. (Class of assay: co... -
Unchecked IC50 = 16844.2 nM 4.77 PubChem BioAssay. insulin secretion from INS-1E cells in the presence of 5 mM gl... -

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
22683222 10.1016/j.bmcl.2012.05.034 5-hydroxytryptamine receptor 4 9
20070106 10.1021/jm901371v Homo sapiens 8
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 6
22959244 10.1016/j.bmcl.2012.08.051 5-hydroxytryptamine receptor 4 5
23756062 10.1016/j.bmcl.2013.05.018 5-hydroxytryptamine receptor 4 5
19663444 10.1021/jm900881j Rattus norvegicus 5
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 4
37468498 10.1038/s41467-023-40064-9 Androgen receptor 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 4
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 4
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 4
37468498 10.1038/s41467-023-40064-9 Progesterone receptor 4
18426954 10.1124/dmd.108.020479 ADMET 4
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 3
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 3
38516587 10.1039/d3md00677h ADMET 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2A 3

Data from ChEMBL 36 via Core Engine