ChEMBL logo

ChEMBL

spacer
ChEMBL Statistics
  Loading Statistics...
spacer

Compound Report Card

Compound Name and Classification

Compound ID CHEMBL76370
CHEMBL76370
Compound Name TEGASEROD
ChEMBL Synonyms TEGASEROD MALEATE | ZELNORM | SDZ-HTF-919 | TEGASEROD | ZELMAC | HTF 919
Max Phase 4 (Approved)
Withdrawn Yes
Trade Names ZELMAC | ZELNORM
Molecular Formula C16H23N5O

Additional synonyms for CHEMBL76370 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CCCCCNC(=N)N\N=C\c1c[nH]c2ccc(OC)cc12
Standard InChI InChI=1S/C16H23N5O/c1-3-4-5-8-18-16(17)21-20-11-12-10-19-15- ...
Download InChI
Standard InChI Key IKBKZGMPCYNSLU-RGVLZGJSSA-N

Sources

  • British National Formulary
  • GSK Malaria Screening
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • St Jude Leishmania Screening
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification
  • Withdrawn Drugs

Alternate Forms of Compound in ChEMBL


CHEMBL76370

Molecule Features

CHEMBL76370 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Unknown

Withdrawal Information

Year 2007
Country United States
Reason Risk for heart attack, stroke, and unstable angina
Class Cardiotoxicity; Neurotoxicity

Mechanism of Action

Mechanism of Action ChEMBL Target References
Serotonin 4 (5-HT4) receptor partial agonist Serotonin 4 (5-HT4) receptor FDA

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
ConstipationD003248HP:0002019constipation3ClinicalTrials
Gastroesophageal RefluxD005764EFO:0003948gastroesophageal reflux disease3ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma2ClinicalTrials

Clinical Data

ClinicalTrials.gov TEGASEROD
The Cochrane Collaboration TEGASEROD

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL76370. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.985
CHEMBL1946 Melatonin receptor 1B Homo sapiens 0.982
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.981
CHEMBL3356 Cytochrome P450 1A2 Homo sapiens 0.937
CHEMBL2439 Myeloperoxidase Homo sapiens 0.927
CHEMBL1945 Melatonin receptor 1A Homo sapiens 0.855
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.827
CHEMBL3622 Cytochrome P450 2C19 Homo sapiens 0.787
CHEMBL1293226 Lysine-specific demethylase 4D-like Homo sapiens 0.752
CHEMBL3959 Quinone reductase 2 Homo sapiens 0.742
CHEMBL5514 Huntingtin Homo sapiens 0.368
CHEMBL1951 Monoamine oxidase A Homo sapiens 0.347
CHEMBL3563 Cruzipain Trypanosoma cruzi 0.302
CHEMBL1075322 G-protein coupled receptor 55 Homo sapiens 0.260
CHEMBL3397 Cytochrome P450 2C9 Homo sapiens 0.258
CHEMBL3459 Serotonin 1b (5-HT1b) receptor Rattus norvegicus 0.227



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2439 Myeloperoxidase Homo sapiens 0.995
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.995
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.994
CHEMBL2635 Dual specificity protein phosphatase 3 Homo sapiens 0.970
CHEMBL5508 Dual specificity tyrosine-phosphorylation-regulated kinase 1A Rattus norvegicus 0.912
CHEMBL4361 Induced myeloid leukemia cell differentiation protein Mcl-1 Homo sapiens 0.903
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.847
CHEMBL3201 Aryl hydrocarbon receptor Homo sapiens 0.813
CHEMBL1293226 Lysine-specific demethylase 4D-like Homo sapiens 0.807
CHEMBL4187 Sodium channel protein type II alpha subunit Homo sapiens 0.780
CHEMBL1293277 Niemann-Pick C1 protein Homo sapiens 0.658
CHEMBL1946 Melatonin receptor 1B Homo sapiens 0.638
CHEMBL1293299 Histone-lysine N-methyltransferase MLL Homo sapiens 0.634
CHEMBL2608 Lysosomal alpha-glucosidase Homo sapiens 0.633
CHEMBL3622 Cytochrome P450 2C19 Homo sapiens 0.622
CHEMBL5514 Huntingtin Homo sapiens 0.571
CHEMBL3959 Quinone reductase 2 Homo sapiens 0.538
CHEMBL4506 NAD-dependent deacetylase sirtuin 1 Homo sapiens 0.527
CHEMBL1741179 Probable DNA dC->dU-editing enzyme APOBEC-3A Homo sapiens 0.511
CHEMBL3356 Cytochrome P450 1A2 Homo sapiens 0.473

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
301.4 301.1903 2.81 7 85.29 BASE


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 4 0 6 4 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 9.65 3.22 2.72 2 22 0.27

Structural Alerts

There are 8 structural alerts for CHEMBL76370. To view alerts please click here.

Compound Cross References

ATC A - ALIMENTARY TRACT AND METABOLISM
A06 - DRUGS FOR CONSTIPATION
A06A - DRUGS FOR CONSTIPATION
A06AX - Other drugs for constipation
A06AX06 - tegaserod

ChemSpider ChemSpider:IKBKZGMPCYNSLU-RGVLZGJSSA-N
PubChem SID: 144205034 SID: 170466887 SID: 26749090
Wikipedia Tegaserod

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL76370



ACToR 145158-71-0
BindingDB 79022
ChEBI 51043
DrugBank DB01079
eMolecules 902539
EPA CompTox Dashboard DTXSID6045955
FDA SRS 458VC51857
IBM Patent System 850993CA4495CDB251B408F517021E57
LINCS LSM-5375
Nikkaji J822.287H
PubChem: Thomson Pharma 14776171
SureChEMBL SCHEMBL16464
ZINC ZINC000001545565

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/IKBKZGMPCYNSLU-RGVLZGJSSA-N spacer
spacer