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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL76370
CHEMBL76370
Compound Name TEGASEROD
ChEMBL Synonyms ZELMAC | SDZ-HTF-919 | TEGASEROD | ZELNORM | HTF 919 | TEGASEROD MALEATE
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Withdrawn Yes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  • Withdrawn Drugs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First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Withdrawn

Withdrawal Information

Year 2007
Country United States
Reason Risk for heart attack, stroke, and unstable angina

Mechanism of Action

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

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
CHEMBL1945 Melatonin receptor 1A Homo sapiens 0.998
CHEMBL1946 Melatonin receptor 1B Homo sapiens 0.976
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.972
CHEMBL1941 Histamine H2 receptor Homo sapiens 0.943
CHEMBL3356 Cytochrome P450 1A2 Homo sapiens 0.937
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.937
CHEMBL1951 Monoamine oxidase A Homo sapiens 0.916
CHEMBL1983 Serotonin 1d (5-HT1d) receptor Homo sapiens 0.869
CHEMBL3622 Cytochrome P450 2C19 Homo sapiens 0.781
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.750
CHEMBL2850 Glycogen synthase kinase-3 alpha Homo sapiens 0.693
CHEMBL1293226 Lysine-specific demethylase 4D-like Homo sapiens 0.569
CHEMBL2439 Myeloperoxidase Homo sapiens 0.401
CHEMBL3397 Cytochrome P450 2C9 Homo sapiens 0.287
CHEMBL1075322 G-protein coupled receptor 55 Homo sapiens 0.264
CHEMBL2292 Dual-specificity tyrosine-phosphorylation regulated kinase 1A Homo sapiens 0.248
CHEMBL3959 Quinone reductase 2 Homo sapiens 0.204



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL1293231 Nuclear receptor ROR-gamma Mus musculus 0.990
CHEMBL1293224 Microtubule-associated protein tau Homo sapiens 0.989
CHEMBL1951 Monoamine oxidase A Homo sapiens 0.980
CHEMBL4361 Induced myeloid leukemia cell differentiation protein Mcl-1 Homo sapiens 0.912
CHEMBL2635 Dual specificity protein phosphatase 3 Homo sapiens 0.912
CHEMBL1945 Melatonin receptor 1A Homo sapiens 0.906
CHEMBL5508 Dual specificity tyrosine-phosphorylation-regulated kinase 1A Rattus norvegicus 0.869
CHEMBL1075138 Tyrosyl-DNA phosphodiesterase 1 Homo sapiens 0.761
CHEMBL1293226 Lysine-specific demethylase 4D-like Homo sapiens 0.719
CHEMBL1946 Melatonin receptor 1B Homo sapiens 0.683
CHEMBL1983 Serotonin 1d (5-HT1d) receptor Homo sapiens 0.595
CHEMBL2850 Glycogen synthase kinase-3 alpha Homo sapiens 0.541
CHEMBL1293277 Niemann-Pick C1 protein Homo sapiens 0.522
CHEMBL3318 Tyrosinase Agaricus bisporus 0.477
CHEMBL2608 Lysosomal alpha-glucosidase Homo sapiens 0.468
CHEMBL2882 Histamine H2 receptor Cavia porcellus 0.467
CHEMBL1293299 Histone-lysine N-methyltransferase MLL Homo sapiens 0.409
CHEMBL3622 Cytochrome P450 2C19 Homo sapiens 0.396
CHEMBL5514 Huntingtin Homo sapiens 0.373
CHEMBL3356 Cytochrome P450 1A2 Homo sapiens 0.361

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
301.4 301.1903 3.13 9 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 0.25

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
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