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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL1065
CHEMBL1065
Compound Name METHYSERGIDE
ChEMBL Synonyms Sansert | Methysergide | METHYSERGIDE MALEATE | SANSERT
Max Phase 4 (Approved)
Trade Names SANSERT
Molecular Formula C21H27N3O2

Additional synonyms for CHEMBL1065 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CC[C@@H](CO)NC(=O)[C@H]1CN(C)[C@@H]2Cc3cn(C)c4cccc(C2=C1)c34
Standard InChI InChI=1S/C21H27N3O2/c1-4-15(12-25)22-21(26)14-8-17-16-6-5-7- ...
Download InChI
Standard InChI Key KPJZHOPZRAFDTN-ZRGWGRIASA-N

Sources

  • British National Formulary
  • DrugMatrix
  • Harvard Malaria Screening
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL1065

Molecule Features

CHEMBL1065 compound icon
Drug Type:Natural Product-derived Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Discontinued

Mechanism of Action

Mechanism of Action ChEMBL Target References
Serotonin 1a (5-HT1a) receptor partial agonist Serotonin 1a (5-HT1a) receptor ISBN PubMed
Serotonin 2b (5-HT2b) receptor antagonist Serotonin 2b (5-HT2b) receptor ISBN PubMed
Serotonin 2c (5-HT2c) receptor antagonist Serotonin 2c (5-HT2c) receptor ISBN

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
MIGRAINE DISORDERSD008881EFO:0003821MIGRAINE DISORDER4ATC

Clinical Data

ClinicalTrials.gov METHYSERGIDE
The Cochrane Collaboration METHYSERGIDE

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 CHEMBL1065. 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
CHEMBL5200 C-X-C chemokine receptor type 3 Mus musculus 1.000
CHEMBL3459 Serotonin 1b (5-HT1b) receptor Rattus norvegicus 1.000
CHEMBL3223 Serotonin 7 (5-HT7) receptor Rattus norvegicus 0.958
CHEMBL1850 Dopamine D5 receptor Homo sapiens 0.227

10uM


ChEMBL_ID Target Name Organism Score
CHEMBL5200 C-X-C chemokine receptor type 3 Mus musculus 1.000
CHEMBL3459 Serotonin 1b (5-HT1b) receptor Rattus norvegicus 0.997
CHEMBL3223 Serotonin 7 (5-HT7) receptor Rattus norvegicus 0.906
CHEMBL1942 Alpha-2b adrenergic receptor Homo sapiens 0.664

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
353.5 353.2103 2.27 4 57.5 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 2 0 5 2 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
- 7.15 1.81 1.67 2 26 0.89

Structural Alerts

There are no structural alerts for CHEMBL1065

Compound Cross References

ATC N - NERVOUS SYSTEM
N02 - ANALGESICS
N02C - ANTIMIGRAINE PREPARATIONS
N02CA - Ergot alkaloids
N02CA04 - methysergide

ChemSpider ChemSpider:KPJZHOPZRAFDTN-ZRGWGRIASA-N
PubChem SID: 144204446 SID: 170464684 SID: 26751590 SID: 90340563
Wikipedia Methysergide

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL1065



ACToR 361-37-5 156558-44-0
BindingDB 30708 50031942
ChEBI 92629
DrugCentral 1775
EPA CompTox Dashboard DTXSID2023307
FDA SRS XZA9HY6Z98
Guide to Pharmacology 134
IBM Patent System CADF9481BC752F75692909E4FB394F65
KEGG Ligand C07199
LINCS LSM-2786
Metabolights MTBLC92629
Nikkaji J76.430B
PharmGKB PA164743265
PubChem 9681
SureChEMBL SCHEMBL41843
ZINC ZINC000053151228

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