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ChEMBL Statistics
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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL442
CHEMBL442
Compound Name ERGOTAMINE
ChEMBL Synonyms LINGRAINE | Ergotamine Tartrate | ERGOSTAT | MEDIHALER ERGOTAMINE | FEMERGIN | MIGRIL | ERGOMAR | ERGOTAMINE | ERGOTAMINE TARTRATE | WIGRETTES | GYNERGEN | CAFERGOT
Max Phase 4 (Approved)
Trade Names MEDIHALER ERGOTAMINE | LINGRAINE | FEMERGIN | MIGRIL | ERGOMAR | CAFERGOT | ERGOSTAT | WIGRETTES | GYNERGEN
Molecular Formula C33H35N5O5

Additional synonyms for CHEMBL442 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES CN1C[C@@H](C=C2[C@H]1Cc3c[nH]c4cccc2c34)C(=O)N[C@]5(C)O[C@@] ...
Download SMILES
Standard InChI InChI=1S/C33H35N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28 ...
Download InChI
Standard InChI Key XCGSFFUVFURLIX-VFGNJEKYSA-N

Sources

  • British National Formulary
  • DrugMatrix
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL442

Molecule Features

CHEMBL442 compound icon
Drug Type:Natural Product-derived Rule of Five:N First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:Y Black Box:Y Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Adrenergic receptor alpha agonist Adrenergic receptor alpha DailyMed ISBN PubMed
Serotonin 1d (5-HT1d) receptor agonist Serotonin 1d (5-HT1d) receptor DailyMed ISBN PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Hypotension, OrthostaticD007024EFO:0005252orthostatic hypotension1ClinicalTrials
Migraine DisordersD008881EFO:0003821migraine disorder4ATC
ATC
ATC

Clinical Data

ClinicalTrials.gov ERGOTAMINE
The Cochrane Collaboration ERGOTAMINE

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
581.7 581.2638 1.99 4 118.21 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
6 3 1 10 3 1


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
9.62 6.94 7.37 7.24 3 43 0.43

Structural Alerts

There are no structural alerts for CHEMBL442

Compound Cross References

ATC N - NERVOUS SYSTEM
N02 - ANALGESICS
N02C - ANTIMIGRAINE PREPARATIONS
N02CA - Ergot alkaloids
N02CA02 - ergotamine

N - NERVOUS SYSTEM
N02 - ANALGESICS
N02C - ANTIMIGRAINE PREPARATIONS
N02CA - Ergot alkaloids
N02CA52 - ergotamine, combinations excl. psycholeptics

N - NERVOUS SYSTEM
N02 - ANALGESICS
N02C - ANTIMIGRAINE PREPARATIONS
N02CA - Ergot alkaloids
N02CA72 - ergotamine, combinations with psycholeptics

ChemSpider ChemSpider:XCGSFFUVFURLIX-VFGNJEKYSA-N
DailyMed ergotamine tartrate
Wikipedia Ergotamine

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL442



ACToR 113-15-5
BindingDB 50027065
ChEBI 64318
DrugBank DB00696
DrugCentral 1043
EPA CompTox Dashboard DTXSID9043774
FDA SRS PR834Q503T
Guide to Pharmacology 149
Human Metabolome Database HMDB0014834
IBM Patent System 531635B5C700C64FDC4B439235B1F2DD
Metabolights MTBLC64318
Nikkaji J2.889D
PDBe ERM
PharmGKB PA164747651
PubChem 8223
PubChem: Thomson Pharma 14911400
SureChEMBL SCHEMBL1483
ZINC ZINC000052955754

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