ergotamine Report issue

Small molecule Approved FDA
AACT ChEMBL DrugBank Drug Central Drugs@FDA KEGG MeSH PubChem repoDB

Active Ingredient History

NOW
  • Now
The isolation and naming of ergotamine by Stoll occurred in 1925 but the complete elucidation of structure was not achieved until 1951, with synthesis following some 10 years later. Current sources of ergotamine include the isolation from field ergot and fermentation broth, as well as synthesis via coupling of (+)-lysergic acid with the appropriate synthetic peptidic moiety. Ergotamine was introduced into world commerce in 1921, and is currently marketed as its water soluble tartrate salt. Ergotamine is a partial agonist at various tryptaminergic receptors (including the serotonin receptor [5-HT2]) and at various α-adrenergic receptors in blood vessels and various smooth muscles. It is likely that the major activity of ergotamine and related alkaloids is one of agonism at the 5-HT1B/1D receptors, just as with the “triptan” antimigraine compounds. FDA-labeled indications for ergotamine tartrate are in the abortion or prevention of vascular headaches, such as migraine, migraine variant, cluster headache, and histaminic cephalalgia.   NCATS

Chemistry

  • SMILES: CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](Cc4ccccc4)N3C2=O)C=C2c3cccc4[nH]cc(c34)C[C@H]21.CN1C[C@H](C(=O)N[C@]2(C)O[C@@]3(O)[C@@H]4CCCN4C(=O)[C@H](Cc4ccccc4)N3C2=O)C=C2c3cccc4[nH]cc(c34)C[C@H]21.O=C(O)C(O)C(O)C(=O)O
  • InChIKey: CJMJLDQKTOJACI-SEUSHGJOSA-N
  • Mol. Mass: 1313.43
  • ALogP: 1.99
  • ChEMBL Molecules:
    ergotamine tartrate  
    ergotamine tartrate  
    ergotamine  
More Chemistry

Pharmacology

Combination drugs

( caffeine, ergotamine - other names: migergot, wigraine )

Alternative names

12'-hydroxy-2'-methyl-5'alpha-(phenylmethyl)ergotaman-3',6',18-trione | (5'alpha)-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione | cafergot | caffeine - ergotamine | caffeine, ergotamine drug combination | ergomar | ergostat | ergotamin | ergotamina | ergotamine | ergotamine tartrate | ergotaminine | ergotaminum | femergin | gynergen | lingraine | medihaler ergotamine | migril | wigrettes

Organizations (14)

Research & Development (4)

Organization Org Type FDA approvals Clinical Trials involvement Org ID Force Sort

Marketing (10)

Organization Org Type FDA approvals Clinical Trials involvement Org ID Force Sort

Indications (5)

Approved Indications (2)


 

Headache

Migraine Disorders

Experimental Indications - Clinical Trial Phases 1-4 (5)


 

Headache (Phase 3)

Hypotension, Orthostatic (Phase 1)

Migraine Disorders (Phase 4)

Postpartum Hemorrhage (Phase 4)

Pure Autonomic Failure (Phase 1)

Overview

  • Highest Phase: Phase 4
  • # of Trials: 4
  • # of Trial Organizations: 4

Trials by Phase

Trial Phase Start Date Organizations Indications

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