Active Ingredient History

  • 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

  • SMILES: CN1C[C@@H](C=C2[C@H]1Cc3c[nH]c4cccc2c34)C(=O)N[C@]5(C)O[C@@]6(O)[C@@H]7CCCN7C(=O)[C@H](Cc8ccccc8)N6C5=O.CN9C[C@@H](C=C%10[C@H]9Cc%11c[nH]c%12cccc%10c%11%12)C(=O)N[C@]%13(C)O[C@@]%14(O)[C@@H]%15CCCN%15C(=O)[C@H](Cc%16ccccc%16)N%14C%13=O.OC(C(O)C(=O)O)C(=O)O
  • Mol. Mass: 1313.43
  • ALogP: 1.99
  • ChEMBL Molecules:
More Chemistry

Combination drugs

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


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