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Ergotamine

CHEBI:CHEBI_4562

Definition

Ergotamine in which a single bond replaces the double bond between positions 9 and 10. A semisynthetic ergot alkaloid with weaker oxytocic and vasoconstrictor properties than ergotamine, it is used (as the methanesulfonic or tartaric acid salts) for the treatment of migraine and orthostatic hypotension.

Chemical Information

Molecular Formula
C33H37N5O5
Molecular Mass
583.67740
Charge
0
SMILES
[H][C@@]12Cc3c[nH]c4cccc(c34)[C@@]1([H])C[C@H](CN2C)C(=O)N[C@]1(C)O[C@]2(O)N([C@@H](Cc3ccccc3)C(=O)N3CCC[C@@]23[H])C1=O
InChI
InChI=1S/C33H37N5O5/c1-32(35-29(39)21-15-23-22-10-6-11-24-28(22)20(17-34-24)16-25(23)36(2)18-21)31(41)38-26(14-19-8-4-3-5-9-19)30(40)37-13-7-12-27(37)33(38,42)43-32/h3-6,8-11,17,21,23,25-27,34,42H,7,12-16,18H2,1-2H3,(H,35,39)/t21-,23-,25-,26+,27+,32-,33+/m1/s1
InChIKey
LUZRJRNZXALNLM-JGRZULCMSA-N

Alternative Names

  • (10alphaH)-5'alpha-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman
  • 5'-benzyl-12'-hydroxy-2'-methyl-3',6',18-trioxo-9,10-dihydroergotaman
  • 9,10-dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)ergotoman-3',6',18-trione
  • 9,10-dihydroergotamine
  • dihidroergotamina
  • dihydroergotamine
  • Dihydroergotamine
  • dihydroergotaminum

Drug Classification

Important Medical Information

⚕️ This information is sourced from ChEBI (Chemical Entities of Biological Interest) database and is intended for educational purposes only.

  • Always consult with a healthcare professional before starting, stopping, or modifying any medication.
  • Side effects may vary and this list may not be comprehensive.
  • Drug interactions may occur with other medications.

Additional Identifiers

DRON_00010000
4025
oboInOwl#hasDbXref
Wikipedia:Dihydroergotamine
core#notation
CHEBI:4562

Additional References

Wikipedia:Dihydroergotamine

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Additional Attributes

oboInOwl#hasOBONamespace
chebi_ontology
DRON_00010000
4025
oboInOwl#hasDbXref
Wikipedia:Dihydroergotamine
oboInOwl#id
CHEBI:4562
core#notation
CHEBI:4562
oboInOwl#hasAlternativeId
CHEBI:658566
oboInOwl#inSubset
http://purl.obolibrary.org/obo/chebi#3_STAR
RO_0000087
http://purl.obolibrary.org/obo/CHEBI_51065
22-rdf-syntax-ns#type
http://www.w3.org/2002/07/owl#Class
owl#someValuesFrom
t1102089
rdf-schema#domain
https://w3id.org/def/predibionto#has_side_effect24592
owl#annotatedSource
t221449