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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

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

Additional References

Wikipedia:Dihydroergotamine

🔍 Click on any linked disease name to learn more about the conditions this medication is used to treat, or explore related drug classifications for more information about similar medications.

Additional Attributes

listing_expiration_date
20241231
marketing_start_date
19971208
route
NASAL
spl_id
266a0914-df98-c5f3-e063-6394a90a95c5
package_ndc
81284-411-10
package_description
10 AMPULE in 1 CARTON (81284-411-10) / 1 mL in 1 AMPULE (81284-411-00)
labeler_name
Teva Czech Industries s.r.o
core#notation
CHEBI:4562
rxcui
2569842
package_marketing_start_date
19971208
manufacturer_name
Impel Pharmaceuticals Inc.
active_ingredient_strength
100 kg/100kg
active_ingredient_name
DIHYDROERGOTAMINE
pharm_class
Ergotamines [CS]
unii
81AXN7R2QT
spl_set_id
40b9ba9e-436e-444e-b078-01b12bb57ea7
upc
0381284411103
22-rdf-syntax-ns#type
http://www.w3.org/2002/07/owl#Class
oboInOwl#hasOBONamespace
chebi_ontology
DRON_00010000
4025
oboInOwl#hasDbXref
Wikipedia:Dihydroergotamine
oboInOwl#id
CHEBI:4562
oboInOwl#hasAlternativeId
CHEBI:658566
generic_name
dihydroergotamine mesylate
product_type
BULK INGREDIENT
marketing_category
BULK INGREDIENT FOR HUMAN PRESCRIPTION COMPOUNDING
dosage_form
SPRAY, METERED
brand_name
Trudhesa
brand_name_base
Trudhesa
product_ndc
81284-411
application_number
ANDA212046
oboInOwl#inSubset
http://purl.obolibrary.org/obo/chebi#3_STAR
RO_0000087
http://purl.obolibrary.org/obo/CHEBI_51065
owl#someValuesFrom
t1102089
rdf-schema#domain
https://w3id.org/def/predibionto#has_side_effect24592
owl#annotatedSource
t221449