dihydroergotamine

Also known as DHE111, D.H.E. 45®, Migranal®, 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, (2R,4R,7R)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),9,12,14-tetraene-4-carboxamide, Dihydroergotamin

Dihydroergotamine (DHE), sold under the brand names D.H.E. 45 and Migranal among others, is an ergot alkaloid used to treat migraines. It is a derivative of ergotamine. It is administered as a nasal spray or injection and has an efficacy similar to that of sumatriptan. Nausea is a common side effect.

In the Vinony graph

Vinony's link graph records 2,389 inbound references to dihydroergotamine, and connects out to ergoline, propranolol and adrenergic receptor.

Vinony files it under 5-HT1A agonists, 5-HT2B agonists and Alpha-1 blockers.

Vinony links it to 17 Wikipedia language editions.

Key facts

Drug.image: Dihydroergotamine.svg
Drug.image_class: skin-invert-image
Drug.width: 200px
Drug.image2: Dihydroergotamine 3D.png
Drug.image_class2: bg-transparent
Drug.width2: 225px
Drug.tradename: D.H.E. 45, others
Drug.MedlinePlus: a603022
Drug.DailyMedID: Dihydroergotamine
Drug.routes_of_administration: Nasal, subcutaneous, intramuscular, intravenous
Drug.ATC_prefix: N02
Drug.ATC_suffix: CA01
Drug.legal_BR: D1
Drug.legal_US: Rx-only
Drug.bioavailability: 32% (nasal spray)
Drug.elimination_half life: 9 hours
Drug.excretion: Bile duct
Drug.index2_label: mesylate

via Wikipedia infobox

Chemical data

Formula: C33H37N5O5
Molecular weight: 583.7 g/mol
IUPAC name: (6aR,9R,10aR)-N-[(1S,2S,4R,7S)-7-benzyl-2-hydroxy-4-methyl-5,8-dioxo-3-oxa-6,9-diazatricyclo[7.3.0.02,6]dodecan-4-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
SMILES: C[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)CC4=CC=CC=C4)NC(=O)[C@@H]5C[C@H]6[C@@H](CC7=CNC8=CC=CC6=C78)N(C5)C
InChIKey: LUZRJRNZXALNLM-JGRZULCMSA-N
XLogP: 2.4
Polar surface area: 118 Å²
H-bond donors: 3
H-bond acceptors: 6
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1946
Admin. routes: parenteral, topical
Indications: migraine disorder, migraine with aura, migraine without aura

via ChEMBL · EBI

Research

2,055 papers

via PubMed

Wikidata facts

Has part: carbon
Mass: 583.279
Has use: medication

Show 10 more facts

significant drug interaction: ritonavir
Commons category: Dihydroergotamine
chemical formula: C₃₃H₃₇N₅O₅
medical condition treated: orthostatic hypotension
World Health Organisation international non-proprietary name: dihydroergotamine
isomeric SMILES: C[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)CC4=CC=CC=C4)NC(=O)[C@@H]5C[C@H]6[C@@H](CC7=CNC8=CC=CC6=C78)N(C5)C
canonical SMILES: CC1(C(=O)N2C(C(=O)N3CCCC3C2(O1)O)CC4=CC=CC=C4)NC(=O)C5CC6C(CC7=CNC8=CC=CC6=C78)N(C5)C
subject has role: dopamine agonist
defined daily dose: 4
legal status (medicine): boxed warning

Sources (6)

via Wikidata · CC0

~5 min read

Encyclopedic overview

11 sections

Contents

Medical uses
Contraindications
Side effects
Pharmacology
Pharmacodynamics
Pharmacokinetics
History
Society and culture
Legal status
Brand names
References

It has similar actions to the triptans, acting as an agonist to the serotonin receptors and causing vasoconstriction of the intracranial blood vessels, but also interacts centrally with dopamine and adrenergic receptors. It can be used to treat acute intractable headache or withdrawal from analgesics.

Excerpted from Wikipedia’s “dihydroergotamine” article, available under the CC BY-SA 4.0 licence.