Dihydroergotamine

Dihydroergotamine
Clinical data
Pronunciation	/daɪˌhaɪdroʊ.ɜːrˈɡɒtəmiːn/ dy-HY-droh-ur-GOT-ə-meen
Trade names	D.H.E. 45, others
Other names	DHE; (5'α)-9,10-Dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)-ergotaman-3',6',18-trione
AHFS/Drugs.com	Monograph
MedlinePlus	a603022
License data	US DailyMed: Dihydroergotamine;
Routes of; administration	Nasal, subcutaneous, intramuscular, intravenous
ATC code	N02CA01 (WHO) ;
Legal status
Legal status	BR: Class D1 (Drug precursors); US: ℞-only;
Pharmacokinetic data
Bioavailability	32% (nasal spray)
Elimination half-life	9 hours
Excretion	Bile duct
Identifiers
	IUPAC name (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;
CAS Number	511-12-6; mesylate: 6190-39-2;
PubChem CID	10531;
IUPHAR/BPS	121;
DrugBank	DB00320; mesylate: DBSALT000997;
ChemSpider	10091; mesylate: 64311;
UNII	436O5HM03C; mesylate: 81AXN7R2QT;
KEGG	D07837; mesylate: D02211;
ChEBI	CHEBI:4562; mesylate: CHEBI:59756;
ChEMBL	ChEMBL1732; mesylate: ChEMBL1200517;
CompTox Dashboard (EPA)	DTXSID6045614 ;
ECHA InfoCard	100.007.386
Chemical and physical data
Formula	C33H37N5O5
Molar mass	583.689 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [H][C@]56C[C@@H](C(=O)N[C@]1(C)O[C@]4(O)N(C1=O)[C@@H](Cc2ccccc2)C(=O)N3CCC[C@]34[H])CN(C)[C@]5([H])Cc7c[nH]c8cccc6c78;
	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; Key:LUZRJRNZXALNLM-JGRZULCMSA-N;

Dihydroergotamine (DHE), sold under the brand names D.H.E. 45 and Migranal among others, is an ergot alkaloid used to treat migraines.^[8] 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.^[9]

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.

^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.
^ "D.H.E. 45- dihydroergotamine mesylate injection, solution". DailyMed. Retrieved 31 October 2021.
^ "Migranal- dihydroergotamine mesylate spray". DailyMed. Retrieved 31 October 2021.
^ "Dromelate- dihydroergotamine mesylate injection, solution". DailyMed. Retrieved 31 October 2021.
^ "Trudhesa- dihydroergotamine mesylate spray, metered". DailyMed. Retrieved 31 October 2021.
^ Cite error: The named reference Atzumi FDA label was invoked but never defined (see the help page).
^ Cite error: The named reference Brekiya FDA label was invoked but never defined (see the help page).
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 340–. ISBN 978-3-88763-075-1.
^ Colman I, Brown MD, Innes GD, Grafstein E, Roberts TE, Rowe BH (April 2005). "Parenteral dihydroergotamine for acute migraine headache: a systematic review of the literature". Annals of Emergency Medicine. 45 (4): 393–401. doi:10.1016/j.annemergmed.2004.07.430. PMID 15795718.

[1] Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.

[2] "D.H.E. 45- dihydroergotamine mesylate injection, solution". DailyMed. Retrieved 31 October 2021.

[Migranal_FDA_label-3] "Migranal- dihydroergotamine mesylate spray". DailyMed. Retrieved 31 October 2021.

[Dromelate_FDA_label-4] "Dromelate- dihydroergotamine mesylate injection, solution". DailyMed. Retrieved 31 October 2021.

[Trudhesa_FDA_label-5] "Trudhesa- dihydroergotamine mesylate spray, metered". DailyMed. Retrieved 31 October 2021.

[Atzumi_FDA_label-6] Cite error: The named reference Atzumi FDA label was invoked but never defined (see the help page).

[Brekiya_FDA_label-7] Cite error: The named reference Brekiya FDA label was invoked but never defined (see the help page).

[IndexNominum2000-8] Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 340–. ISBN 978-3-88763-075-1.

[Colman-9] Colman I, Brown MD, Innes GD, Grafstein E, Roberts TE, Rowe BH (April 2005). "Parenteral dihydroergotamine for acute migraine headache: a systematic review of the literature". Annals of Emergency Medicine. 45 (4): 393–401. doi:10.1016/j.annemergmed.2004.07.430. PMID 15795718.

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