Dihydroergotamine

Dihydroergotamine
Clinical data
Pronunciation	/daɪˌhaɪdroʊ.ɜːrˈɡɒtəmiːn/ dy-HY-droh-ur-GOT-ə-meen
Trade names	D.H.E. 45, Migranal, Trudhesa, 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 FDA: 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
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 ;
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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.

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.

Clinical data

Pronunciation	/daɪˌhaɪdroʊ.ɜːrˈɡɒtəmiːn/ dy-HY-droh-ur-GOT-ə-meen
Trade names	D.H.E. 45, Migranal, Trudhesa, 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 FDA: 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
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[7.3.0.0^2,6]dodecan-4-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,7.0^12,16]hexadeca-1(16),9,12,14-tetraene-4-carboxamide
CAS Number	511-12-6^Y mesylate: 6190-39-2^Y
PubChem CID	10531
IUPHAR/BPS	121
DrugBank	DB00320^Y mesylate: DBSALT000997
ChemSpider	10091^Y mesylate: 64311
UNII	436O5HM03C mesylate: 81AXN7R2QT^Y
KEGG	D07837^Y mesylate: D02211
ChEBI	CHEBI:4562^Y mesylate: CHEBI:59756
ChEMBL	ChEMBL1732^Y 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^Y Key:LUZRJRNZXALNLM-JGRZULCMSA-N^Y
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