Dihydroergotamine

Dihydroergotamine
Dihydroergotamine
Systematic (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
Clinical data
Trade names D/h/e/45, Migranal
AHFS/Drugs.com monograph
MedlinePlus a603022
Licence data US FDA:link
Pregnancy cat. X(US)
Legal status ℞-only (US)
Routes nasal spray, SC, IM, IV
Pharmacokinetic data
Half-life 9 hours
Excretion Bile
Identifiers
CAS number 511-12-6 YesY
ATC code N02CA01
PubChem CID 10531
DrugBank APRD00476
ChemSpider 10091 YesY
UNII 436O5HM03C YesY
KEGG D07837 YesY
ChEBI CHEBI:4562 YesY
ChEMBL CHEMBL1732 YesY
Synonyms (5'α)-9,10-dihydro-12'-hydroxy-2'-methyl-5'-(phenylmethyl)-ergotaman-3',6',18-trione
Chemical data
Formula C33H37N5O5 
Mol. mass 583.678 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Dihydroergotamine (/daɪˌhaɪdroʊ.ɜrˈɡɒtəmiːn/ dy-hy-droh-ur-got-ə-meen; brand names D.H.E. 45 and Migranal) 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 but also interacts centrally with dopamine and adrenergic receptors. It can be used to treat acute intractable headache or withdrawal from analgesics.

Description

Dihydroergotamine (DHE) is a semi-synthetic form of ergotamine approved in the US in 1946. Oral bioavailability is poor and it is not available in oral form in the US. DHE is available as Migranal nasal spray and in ampules for subcutaneous, intramuscular and intravenous injection. Efficacy is variable in the nasal spray form with bioavailability 32% of injectable administration. Subcutaneous and intramuscular injections are generally more effective than the nasal spray and can be self-administered by patients. Intravenous injection is considered very effective for severe migraine or status migrainosus. DHE is also used in the treatment of medication overuse headache.

Nausea is a common side effect of IV administration and less common in other modes. Antiemetics can be given prior to DHE to counteract the nausea. Risks and contraindications are similar to the triptans. DHE and triptans should not be taken within 24 hours of each other due to the potential for coronary artery vasospasm. DHE produces no dependence.[1]

MAP Pharmaceuticals submitted an inhaled version of DHE (Levadex) for FDA approval in May 2011.

References

  1. ^ Schaerlinger B, Hickel P, Etienne N, Guesnier L, Maroteaux L (September 2003). "Agonist actions of dihydroergotamine at 5-HT2B and 5-HT2C receptors and their possible relevance to antimigraine efficacy". British journal of pharmacology 140 (2): 277–84. doi:10.1038/sj.bjp.0705437. PMC 1574033. PMID 12970106. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1574033. 

External links

v · d · eAntimigraine preparations (N02C)
Analgesic/abortive
Serotonin modulators
Ergot alkaloids
Dihydroergotamine • Ergotamine • Methysergide • Lisuride
Other
Other
Prevention of migraines
valproate • carbamazepine • oxcarbazepine
Ungrouped
Pizotifen • Iprazochrome • Dimetotiazine • Oxetorone • Lomerizine • Telcagepant

M: CNS

anat(n/s/m/p/4/e/b/d/c/a/f/l/g)/phys/devp

noco(m/d/e/h/v/s)/cong/tumr, sysi/epon, injr

proc, drug(N1A/2AB/C/3/4/7A/B/C/D)
v · d · eErgolines
Lysergic acid derivatives
2-Bromo-LSD (BOL-148) • Bromocriptine • Cabergoline • Dihydroergocornine • Dihydroergocristine • Dihydroergocryptine • Dihydroergometrine (Dihydroergonovine, Dihydroergobasine) • Dihydroergotamine • Dihydroergotoxine • Ergine (LSA; LA-111; Lysergamide) • Ergocornine • Ergocristine • Ergocryptine • Ergoloid • Ergometrine (Ergonovine, Ergobasine) • Ergometrinine • Ergotamine • Ergotoxine • Ergovaline • Lisuride • LSD • LSH • Lysergic Acid • Lysergic acid cyclobutylamide • Lysergic acid cyclopentylamide • Lysergic Acid Methyl Ester • Lysergol • Mesulergine • Metergoline • Methergine (Methylergometrine, Methylergonovine, Methylergobasine) • Methysergide • Pergolide • Syntometrine
Psychedelic lysergamides
AL-LAD • ALD-52 • BU-LAD • CYP-LAD • DAL • DAM-57 • Ergonovine • ETH-LAD • IP-LAD • LAE-32 • LSD • LPD-824 • LSM-775 • LSH • LSD-Pip • Lysergic Acid 2-Butylamide • Lysergic Acid 2,4-Dimethylazetidide • Lysergic Acid 3-Pentylamide • Methylergonovine • Methylisopropyllysergamide • MLD-41 • PARGY-LAD • PRO-LAD
Other ergolines
Natural sources
Achnatherum robustum (Sleepy Grass) • Argyreia nervosa (Hawaiian Baby Woodrose) • Claviceps spp. (Ergot) • Ipomoea spp. (Morning Glory, Tlitliltzin, Badoh Negro) • Rivea corymbosa (Coaxihuitl, Ololiúqui)

Wikimedia Foundation. 2010.

Игры ⚽ Нужно решить контрольную?

Look at other dictionaries:

  • Dihydroergotamine — Général No CAS …   Wikipédia en Français

  • dihydroergotamine — ● dihydroergotamine nom féminin Alcaloïde vasoconstricteur obtenu par hydrogénation de l ergotamine et utilisé dans le traitement des migraines et des insuffisances veineuses …   Encyclopédie Universelle

  • dihydroergotamine — noun Date: 1945 a hydrogenated derivative C33H37N5O5 of ergotamine that is used in the treatment of migraine …   New Collegiate Dictionary

  • dihydroergotamine — /duy huy droh err got euh meen , min, err geuh tam een, in/, n. Pharm. an ergot alkaloid, C33H37N5O5, used in the treatment of various types of migraine headache. [1940 45; DI 1 + HYDRO 2 + ERGOTAMINE] * * * …   Universalium

  • dihydroergotamine — noun An ergot alkaloid used to treat migraines, believed to act upon serotonin receptors …   Wiktionary

  • dihydroergotamine — An ergot alkaloid derivative prepared by the hydrogenation of ergotamine; used in the treatment of migraine; less toxic and less oxytocic than ergotamine. * * * di·hy·dro·er·got·a·mine .ər gät ə .mēn …   Medical dictionary

  • dihydroergotamine — n. methanesulfonate, crystalline compound used as a medication for migraine headaches …   English contemporary dictionary

  • dihydroergotamine — di·hy·dro·ergotamine …   English syllables

  • dihydroergotamine — |dīˌh]īdrō, dī|h]+ noun Etymology: International Scientific Vocabulary dihydr + ergotamine : a crystalline compound C33H37N5O5 made by hydrogenating ergotamine and used in the treatment of migraine headaches * * * /duy huy droh err got euh meen …   Useful english dictionary

  • dihydroergotamine mesylate — di·hy·dro·er·got·amine mes·y·late (di hi″dro ər gotґə mēn) [USP] an antiadrenergic produced by the catalytic hydrogenation of ergotamine; used as a vasoconstrictor in the treatment of migraine; administered intramuscularly,… …   Medical dictionary

Share the article and excerpts

Direct link
… Do a right-click on the link above
and select “Copy Link”