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  |
| ATC code | N02CA01 |
| PubChem | CID 10531 |
| DrugBank | APRD00476 |
| ChemSpider | 10091 |
| UNII | 436O5HM03C |
| KEGG | D07837 |
| ChEBI | CHEBI:4562 |
| ChEMBL | CHEMBL1732 |
| 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 |
|
|
 (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, acting as an agonist to the serotonin 5-HT(1D) 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.
[edit] 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[1] . Intravenous injection is considered very effective for severe migraine or status migrainosus. DHE is also used in the treatment of medication overuse headache[2] .
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.[3]
MAP Pharmaceuticals submitted an inhaled version of DHE (Levadex) for FDA approval in May 2011.
[edit] References
- ^ Colman, Ian; Brown, Michael D., Innes, Grant D., Grafstein, Eric, Roberts, Ted E., Rowe, Brian H. (1 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.
- ^ Saper, JR; Silberstein, S, Dodick, D, Rapoport, A (2006 Nov). "DHE in the pharmacotherapy of migraine: potential for a larger role.". Headache 46 Suppl 4: S212-20. PMID 17078853.
- ^ 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.
[edit] External links
|
|
