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511-12-6-Dihydroergotamine Dihydroergotamine

Dihydroergotamine

For research use only. Not for therapeutic Use.

  • CAT Number: I026147
  • CAS Number: 511-12-6
  • Molecular Formula: C33H37N5O5
  • Molecular Weight: 583.68
  • Purity: 98%
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Related Small Molecules: Kif15-IN-2     Nicorandil-d4     BBS-4    

Dihydroergotamine is a 9,10alpha-dihydro derivative of ERGOTAMINE. It is used as a vasoconstrictor, specifically for the therapy of MIGRAINE DISORDERS.


Catalog Number I026147
CAS Number 511-12-6
Synonyms

Dihydroergotamine; MAP0004; DHE; MAP 0004; MAP-0004; Levadex;

Molecular Formula C33H37N5O5
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name (6aR,9R,10aR)-N-((2R,5S,10aS,10bS)-5-benzyl-10b-hydroxy-2-methyl-3,6-dioxooctahydro-8H-oxazolo[3,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxamide
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
InChIKey LUZRJRNZXALNLM-JGRZULCMSA-N
SMILES [H][C@@]12CC3=CNC4=C3C([C@@]1([H])C[C@@H](C(N[C@@]5(C)C(N6[C@@H](CC7=CC=CC=C7)C(N8CCC[C@]8([C@]6(O)O5)[H])=O)=O)=O)CN2C)=CC=C4
Reference

1: Tfelt-Hansen PC, Diener HC. Use of dihydroergotamine (DHE) should be restricted to no more than twice a week. Headache. 2014 Oct;54(9):1523-5. doi: 10.1111/head.12389. Epub 2014 May 26. Review. PubMed PMID: 24862945.
2: Nagy AJ, Gandhi S, Bhola R, Goadsby PJ. Intravenous dihydroergotamine for inpatient management of refractory primary headaches. Neurology. 2011 Nov 15;77(20):1827-32. doi: 10.1212/WNL.0b013e3182377dbb. Epub 2011 Nov 2. PubMed PMID: 22049203.
3: Silberstein SD, Kori SH. Dihydroergotamine: a review of formulation approaches for the acute treatment of migraine. CNS Drugs. 2013 May;27(5):385-94. doi: 10.1007/s40263-013-0061-2. Review. PubMed PMID: 23620146.
4: Tfelt-Hansen P. Is orally inhaled dihydroergotamine (DHE) equivalent in efficacy in migraine to intravenous DHE? Headache. 2014 Feb;54(2):383. doi: 10.1111/head.12269. PubMed PMID: 24512579.
5: Tepper SJ. Orally inhaled dihydroergotamine: a review. Headache. 2013 Sep;53 Suppl 2:43-53. doi: 10.1111/head.12184. Review. PubMed PMID: 24024602.
6: Kellerman DJ, Forst A, Combs DL, Borland S, Kori S. Assessment of the consistency of absorption of dihydroergotamine following oral inhalation: pooled results from four clinical studies. J Aerosol Med Pulm Drug Deliv. 2013 Oct;26(5):297-306. doi: 10.1089/jamp.2012.0999. Epub 2012 Dec 28. PubMed PMID: 23273242.
7: Lambru G, Shanahan P, Matharu M. Exacerbation of SUNCT and SUNA syndromes during intravenous dihydroergotamine treatment: A case series. Cephalalgia. 2015 Oct;35(12):1115-24. doi: 10.1177/0333102415570495. Epub 2015 Feb 9. PubMed PMID: 25667300.
8: Tfelt-Hansen PC. Relatively slow and long-lasting antimigraine effect of dihydroergotamine is most likely due to basic pharmacological attributes of the drug: a review. Cephalalgia. 2013 Oct;33(13):1122-31. doi: 10.1177/0333102413483372. Epub 2013 Apr 15. Review. PubMed PMID: 23588793.
9: Noveck RJ, Douglas PS, Chow SC, Mangum B, Kori S, Kellerman DJ. Assessing acute systemic effects of an inhaled drug with serial echocardiography: a placebo-controlled comparison of inhaled and intravenous dihydroergotamine. Drug Des Devel Ther. 2013 Jul 24;7:619-25. doi: 10.2147/DDDT.S44093. Print 2013. PubMed PMID: 23926420; PubMed Central PMCID: PMC3728267.
10: Eller M, Gelfand AA, Riggins NY, Shiboski S, Schankin C, Goadsby PJ. Exacerbation of headache during dihydroergotamine for chronic migraine does not alter outcome. Neurology. 2016 Mar 1;86(9):856-9. doi: 10.1212/WNL.0000000000002406. Epub 2016 Feb 3. PubMed PMID: 26843569; PubMed Central PMCID: PMC4793780.
11: Marichal-Cancino BA, González-Hernández A, Manrique-Maldonado G, Ruiz-Salinas II, Altamirano-Espinoza AH, MaassenVanDenBrink A, Villalón CM. Intrathecal dihydroergotamine inhibits capsaicin-induced vasodilatation in the canine external carotid circulation via GR127935- and rauwolscine-sensitive receptors. Eur J Pharmacol. 2012 Oct 5;692(1-3):69-77. doi: 10.1016/j.ejphar.2012.07.033. Epub 2012 Jul 27. PubMed PMID: 22841658.
12: Bauermeister A, Aguiar FA, Marques LM, Malta JD Jr, Barros F, Callejon DR, de Oliveira AR, Lopes NP. In Vitro Metabolism Evaluation of the Ergot Alkaloid Dihydroergotamine: Application of Microsomal and Biomimetic Oxidative Model. Planta Med. 2016 Oct;82(15):1368-1373. Epub 2016 Aug 2. PubMed PMID: 27485816.
13: Chou DE, Tso AR, Goadsby PJ. Aprepitant for the management of nausea with inpatient IV dihydroergotamine. Neurology. 2016 Oct 11;87(15):1613-1616. Epub 2016 Sep 14. PubMed PMID: 27629088; PubMed Central PMCID: PMC5067541.
14: Dahlöf C, Maassen Van Den Brink A. Dihydroergotamine, ergotamine, methysergide and sumatriptan – basic science in relation to migraine treatment. Headache. 2012 Apr;52(4):707-14. doi: 10.1111/j.1526-4610.2012.02124.x. Epub 2012 Mar 22. Review. PubMed PMID: 22444161.
15: Charles A. Comment: Outcomes of migraine therapy with IV dihydroergotamine. Neurology. 2016 Mar 1;86(9):859. doi: 10.1212/WNL.0000000000002408. Epub 2016 Feb 3. PubMed PMID: 26843565.
16: Robbins NM, Ito H, Scheinman MM, Goadsby PJ. Safety of domperidone in treating nausea associated with dihydroergotamine infusion and headache. Neurology. 2016 Dec 13;87(24):2522-2526. Epub 2016 Nov 11. PubMed PMID: 27837002; PubMed Central PMCID: PMC5206996.
17: Bekan G, Tfelt-Hansen P. Is the Generally Held View That Intravenous Dihydroergotamine Is Effective in Migraine Based on Wrong "General Consensus" of One Trial? A Critical Review of the Trial and Subsequent Quotations. Headache. 2016 Oct;56(9):1482-1491. doi: 10.1111/head.12904. Epub 2016 Sep 6. Review. PubMed PMID: 27595607.
18: Silberstein S. MAP0004: dihydroergotamine mesylate inhalation aerosol for acute treatment of migraine. Expert Opin Pharmacother. 2012 Sep;13(13):1961-8. doi: 10.1517/14656566.2012.711319. Epub 2012 Aug 4. Review. PubMed PMID: 22860628.
19: Schenkat DH, Schulz LT, Johnson BD. Dihydroergotamine-induced vasospastic angina in a patient taking a calcium channel blocker. Ann Pharmacother. 2011 Jul;45(7-8):e41. doi: 10.1345/aph.1P776. Epub 2011 Jun 21. PubMed PMID: 21693700.
20: Bérard A, Kori S. Dihydroergotamine (DHE) use during gestation and the risk of adverse pregnancy outcomes. Headache. 2012 Jul-Aug;52(7):1085-93. doi: 10.1111/j.1526-4610.2012.02172.x. Epub 2012 May 21. PubMed PMID: 22612391.

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