511-12-6
Chemical Structure
Dihydroergotamine
Synonym(s): DFN-19
- CAS No.: 511-12-6
- Formula:C33H37N5O5
- Molecular Weight:583.68
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
InChIKey: LUZRJRNZXALNLM-JGRZULCMSA-N
SMILES: O[C@@]([C@@](CCC1)([H])N1C2=O)(O[C@](NC([C@@H](CN(C)[C@]3([H])C4)C[C@]3([H])C5=C6C4=CNC6=CC=C5)=O)(C)C7=O)N7[C@H]2CC8=CC=CC=C8
Biological Activity: Dihydroergotamine (DFN-19) is a blood-brain barrier-permeable semi-synthetic ergot alkaloid, acting as a full agonist of 5-HT1B/1D receptors (Ki values of 0.3 nM and 2.5 nM, respectively; functional IC50 values of 2 nM and 2.2 nM, respectively). Dihydroergotamine inhibits Forskolin (HY-15371)-stimulated cAMP accumulation, possesses α-adrenergic receptor antagonistic activity and weak dopaminergic agonistic activity. It mediates intracranial cerebrovascular contraction, inhibits the release of neuropeptides such as CGRP/substance P, and suppresses neurogenic inflammation by activating 5-HT1B/1D receptors in the trigeminovascular system. Dihydroergotamine binds to the catalytic site of Trypanosoma cruzi trypanothione reductase and exhibits trypanocidal activity in vitro. Dihydroergotamine can be used in studies related to migraine and trypanosome infections[1][2][3][4].
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Dihydroergotamine | Dihydroergotamine (DFN-19) is a blood-brain barrier-permeable semi-synthetic ergot alkaloid, acting as a full agonist of 5-HT1B/1D receptors (Ki values of 0.3 nM and 2.5 nM, respectively; functional IC50 values of 2 nM and 2.2 nM, respectively). Dihydroergotamine inhibits Forskolin (HY-15371)-stimulated cAMP accumulation, possesses α-adrenergic receptor antagonistic activity and weak dopaminergic agonistic activity. It mediates intracranial cerebrovascular contraction, inhibits the release of neuropeptides such as CGRP/substance P, and suppresses neurogenic inflammation by activating 5-HT1B/1D receptors in the trigeminovascular system. Dihydroergotamine binds to the catalytic site of Trypanosoma cruzi trypanothione reductase and exhibits trypanocidal activity in vitro. Dihydroergotamine can be used in studies related to migraine and trypanosome infections. | |||||||||||||||||||||
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Dihydroergotamine-d3 | Dihydroergotamine-d3 is the d3-labeled Dihydroergotamine (HY-B0670). Dihydroergotamine (DFN-19) is a blood-brain barrier-permeable semi-synthetic ergot alkaloid, acting as a full agonist of 5-HT1B/1D receptors (Ki values of 0.3 nM and 2.5 nM, respectively; functional IC50 values of 2 nM and 2.2 nM, respectively). Dihydroergotamine inhibits Forskolin (HY-15371)-stimulated cAMP accumulation, possesses α-adrenergic receptor antagonistic activity and weak dopaminergic agonistic activity. It mediates intracranial cerebrovascular contraction, inhibits the release of neuropeptides such as CGRP/substance P, and suppresses neurogenic inflammation by activating 5-HT1B/1D receptors in the trigeminovascular system. Dihydroergotamine binds to the catalytic site of Trypanosoma cruzi trypanothione reductase and exhibits trypanocidal activity in vitro. Dihydroergotamine can be used in studies related to migraine and trypanosome infections. | |||||||||||||||||||||
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- [1]. Lesage AS, et al. Agonistic properties of alniditan, sumatriptan and dihydroergotamine on human 5-HT1B and 5-HT1D receptors expressed in various mammalian cell lines. British journal of pharmacology. 1998 Apr;123(8):1655-65. [Content Brief]
- [2]. Shafqat R, et al. Updated Evaluation of IV Dihydroergotamine (DHE) for Refractory Migraine: Patient Selection and Special Considerations. Journal of pain research. 2020;13:859-864.
- [3]. Zheng Y, et al. Dihydroergotamine protects against ischemic stroke by modulating microglial/macrophage polarization and inhibiting inflammation in mice. Neurological research. 2024 Apr;46(4):367-377.
- [4]. Gómez-Escobedo R, et al. Molecular Docking-Based Virtual Screening of FDA-Approved Drugs Using Trypanothione Reductase Identified New Trypanocidal Agents. Molecules (Basel, Switzerland). 2024 Aug 10;29(16):3796.
