2GM

Dihydroergotamine

Created: 2013-01-17
Last modified:  2013-03-13

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Chemical Details

Formal Charge0
Atom Count80
Chiral Atom Count7
Bond Count87
Aromatic Bond Count16
2D diagram of 2GM

Chemical Component Summary

NameDihydroergotamine
Systematic Name (OpenEye OEToolkits)n/a
FormulaC33 H37 N5 O5
Molecular Weight583.677
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O=C6N7C(C(=O)N1CCCC1C7(O)OC6(NC(=O)C4CC5c2cccc3c2c(cn3)CC5N(C)C4)C)Cc8ccccc8
SMILESCACTVS3.370CN1C[CH](C[CH]2[CH]1Cc3c[nH]c4cccc2c34)C(=O)N[C]5(C)O[C]6(O)[CH]7CCCN7C(=O)[CH](Cc8ccccc8)N6C5=O
SMILESOpenEye OEToolkits1.7.6CC1(C(=O)N2C(C(=O)N3CCCC3C2(O1)O)Cc4ccccc4)NC(=O)C5CC6c7cccc8c7c(c[nH]8)CC6N(C5)C
Canonical SMILESCACTVS3.370 CN1C[C@@H](C[C@H]2[C@H]1Cc3c[nH]c4cccc2c34)C(=O)N[C@]5(C)O[C@@]6(O)[C@@H]7CCCN7C(=O)[C@H](Cc8ccccc8)N6C5=O
Canonical SMILESOpenEye OEToolkits1.7.6 C[C@@]1(C(=O)N2[C@H](C(=O)N3CCC[C@H]3[C@@]2(O1)O)Cc4ccccc4)NC(=O)[C@@H]5C[C@@H]6c7cccc8c7c(c[nH]8)C[C@H]6N(C5)C
InChIInChI1.03 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
InChIKeyInChI1.03 LUZRJRNZXALNLM-JGRZULCMSA-N

Drug Info: DrugBank

DrugBank IDDB00320 
NameDihydroergotamine
Groups
  • investigational
  • approved
DescriptionA 9,10alpha-dihydro derivative of [ergotamine]. Dihydroergotamine is used as an abortive therapy for migraines.[L38469] Its use has largely been supplanted by triptans in current therapy due to the class's greater selectivity and more favourable side effect profile. Recent improvements have been made in the design of intranasal delivery devices allowing for greater delivery of dihydroergotamine solution to the vasculature-rich upper nasal cavity.[A239569] The recently approved Precision Olfactory Delivery technology developed by Impel Neuropharma technology has correlated with an increase of 3-fold in Cmax and 4-fold in AUC despite the solution formulated at 75% of the strength of the existing intranasal product.
Synonyms
  • Diidroergotamina
  • (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
  • Dihydroergotamin
  • Dihydroergotamine
  • Dihydroergotamine tartrate
Brand Names
  • PMS-dihydroergotamine
  • Trudhesa
  • Dromelate
  • Dihydroergotamine (dhe), 1mg/ml
  • Dihydroergotamine mesylate
IndicationDihydroergotamine (DHE) in all formulations is indicated for the acute treatment of migraine with or without aura in adults.[L38459, L38464, L38469] As an injection, DHE is also indicated for the acute treatment of cluster headache episodes.[L38459] DHE is not indicated for migraine prevention or the management of hemiplegic or basilar migraine.[L38459, L38464, L38469]
Categories
  • Adrenergic alpha-1 Receptor Antagonists
  • Adrenergic alpha-Antagonists
  • Adrenergic Antagonists
  • Agents that produce hypertension
  • Alkaloids
ATC-Code
  • N02CA51
  • N02CA01
CAS number511-12-6

Drug Targets

NameTarget SequencePharmacological ActionActions
5-hydroxytryptamine receptor 1BMEEPGAQCAPPPPAGSETWVPQANLSSAPSQNCSAKDYIYQDSISLPWKV...unknownagonist
5-hydroxytryptamine receptor 1DMSPLNQSAEGLPQEASNRSLNATETSEAWDPRTLQALKISLAVVLSVITL...unknownagonist
5-hydroxytryptamine receptor 1FMDFLNSSDQNLTSEELLNRMPSKILVSLTLSGLALMTTTINSLVIAAIIV...unknownagonist
Alpha-2A adrenergic receptorMGSLQPDAGNASWNGTEAPGGGARATPYSLQVTLTLVCLAGLLMLLTVFG...unknownagonist
5-hydroxytryptamine receptor 1AMDVLSPGQGNNTTSPPAPFETGGNTTGISDVTVSYQVITSLLLGTLIFCA...unknownagonist
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1732
PubChem 10531
ChEMBL CHEMBL1732
ChEBI CHEBI:4562
CCDC/CSD HERGOM