dihydroergotamine   Click here for help

GtoPdb Ligand ID: 121

Synonyms: D.H.E. 45® | Migranal®
Approved drug PDB Ligand
dihydroergotamine is an approved drug (FDA (1997))
Compound class: Synthetic organic
Comment: Dihydroergotamine is an ergot alkaloid. It is used as a vasoconstrictor. The drug is administered as dihydroergotamine mesylate (PubChem CID 71171). The use of ergot alkaloids in the clinic has been discontinued or restricted due to their propensity to cause fibrosis.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 118.21
Molecular weight 583.28
XLogP 2.29
No. Lipinski's rules broken 0
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Canonical SMILES CN1CC(CC2C1Cc1c[nH]c3c1c2ccc3)C(=O)NC1(C)OC2(N(C1=O)C(Cc1ccccc1)C(=O)N1C2CCC1)O
Isomeric SMILES CN1C[C@@H](C[C@H]2[C@H]1Cc1c[nH]c3c1c2ccc3)C(=O)N[C@]1(C)O[C@@]2(N(C1=O)[C@@H](Cc1ccccc1)C(=O)N1[C@H]2CCC1)O
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1997))
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
2022 dihydroergotamine
Synonyms Click here for help
D.H.E. 45® | Migranal®
Database Links Click here for help
Specialist databases
GPCRdb Ligand dihydroergotamine
Other databases
CAS Registry No. 6190-39-2
ChEMBL Ligand CHEMBL1732
DrugBank Ligand DB00320
DrugCentral Ligand 888
GtoPdb PubChem SID 135650182
PubChem CID 10531
Search Google for chemical match using the InChIKey LUZRJRNZXALNLM-JGRZULCMSA-N
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UniChem Compound Search for chemical match using the InChIKey LUZRJRNZXALNLM-JGRZULCMSA-N
UniChem Connectivity Search for chemical match using the InChIKey LUZRJRNZXALNLM-JGRZULCMSA-N
Wikipedia Dihydroergotamine