methysergide   Click here for help

GtoPdb Ligand ID: 134

Synonyms: 1-methylmethylergonovine | Deseril® | Sansert® | UML-491
Approved drug PDB Ligand
methysergide is an approved drug (FDA (1962))
Compound class: Synthetic organic
Comment: Methysergide is an ergot alkaloid. When used, this drug is administered as methysergide maleate (PubChem CID 5281073). The use of ergot alkaloids 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 4
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 57.5
Molecular weight 353.21
XLogP 1.84
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CCC(NC(=O)C1CN(C)C2C(=C1)c1cccc3c1c(C2)cn3C)CO
Isomeric SMILES CC[C@H](NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)cn3C)CO
InChI InChI=1S/C21H27N3O2/c1-4-15(12-25)22-21(26)14-8-17-16-6-5-7-18-20(16)13(10-23(18)2)9-19(17)24(3)11-14/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26)/t14-,15+,19-/m1/s1
InChI Key KPJZHOPZRAFDTN-ZRGWGRIASA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1962))
Withdrawn drug? Yes
IUPAC Name Click here for help
(4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
International Nonproprietary Names Click here for help
INN number INN
1000 methysergide
Synonyms Click here for help
1-methylmethylergonovine | Deseril® | Sansert® | UML-491
Database Links Click here for help
BindingDB Ligand 50031942
CAS Registry No. 361-37-5
ChEBI CHEBI:238605
ChEMBL Ligand CHEMBL1065
DrugBank Ligand DB00247
DrugCentral Ligand 1775
GtoPdb PubChem SID 135650596
PubChem CID 9681
RCSB PDB Ligand H8J
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Wikipedia Methysergide