methysergide Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
ergot alkaloid derivatives 1775 361-37-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • deseril
  • methysergide
  • methysergid
  • methysergide maleate
An ergot derivative that is a congener of LYSERGIC ACID DIETHYLAMIDE. It antagonizes the effects of serotonin in blood vessels and gastrointestinal smooth muscle, but has few of the properties of other ergot alkaloids. Methysergide is used prophylactically in migraine and other vascular headaches and to antagonize serotonin in the carcinoid syndrome.
  • Molecular weight: 353.47
  • Formula: C21H27N3O2
  • CLOGP: 2.22
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 2
  • TPSA: 57.50
  • ALOGS: -3.20
  • ROTB: 4

  • Status: OFM

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
4 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Hosey CM, Chan R, Benet LZ
BA (Bioavailability) 13 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Feb. 12, 1962 FDA

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC N02CA04 NERVOUS SYSTEM
ANALGESICS
ANTIMIGRAINE PREPARATIONS
Ergot alkaloids
MeSH PA D002317 Cardiovascular Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018490 Serotonin Agents
MeSH PA D012702 Serotonin Antagonists
MeSH PA D014662 Vasoconstrictor Agents
CHEBI has role CHEBI:48279 serotonin antagonists
CHEBI has role CHEBI:66991 sympatholytics

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Migraine Prevention indication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.6 acidic
pKa2 6.73 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
5-hydroxytryptamine receptor 2B GPCR AGONIST Ki 9.34 SCIENTIFIC LITERATURE IUPHAR
5-hydroxytryptamine receptor 2C GPCR AGONIST Ki 8.34 SCIENTIFIC LITERATURE IUPHAR
5-hydroxytryptamine receptor 1D GPCR ANTAGONIST Ki 8.90 IUPHAR
5-hydroxytryptamine receptor 7 GPCR ANTAGONIST Ki 7.80 IUPHAR
5-hydroxytryptamine receptor 1B GPCR ANTAGONIST Ki 7.60 IUPHAR
5-hydroxytryptamine receptor 6 GPCR ANTAGONIST Ki 6.80 IUPHAR
5-hydroxytryptamine receptor 1E GPCR ANTAGONIST Ki 6.80 IUPHAR
5-hydroxytryptamine receptor 5A GPCR ANTAGONIST Ki 7 IUPHAR
5-hydroxytryptamine receptor 1F GPCR ANTAGONIST Ki 8.20 IUPHAR
D(1A) dopamine receptor GPCR Ki 6.33 DRUG MATRIX
D(2) dopamine receptor GPCR Ki 6.57 DRUG MATRIX
Alpha-2A adrenergic receptor GPCR Ki 6.21 DRUG MATRIX
5-hydroxytryptamine receptor 1A GPCR PARTIAL AGONIST Ki 7.51 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 5.66 DRUG MATRIX
D(3) dopamine receptor GPCR Ki 7.23 DRUG MATRIX
Sigma non-opioid intracellular receptor 1 Membrane receptor IC50 6.04 CHEMBL
Alpha-2C adrenergic receptor GPCR Ki 7.05 PDSP
Histamine H1 receptor GPCR Ki 5.52 PDSP
Muscarinic acetylcholine receptor M3 GPCR Ki 5.33 PDSP
Muscarinic acetylcholine receptor M1 GPCR Ki 5.26 PDSP
Muscarinic acetylcholine receptor M2 GPCR Ki 5.21 PDSP
5-hydroxytryptamine receptor 2A GPCR AGONIST Ki 9.45 SCIENTIFIC LITERATURE
Induced myeloid leukemia cell differentiation protein Mcl-1 Cytosolic other IC50 4.69 CHEMBL
Bcl-2-like protein 1 Cytosolic other IC50 4.65 CHEMBL
5-hydroxytryptamine receptor 1B GPCR Ki 6.97 DRUG MATRIX
5-hydroxytryptamine receptor 7 GPCR Ki 7.90 CHEMBL
Serotonin 2 (5-HT2) receptor GPCR Ki 8.28 CHEMBL
5-hydroxytryptamine receptor 2A GPCR Ki 8.80 CHEMBL
Cytoplasmic zinc-finger protein Unclassified EC50 4.99 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 7.27 CHEMBL
Zinc finger protein mex-5 Cytosolic other EC50 4.91 CHEMBL
5-hydroxytryptamine receptor 1F Unclassified ANTAGONIST IC50 7.80 IUPHAR
5-hydroxytryptamine receptor 7 GPCR ANTAGONIST Ki 7.90 IUPHAR
5-hydroxytryptamine receptor 5A Unclassified ANTAGONIST Ki 7.20 IUPHAR
5-hydroxytryptamine receptor 5A Unclassified ANTAGONIST Ki 6.70 IUPHAR
5-hydroxytryptamine receptor 6 GPCR ANTAGONIST Ki 6.60 IUPHAR

External reference:

IDSource
D00681 KEGG_DRUG
129-49-7 SECONDARY_CAS_RN
4018758 VANDF
4019833 VANDF
C0025842 UMLSCUI
CHEBI:92629 CHEBI
H8J PDB_CHEM_ID
CHEMBL485253 ChEMBL_ID
CHEMBL1065 ChEMBL_ID
CHEMBL3989558 ChEMBL_ID
CHEMBL1200938 ChEMBL_ID
D008784 MESH_DESCRIPTOR_UI
DB00247 DRUGBANK_ID
4163 PUBCHEM_CID
134 IUPHAR_LIGAND_ID
1000 INN_ID
XZA9HY6Z98 UNII
203190 RXNORM
1450 MMSL
5097 MMSL
d00821 MMSL
003414 NDDF
004806 NDDF
11796006 SNOMEDCT_US
20340009 SNOMEDCT_US
387044000 SNOMEDCT_US

Pharmaceutical products:

None