Identification

Name
Methysergide
Accession Number
DB00247  (APRD00463)
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
  • (+)-9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8beta-carboxamide
  • (+)-N-(1-(Hydroxymethyl)propyl)-1-methyl-D-lysergamide
  • 1-Methyl-D-lysergic acid butanolamide
  • 1-Methyl-dextro-lysergic acid (+)-1-hydroxy-2-butylamide
  • 1-Methyllysergic acid butanolamide
  • 1-Methylmethylergonovine
  • 9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8-carboxamide
  • Methysergide
  • Methysergidum
  • Metisergida
  • Metisergido
  • N-(1-(Hydroxymethyl)propyl)-1-methyl-dextro-(+)-lysergamide
Product Ingredients
IngredientUNIICASInChI Key
Methysergide maleate2U7H1466GH129-49-7LWYXFDXUMVEZKS-ZVFOLQIPSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
SansertTablet2 mgOralNovartis1962-12-312009-02-16Canada
International/Other Brands
Deseril / Desernil
Categories
UNII
XZA9HY6Z98
CAS number
361-37-5
Weight
Average: 353.458
Monoisotopic: 353.210327123
Chemical Formula
C21H27N3O2
InChI Key
KPJZHOPZRAFDTN-NQUBZZJWSA-N
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
IUPAC Name
(4R,7R)-N-(1-hydroxybutan-2-yl)-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide
SMILES
[H][[email protected]@]12CC3=CN(C)C4=C3C(=CC=C4)C1=C[[email protected]](CN2C)C(=O)NC(CC)CO

Pharmacology

Indication

For the treatment of vascular headache

Structured Indications
Not Available
Pharmacodynamics

Methysergide has been shown, in vitro and in vivo, to inhibit or block the effects of serotonin, a substance which may be involved in the mechanism of vascular headaches. Serotonin has been variously described as a central neurohumoral agent or chemical mediator, as a "headache substance" acting directly or indirectly to lower pain threshold, as an intrinsic "motor hormone" of the gastrointestinal tract, and as a "hormone" involved in connective tissue reparative processes.

Mechanism of action

Methysergide is serotonin antagonists acts on central nervous system (CNS), which directly stimulates the smooth muscle leading to vasoconstriction. Some alpha-adrenergic blocking activity has been reported. Suggestions have been made by investigators as to the mechanism whereby Methysergide produces its clinical effects, but this has not been finally established, although it may be related to the antiserotonin effect.

TargetActionsOrganism
A5-hydroxytryptamine receptor 2B
antagonist
Human
A5-hydroxytryptamine receptor 2C
antagonist
Human
A5-hydroxytryptamine receptor 2A
antagonist
Human
A5-hydroxytryptamine receptor 1A
agonist
Human
A5-hydroxytryptamine receptor 7
antagonist
Human
U5-hydroxytryptamine receptor 1B
binder
Human
U5-hydroxytryptamine receptor 1F
binder
Human
U5-hydroxytryptamine receptor 1E
binder
Human
Absorption

Rapid

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Few cases of acute methysergide intoxication have been reported. The possible symptom complex is therefore not fully known. The following symptoms are based on these few case reports. Euphoria, hyperactivity, tachycardia, dilated pupils, and dizziness have been reported in a child with a dose of 20-24 mg of methysergide. In adults, peripheral vasospasm, with diminished or absent pulses, coldness, mottling and cyanosis, has been observed at a dose of 200 mg. Ischemic tissue damage has not been reported in acute overdosage with methysergide.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetaminophenThe risk or severity of adverse effects can be increased when Methysergide is combined with Acetaminophen.Approved
AcetazolamideThe risk or severity of adverse effects can be increased when Methysergide is combined with Acetazolamide.Approved, Vet Approved
AldesleukinThe risk or severity of adverse effects can be increased when Methysergide is combined with Aldesleukin.Approved
AlprazolamThe risk or severity of adverse effects can be increased when Methysergide is combined with Alprazolam.Approved, Illicit, Investigational
AmbroxolThe risk or severity of adverse effects can be increased when Methysergide is combined with Ambroxol.Approved
AmlodipineThe risk or severity of adverse effects can be increased when Methysergide is combined with Amlodipine.Approved
AmprenavirThe risk or severity of adverse effects can be increased when Methysergide is combined with Amprenavir.Approved
AnastrozoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Anastrozole.Approved, Investigational
AntipyrineThe risk or severity of adverse effects can be increased when Methysergide is combined with Antipyrine.Approved
Arsenic trioxideThe risk or severity of adverse effects can be increased when Methysergide is combined with Arsenic trioxide.Approved, Investigational
AstemizoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Astemizole.Approved, Withdrawn
AtazanavirThe risk or severity of adverse effects can be increased when Methysergide is combined with Atazanavir.Approved, Investigational
AtomoxetineThe risk or severity of adverse effects can be increased when Methysergide is combined with Atomoxetine.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Methysergide is combined with Atorvastatin.Approved
AzelastineThe risk or severity of adverse effects can be increased when Methysergide is combined with Azelastine.Approved
AzithromycinThe risk or severity of adverse effects can be increased when Methysergide is combined with Azithromycin.Approved
BetamethasoneThe risk or severity of adverse effects can be increased when Methysergide is combined with Betamethasone.Approved, Vet Approved
BicalutamideThe risk or severity of adverse effects can be increased when Methysergide is combined with Bicalutamide.Approved
BifonazoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Bifonazole.Approved
BoceprevirThe risk or severity of adverse effects can be increased when Methysergide is combined with Boceprevir.Withdrawn
BortezomibThe risk or severity of adverse effects can be increased when Methysergide is combined with Bortezomib.Approved, Investigational
Brentuximab vedotinThe risk or severity of adverse effects can be increased when Methysergide is combined with Brentuximab vedotin.Approved
BromocriptineThe risk or severity of adverse effects can be increased when Methysergide is combined with Bromocriptine.Approved, Investigational
BuprenorphineThe risk or severity of adverse effects can be increased when Methysergide is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
CabergolineThe risk or severity of adverse effects can be increased when Methysergide is combined with Cabergoline.Approved
CaffeineThe risk or severity of adverse effects can be increased when Methysergide is combined with Caffeine.Approved
CapsaicinThe risk or severity of adverse effects can be increased when Methysergide is combined with Capsaicin.Approved
CaspofunginThe risk or severity of adverse effects can be increased when Methysergide is combined with Caspofungin.Approved
CeritinibThe risk or severity of adverse effects can be increased when Methysergide is combined with Ceritinib.Approved
CerivastatinThe risk or severity of adverse effects can be increased when Methysergide is combined with Cerivastatin.Withdrawn
ChloramphenicolThe risk or severity of adverse effects can be increased when Methysergide is combined with Chloramphenicol.Approved, Vet Approved
ChlorzoxazoneThe risk or severity of adverse effects can be increased when Methysergide is combined with Chlorzoxazone.Approved
CilostazolThe risk or severity of adverse effects can be increased when Methysergide is combined with Cilostazol.Approved
CiprofloxacinThe risk or severity of adverse effects can be increased when Methysergide is combined with Ciprofloxacin.Approved, Investigational
CisaprideThe risk or severity of adverse effects can be increased when Methysergide is combined with Cisapride.Approved, Investigational, Withdrawn
ClarithromycinThe risk or severity of adverse effects can be increased when Methysergide is combined with Clarithromycin.Approved
ClemastineThe risk or severity of adverse effects can be increased when Methysergide is combined with Clemastine.Approved
ClindamycinThe risk or severity of adverse effects can be increased when Methysergide is combined with Clindamycin.Approved, Vet Approved
ClofazimineThe risk or severity of adverse effects can be increased when Methysergide is combined with Clofazimine.Approved, Investigational
ClomifeneThe risk or severity of adverse effects can be increased when Methysergide is combined with Clomifene.Approved, Investigational
ClotiazepamThe risk or severity of adverse effects can be increased when Methysergide is combined with Clotiazepam.Approved, Illicit
ClotrimazoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Clotrimazole.Approved, Vet Approved
ClozapineThe risk or severity of adverse effects can be increased when Methysergide is combined with Clozapine.Approved
CobicistatThe risk or severity of adverse effects can be increased when Methysergide is combined with Cobicistat.Approved
CocaineThe risk or severity of adverse effects can be increased when Methysergide is combined with Cocaine.Approved, Illicit
ColchicineThe risk or severity of adverse effects can be increased when Methysergide is combined with Colchicine.Approved
ConivaptanThe risk or severity of adverse effects can be increased when Methysergide is combined with Conivaptan.Approved, Investigational
Cortisone acetateThe risk or severity of adverse effects can be increased when Methysergide is combined with Cortisone acetate.Approved
CrizotinibThe risk or severity of adverse effects can be increased when Methysergide is combined with Crizotinib.Approved
CyclophosphamideThe risk or severity of adverse effects can be increased when Methysergide is combined with Cyclophosphamide.Approved, Investigational
CyclosporineThe risk or severity of adverse effects can be increased when Methysergide is combined with Cyclosporine.Approved, Investigational, Vet Approved
DalfopristinThe risk or severity of adverse effects can be increased when Methysergide is combined with Dalfopristin.Approved
DanazolThe risk or severity of adverse effects can be increased when Methysergide is combined with Danazol.Approved
DarunavirThe risk or severity of adverse effects can be increased when Methysergide is combined with Darunavir.Approved
DasatinibThe risk or severity of adverse effects can be increased when Methysergide is combined with Dasatinib.Approved, Investigational
DaunorubicinThe risk or severity of adverse effects can be increased when Methysergide is combined with Daunorubicin.Approved
DelavirdineThe risk or severity of adverse effects can be increased when Methysergide is combined with Delavirdine.Approved
DesipramineThe risk or severity of adverse effects can be increased when Methysergide is combined with Desipramine.Approved
DexamethasoneThe risk or severity of adverse effects can be increased when Methysergide is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextropropoxypheneThe risk or severity of adverse effects can be increased when Methysergide is combined with Dextropropoxyphene.Approved, Illicit, Withdrawn
DiazepamThe risk or severity of adverse effects can be increased when Methysergide is combined with Diazepam.Approved, Illicit, Vet Approved
DiethylstilbestrolThe risk or severity of adverse effects can be increased when Methysergide is combined with Diethylstilbestrol.Approved
DihydroergotamineThe risk or severity of adverse effects can be increased when Methysergide is combined with Dihydroergotamine.Approved
Dimethyl sulfoxideThe risk or severity of adverse effects can be increased when Methysergide is combined with Dimethyl sulfoxide.Approved, Vet Approved
DocetaxelThe risk or severity of adverse effects can be increased when Methysergide is combined with Docetaxel.Approved, Investigational
DoxorubicinThe risk or severity of adverse effects can be increased when Methysergide is combined with Doxorubicin.Approved, Investigational
DoxycyclineThe risk or severity of adverse effects can be increased when Methysergide is combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe risk or severity of adverse effects can be increased when Methysergide is combined with Dronedarone.Approved
EconazoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Econazole.Approved
EfavirenzThe risk or severity of adverse effects can be increased when Methysergide is combined with Efavirenz.Approved, Investigational
ElbasvirThe risk or severity of adverse effects can be increased when Methysergide is combined with Elbasvir.Approved
EnasidenibThe risk or severity of adverse effects can be increased when Methysergide is combined with Enasidenib.Approved
EpinephrineThe risk or severity of adverse effects can be increased when Methysergide is combined with Epinephrine.Approved, Vet Approved
Ergoloid mesylateThe risk or severity of adverse effects can be increased when Methysergide is combined with Ergoloid mesylate.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Methysergide is combined with Ergonovine.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Methysergide is combined with Ergotamine.Approved
ErythromycinThe risk or severity of adverse effects can be increased when Methysergide is combined with Erythromycin.Approved, Vet Approved
EthanolThe risk or severity of adverse effects can be increased when Methysergide is combined with Ethanol.Approved
EtoposideThe risk or severity of adverse effects can be increased when Methysergide is combined with Etoposide.Approved
EtoricoxibThe risk or severity of adverse effects can be increased when Methysergide is combined with Etoricoxib.Approved, Investigational
EzetimibeThe risk or severity of adverse effects can be increased when Methysergide is combined with Ezetimibe.Approved
FelodipineThe risk or severity of adverse effects can be increased when Methysergide is combined with Felodipine.Approved, Investigational
FentanylThe risk or severity of adverse effects can be increased when Methysergide is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FluoxetineThe risk or severity of adverse effects can be increased when Methysergide is combined with Fluoxetine.Approved, Vet Approved
Fluticasone propionateThe risk or severity of adverse effects can be increased when Methysergide is combined with Fluticasone propionate.Approved
FluvastatinThe risk or severity of adverse effects can be increased when Methysergide is combined with Fluvastatin.Approved
FluvoxamineThe risk or severity of adverse effects can be increased when Methysergide is combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe risk or severity of adverse effects can be increased when Methysergide is combined with Fosamprenavir.Approved
FosaprepitantThe risk or severity of adverse effects can be increased when Methysergide is combined with Fosaprepitant.Approved
GemfibrozilThe risk or severity of adverse effects can be increased when Methysergide is combined with Gemfibrozil.Approved
GlyburideThe risk or severity of adverse effects can be increased when Methysergide is combined with Glyburide.Approved
Glycerol PhenylbutyrateThe risk or severity of adverse effects can be increased when Methysergide is combined with Glycerol Phenylbutyrate.Approved
HaloperidolThe risk or severity of adverse effects can be increased when Methysergide is combined with Haloperidol.Approved
HistamineThe risk or severity of adverse effects can be increased when Methysergide is combined with Histamine.Approved, Investigational
HydralazineThe risk or severity of adverse effects can be increased when Methysergide is combined with Hydralazine.Approved
HydrocortisoneThe risk or severity of adverse effects can be increased when Methysergide is combined with Hydrocortisone.Approved, Vet Approved
IdelalisibThe risk or severity of adverse effects can be increased when Methysergide is combined with Idelalisib.Approved
IfosfamideThe risk or severity of adverse effects can be increased when Methysergide is combined with Ifosfamide.Approved
IloperidoneThe risk or severity of adverse effects can be increased when Methysergide is combined with Iloperidone.Approved
ImatinibThe risk or severity of adverse effects can be increased when Methysergide is combined with Imatinib.Approved
IndinavirThe risk or severity of adverse effects can be increased when Methysergide is combined with Indinavir.Approved
indisulamThe risk or severity of adverse effects can be increased when Methysergide is combined with indisulam.Investigational
IrbesartanThe risk or severity of adverse effects can be increased when Methysergide is combined with Irbesartan.Approved, Investigational
IrinotecanThe risk or severity of adverse effects can be increased when Methysergide is combined with Irinotecan.Approved, Investigational
IsavuconazoniumThe risk or severity of adverse effects can be increased when Methysergide is combined with Isavuconazonium.Approved, Investigational
IsoniazidThe risk or severity of adverse effects can be increased when Methysergide is combined with Isoniazid.Approved
IsradipineThe risk or severity of adverse effects can be increased when Methysergide is combined with Isradipine.Approved
ItraconazoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Itraconazole.Approved, Investigational
IvacaftorThe risk or severity of adverse effects can be increased when Methysergide is combined with Ivacaftor.Approved
JosamycinThe risk or severity of adverse effects can be increased when Methysergide is combined with Josamycin.Approved
KetazolamThe risk or severity of adverse effects can be increased when Methysergide is combined with Ketazolam.Approved
KetoconazoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Ketoconazole.Approved, Investigational
LansoprazoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Lansoprazole.Approved, Investigational
LapatinibThe risk or severity of adverse effects can be increased when Methysergide is combined with Lapatinib.Approved, Investigational
LercanidipineThe risk or severity of adverse effects can be increased when Methysergide is combined with Lercanidipine.Approved, Investigational
LevofloxacinThe risk or severity of adverse effects can be increased when Methysergide is combined with Levofloxacin.Approved, Investigational
LevosalbutamolThe risk or severity of adverse effects can be increased when Methysergide is combined with Levosalbutamol.Approved
LidocaineThe risk or severity of adverse effects can be increased when Methysergide is combined with Lidocaine.Approved, Vet Approved
LinagliptinThe risk or severity of adverse effects can be increased when Methysergide is combined with Linagliptin.Approved
LomitapideThe risk or severity of adverse effects can be increased when Methysergide is combined with Lomitapide.Approved
LomustineThe risk or severity of adverse effects can be increased when Methysergide is combined with Lomustine.Approved
LopinavirThe risk or severity of adverse effects can be increased when Methysergide is combined with Lopinavir.Approved
LoratadineThe risk or severity of adverse effects can be increased when Methysergide is combined with Loratadine.Approved
LosartanThe risk or severity of adverse effects can be increased when Methysergide is combined with Losartan.Approved
LovastatinThe risk or severity of adverse effects can be increased when Methysergide is combined with Lovastatin.Approved, Investigational
LuliconazoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Luliconazole.Approved
LurasidoneThe risk or severity of adverse effects can be increased when Methysergide is combined with Lurasidone.Approved
ManidipineThe risk or severity of adverse effects can be increased when Methysergide is combined with Manidipine.Approved
MefloquineThe risk or severity of adverse effects can be increased when Methysergide is combined with Mefloquine.Approved
MequitazineThe risk or severity of adverse effects can be increased when Methysergide is combined with Mequitazine.Approved
MethadoneThe risk or severity of adverse effects can be increased when Methysergide is combined with Methadone.Approved
MethazolamideThe risk or severity of adverse effects can be increased when Methysergide is combined with Methazolamide.Approved
MethimazoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Methimazole.Approved
MethylergometrineThe risk or severity of adverse effects can be increased when Methysergide is combined with Methylergometrine.Approved
MethylprednisoloneThe risk or severity of adverse effects can be increased when Methysergide is combined with Methylprednisolone.Approved, Vet Approved
MetronidazoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Metronidazole.Approved
MetyraponeThe risk or severity of adverse effects can be increased when Methysergide is combined with Metyrapone.Approved
MibefradilThe risk or severity of adverse effects can be increased when Methysergide is combined with Mibefradil.Withdrawn
MiconazoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Miconazole.Approved, Investigational, Vet Approved
MidazolamThe risk or severity of adverse effects can be increased when Methysergide is combined with Midazolam.Approved, Illicit
MifepristoneThe risk or severity of adverse effects can be increased when Methysergide is combined with Mifepristone.Approved, Investigational
MirtazapineThe risk or severity of adverse effects can be increased when Methysergide is combined with Mirtazapine.Approved
MitoxantroneThe risk or severity of adverse effects can be increased when Methysergide is combined with Mitoxantrone.Approved, Investigational
ModafinilThe risk or severity of adverse effects can be increased when Methysergide is combined with Modafinil.Approved, Investigational
NelfinavirThe risk or severity of adverse effects can be increased when Methysergide is combined with Nelfinavir.Approved
NetupitantThe risk or severity of adverse effects can be increased when Methysergide is combined with Netupitant.Approved
NevirapineThe risk or severity of adverse effects can be increased when Methysergide is combined with Nevirapine.Approved
NicardipineThe risk or severity of adverse effects can be increased when Methysergide is combined with Nicardipine.Approved
NicotinamideThe risk or severity of adverse effects can be increased when Methysergide is combined with Nicotinamide.Approved
NifedipineThe risk or severity of adverse effects can be increased when Methysergide is combined with Nifedipine.Approved
NilotinibThe risk or severity of adverse effects can be increased when Methysergide is combined with Nilotinib.Approved, Investigational
NilvadipineThe risk or severity of adverse effects can be increased when Methysergide is combined with Nilvadipine.Approved
NisoldipineThe risk or severity of adverse effects can be increased when Methysergide is combined with Nisoldipine.Approved
NitrendipineThe risk or severity of adverse effects can be increased when Methysergide is combined with Nitrendipine.Approved
Nitric OxideThe risk or severity of adverse effects can be increased when Methysergide is combined with Nitric Oxide.Approved
NorfloxacinThe risk or severity of adverse effects can be increased when Methysergide is combined with Norfloxacin.Approved
NoscapineThe risk or severity of adverse effects can be increased when Methysergide is combined with Noscapine.Investigational
OlanzapineThe risk or severity of adverse effects can be increased when Methysergide is combined with Olanzapine.Approved, Investigational
OlaparibThe risk or severity of adverse effects can be increased when Methysergide is combined with Olaparib.Approved
OmeprazoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Omeprazole.Approved, Investigational, Vet Approved
OxybutyninThe risk or severity of adverse effects can be increased when Methysergide is combined with Oxybutynin.Approved, Investigational
OxymetholoneThe risk or severity of adverse effects can be increased when Methysergide is combined with Oxymetholone.Approved, Illicit
PaclitaxelThe risk or severity of adverse effects can be increased when Methysergide is combined with Paclitaxel.Approved, Vet Approved
PalbociclibThe risk or severity of adverse effects can be increased when Methysergide is combined with Palbociclib.Approved
ParamethasoneThe risk or severity of adverse effects can be increased when Methysergide is combined with Paramethasone.Approved
PazopanibThe risk or severity of adverse effects can be increased when Methysergide is combined with Pazopanib.Approved
PergolideThe risk or severity of adverse effects can be increased when Methysergide is combined with Pergolide.Approved, Vet Approved, Withdrawn
PhenelzineThe risk or severity of adverse effects can be increased when Methysergide is combined with Phenelzine.Approved
PilocarpineThe risk or severity of adverse effects can be increased when Methysergide is combined with Pilocarpine.Approved
PimozideThe risk or severity of adverse effects can be increased when Methysergide is combined with Pimozide.Approved
PosaconazoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe risk or severity of adverse effects can be increased when Methysergide is combined with Pravastatin.Approved
PrednisoloneThe risk or severity of adverse effects can be increased when Methysergide is combined with Prednisolone.Approved, Vet Approved
PrednisoneThe risk or severity of adverse effects can be increased when Methysergide is combined with Prednisone.Approved, Vet Approved
PrimaquineThe risk or severity of adverse effects can be increased when Methysergide is combined with Primaquine.Approved
ProgesteroneThe risk or severity of adverse effects can be increased when Methysergide is combined with Progesterone.Approved, Vet Approved
PropofolThe risk or severity of adverse effects can be increased when Methysergide is combined with Propofol.Approved, Investigational, Vet Approved
QuinidineThe risk or severity of adverse effects can be increased when Methysergide is combined with Quinidine.Approved
QuinineThe risk or severity of adverse effects can be increased when Methysergide is combined with Quinine.Approved
QuinupristinThe risk or severity of adverse effects can be increased when Methysergide is combined with Quinupristin.Approved
RabeprazoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Rabeprazole.Approved, Investigational
RaloxifeneThe risk or severity of adverse effects can be increased when Methysergide is combined with Raloxifene.Approved, Investigational
RanitidineThe risk or severity of adverse effects can be increased when Methysergide is combined with Ranitidine.Approved
RanolazineThe risk or severity of adverse effects can be increased when Methysergide is combined with Ranolazine.Approved, Investigational
RegorafenibThe risk or severity of adverse effects can be increased when Methysergide is combined with Regorafenib.Approved
RepaglinideThe risk or severity of adverse effects can be increased when Methysergide is combined with Repaglinide.Approved, Investigational
ResveratrolThe risk or severity of adverse effects can be increased when Methysergide is combined with Resveratrol.Experimental, Investigational
RilpivirineThe risk or severity of adverse effects can be increased when Methysergide is combined with Rilpivirine.Approved
RisperidoneThe risk or severity of adverse effects can be increased when Methysergide is combined with Risperidone.Approved, Investigational
RitonavirThe risk or severity of adverse effects can be increased when Methysergide is combined with Ritonavir.Approved, Investigational
RivastigmineThe risk or severity of adverse effects can be increased when Methysergide is combined with Rivastigmine.Approved, Investigational
RolitetracyclineThe risk or severity of adverse effects can be increased when Methysergide is combined with Rolitetracycline.Approved
RosuvastatinThe risk or severity of adverse effects can be increased when Methysergide is combined with Rosuvastatin.Approved
RoxithromycinThe risk or severity of adverse effects can be increased when Methysergide is combined with Roxithromycin.Approved, Withdrawn
RutinThe risk or severity of adverse effects can be increased when Methysergide is combined with Rutin.Experimental
SalbutamolThe risk or severity of adverse effects can be increased when Methysergide is combined with Salbutamol.Approved, Vet Approved
SaquinavirThe risk or severity of adverse effects can be increased when Methysergide is combined with Saquinavir.Approved, Investigational
SarilumabThe risk or severity of adverse effects can be increased when Methysergide is combined with Sarilumab.Approved
SertralineThe risk or severity of adverse effects can be increased when Methysergide is combined with Sertraline.Approved
SildenafilThe risk or severity of adverse effects can be increased when Methysergide is combined with Sildenafil.Approved, Investigational
SimeprevirThe risk or severity of adverse effects can be increased when Methysergide is combined with Simeprevir.Approved
SimvastatinThe risk or severity of adverse effects can be increased when Methysergide is combined with Simvastatin.Approved
SirolimusThe risk or severity of adverse effects can be increased when Methysergide is combined with Sirolimus.Approved, Investigational
SitaxentanThe risk or severity of adverse effects can be increased when Methysergide is combined with Sitaxentan.Approved, Investigational, Withdrawn
SorafenibThe risk or severity of adverse effects can be increased when Methysergide is combined with Sorafenib.Approved, Investigational
StiripentolThe risk or severity of adverse effects can be increased when Methysergide is combined with Stiripentol.Approved
SulfamethoxazoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Sulfamethoxazole.Approved
SulfanilamideThe risk or severity of adverse effects can be increased when Methysergide is combined with Sulfanilamide.Approved
SulfinpyrazoneThe risk or severity of adverse effects can be increased when Methysergide is combined with Sulfinpyrazone.Approved
SulfisoxazoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Sulfisoxazole.Approved, Vet Approved
TacrolimusThe risk or severity of adverse effects can be increased when Methysergide is combined with Tacrolimus.Approved, Investigational
TadalafilThe risk or severity of adverse effects can be increased when Methysergide is combined with Tadalafil.Approved, Investigational
TamoxifenThe risk or severity of adverse effects can be increased when Methysergide is combined with Tamoxifen.Approved
TelaprevirThe risk or severity of adverse effects can be increased when Methysergide is combined with Telaprevir.Withdrawn
TelithromycinThe risk or severity of adverse effects can be increased when Methysergide is combined with Telithromycin.Approved
TemsirolimusThe risk or severity of adverse effects can be increased when Methysergide is combined with Temsirolimus.Approved
TeniposideThe risk or severity of adverse effects can be increased when Methysergide is combined with Teniposide.Approved
TerfenadineThe risk or severity of adverse effects can be increased when Methysergide is combined with Terfenadine.Withdrawn
TesmilifeneThe risk or severity of adverse effects can be increased when Methysergide is combined with Tesmilifene.Investigational
TestosteroneThe risk or severity of adverse effects can be increased when Methysergide is combined with Testosterone.Approved, Investigational
TetracyclineThe risk or severity of adverse effects can be increased when Methysergide is combined with Tetracycline.Approved, Vet Approved
ThiopentalThe risk or severity of adverse effects can be increased when Methysergide is combined with Thiopental.Approved, Vet Approved
TicagrelorThe risk or severity of adverse effects can be increased when Methysergide is combined with Ticagrelor.Approved
TiclopidineThe risk or severity of adverse effects can be increased when Methysergide is combined with Ticlopidine.Approved
TioconazoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Tioconazole.Approved
TipranavirThe risk or severity of adverse effects can be increased when Methysergide is combined with Tipranavir.Approved, Investigational
TofisopamThe risk or severity of adverse effects can be increased when Methysergide is combined with Tofisopam.Approved
TopiroxostatThe risk or severity of adverse effects can be increased when Methysergide is combined with Topiroxostat.Approved
TopotecanThe risk or severity of adverse effects can be increased when Methysergide is combined with Topotecan.Approved, Investigational
TramadolThe risk or severity of adverse effects can be increased when Methysergide is combined with Tramadol.Approved, Investigational
TranylcypromineThe risk or severity of adverse effects can be increased when Methysergide is combined with Tranylcypromine.Approved
TroglitazoneThe risk or severity of adverse effects can be increased when Methysergide is combined with Troglitazone.Withdrawn
TroleandomycinThe risk or severity of adverse effects can be increased when Methysergide is combined with Troleandomycin.Approved
Valproic AcidThe risk or severity of adverse effects can be increased when Methysergide is combined with Valproic Acid.Approved, Investigational
VenlafaxineThe risk or severity of adverse effects can be increased when Methysergide is combined with Venlafaxine.Approved
VinblastineThe risk or severity of adverse effects can be increased when Methysergide is combined with Vinblastine.Approved
VincristineThe risk or severity of adverse effects can be increased when Methysergide is combined with Vincristine.Approved, Investigational
VinorelbineThe risk or severity of adverse effects can be increased when Methysergide is combined with Vinorelbine.Approved, Investigational
VoriconazoleThe risk or severity of adverse effects can be increased when Methysergide is combined with Voriconazole.Approved, Investigational
ZafirlukastThe risk or severity of adverse effects can be increased when Methysergide is combined with Zafirlukast.Approved, Investigational
ZiprasidoneThe risk or severity of adverse effects can be increased when Methysergide is combined with Ziprasidone.Approved
ZucapsaicinThe risk or severity of adverse effects can be increased when Methysergide is combined with Zucapsaicin.Approved
Food Interactions
  • Take with food to reduce irritation.

References

General References
Not Available
External Links
Human Metabolome Database
HMDB14392
KEGG Drug
D02357
KEGG Compound
C07199
PubChem Compound
6540428
PubChem Substance
46506117
ChemSpider
5022813
BindingDB
50031942
ChEBI
584020
ChEMBL
CHEMBL1065
Therapeutic Targets Database
DAP000366
PharmGKB
PA164743265
IUPHAR
134
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Wikipedia
Methysergide
ATC Codes
N02CA04 — Methysergide

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Novartis pharmaceuticals corp
Packagers
  • Novartis AG
  • Pharmaceutical Utilization Management Program VA Inc.
  • Professional Co.
Dosage forms
FormRouteStrength
TabletOral2 mg
Prices
Unit descriptionCostUnit
Methysergide maleate 100% powder2580.0USD g
Desyrel 100 mg tablet4.26USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)195 °CPhysProp
logP1.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.224 mg/mLALOGPS
logP2.22ALOGPS
logP1.82ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)15.01ChemAxon
pKa (Strongest Basic)7.85ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.5 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity104.47 m3·mol-1ChemAxon
Polarizability40.41 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.7015
Caco-2 permeable-0.8064
P-glycoprotein substrateSubstrate0.8396
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.7515
Renal organic cation transporterNon-inhibitor0.8129
CYP450 2C9 substrateNon-substrate0.8536
CYP450 2D6 substrateNon-substrate0.8474
CYP450 3A4 substrateSubstrate0.6889
CYP450 1A2 substrateNon-inhibitor0.791
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.8867
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9161
Ames testNon AMES toxic0.5241
CarcinogenicityNon-carcinogens0.8906
BiodegradationNot ready biodegradable0.8144
Rat acute toxicity3.3039 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9569
hERG inhibition (predictor II)Inhibitor0.6274
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as lysergamides. These are amides of Lysergic acids.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Ergoline and derivatives
Sub Class
Lysergic acids and derivatives
Direct Parent
Lysergamides
Alternative Parents
Indoloquinolines / Benzoquinolines / Quinoline-3-carboxamides / Pyrroloquinolines / 3-alkylindoles / N-alkylindoles / Isoindoles and derivatives / Aralkylamines / N-methylpyrroles / Benzenoids
show 10 more
Substituents
Lysergic acid amide / Indoloquinoline / Benzoquinoline / Pyrroloquinoline / Quinoline-3-carboxamide / N-alkylindole / Quinoline / 3-alkylindole / Indole / Indole or derivatives
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monocarboxylic acid amide, ergot alkaloid (CHEBI:584020)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various ergot alkaloid derivatives and psychoactive substances. Ligand binding causes a conformation...
Gene Name
HTR2B
Uniprot ID
P41595
Uniprot Name
5-hydroxytryptamine receptor 2B
Molecular Weight
54297.41 Da
References
  1. Schmuck K, Ullmer C, Kalkman HO, Probst A, Lubbert H: Activation of meningeal 5-HT2B receptors: an early step in the generation of migraine headache? Eur J Neurosci. 1996 May;8(5):959-67. [PubMed:8743744]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
Gene Name
HTR2C
Uniprot ID
P28335
Uniprot Name
5-hydroxytryptamine receptor 2C
Molecular Weight
51820.705 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Johnson MP, Lea RA, Curtain RP, MacMillan JC, Griffiths LR: An investigation of the 5-HT2C receptor gene as a migraine candidate gene. Am J Med Genet B Neuropsychiatr Genet. 2003 Feb;117B(1):86-9. [PubMed:12555241]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Castilho VM, Avanzi V, Brandao ML: Antinociception elicited by aversive stimulation of the inferior colliculus. Pharmacol Biochem Behav. 1999 Mar;62(3):425-31. [PubMed:10080233]
  2. Geerts IS, Matthys KE, Herman AG, Bult H: Involvement of 5-HT1B receptors in collar-induced hypersensitivity to 5-hydroxytryptamine of the rabbit carotid artery. Br J Pharmacol. 1999 Jul;127(6):1327-36. [PubMed:10455282]
  3. Shaw AM, Brown C, Irvine J, Bunton DC, MacDonald A: Role of the 5-HT(2A)receptor and alpha(1)-adrenoceptor in the contractile response of rat pulmonary artery to 5-HT in the presence and absence of nitric oxide. Pulm Pharmacol Ther. 2000;13(6):277-85. [PubMed:11061982]
  4. Prins NH, Akkermans LM, Lefebvre RA, Schuurkes JA: Characterization of the receptors involved in the 5-HT-induced excitation of canine antral longitudinal muscle. Br J Pharmacol. 2001 Nov;134(6):1351-9. [PubMed:11704657]
  5. Connor JD, Rasheed H, Gilani AH, Cheema M, Rizvi Z, Saeed SA: Second messengers in platelet aggregation evoked by serotonin and A23187, a calcium ionophore. Life Sci. 2001 Oct 26;69(23):2759-64. [PubMed:11720080]
  6. Robert A. Davidoff (2002). Migraine : Manifestations, Pathogenesis, and Management (pp. 438). Oxford University Press. [ISBN:0198031351]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name
HTR1A
Uniprot ID
P08908
Uniprot Name
5-hydroxytryptamine receptor 1A
Molecular Weight
46106.335 Da
References
  1. Scrogin KE, Johnson AK, Brooks VL: Methysergide delays the decompensatory responses to severe hemorrhage by activating 5-HT(1A) receptors. Am J Physiol Regul Integr Comp Physiol. 2000 Nov;279(5):R1776-86. [PubMed:11049861]
  2. Sugimoto Y, Inoue K, Yamada J: The tricyclic antidepressant clomipramine increases plasma glucose levels of mice. J Pharmacol Sci. 2003 Sep;93(1):74-9. [PubMed:14501155]
  3. Sugimoto Y, Inoue K, Yamada J: Involvement of 5-HT(2) receptor in imipramine-induced hyperglycemia in mice. Horm Metab Res. 2003 Sep;35(9):511-6. [PubMed:14517765]
  4. Skyba DA, Radhakrishnan R, Rohlwing JJ, Wright A, Sluka KA: Joint manipulation reduces hyperalgesia by activation of monoamine receptors but not opioid or GABA receptors in the spinal cord. Pain. 2003 Nov;106(1-2):159-68. [PubMed:14581123]
  5. Pranzatelli MR, Balletti J: Characterization of 5-hydroxytryptamine 1A-like binding sites in human ganglioneuroblastoma. Neurosci Lett. 1991 Oct 28;132(1):117-20. [PubMed:1838579]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Antagonist
General Function
Serotonin receptor activity
Specific Function
This is one of the several different receptors for 5-hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor ...
Gene Name
HTR7
Uniprot ID
P34969
Uniprot Name
5-hydroxytryptamine receptor 7
Molecular Weight
53554.43 Da
References
  1. Sugimoto Y, Inoue K, Yamada J: The tricyclic antidepressant clomipramine increases plasma glucose levels of mice. J Pharmacol Sci. 2003 Sep;93(1):74-9. [PubMed:14501155]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name
HTR1B
Uniprot ID
P28222
Uniprot Name
5-hydroxytryptamine receptor 1B
Molecular Weight
43567.535 Da
References
  1. Matsumoto I, Combs MR, Jones DJ: Characterization of 5-hydroxytryptamine1B receptors in rat spinal cord via [125I]iodocyanopindolol binding and inhibition of [3H]-5-hydroxytryptamine release. J Pharmacol Exp Ther. 1992 Feb;260(2):614-26. [PubMed:1738111]
  2. Saxena PR, Tfel-Hansen P (2005). Triptans, 5-HT 1B/1D receptor agonists in the acute treatment of migraines. In Headaches (3rd ed., pp. 469-503, 459-467). Lippincott Williams & Wilkins. [ISBN:978-0781754002]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various alkaloids and psychoactive substances. Ligand binding causes a conformation change that trig...
Gene Name
HTR1F
Uniprot ID
P30939
Uniprot Name
5-hydroxytryptamine receptor 1F
Molecular Weight
41708.505 Da
References
  1. Adham N, Kao HT, Schecter LE, Bard J, Olsen M, Urquhart D, Durkin M, Hartig PR, Weinshank RL, Branchek TA: Cloning of another human serotonin receptor (5-HT1F): a fifth 5-HT1 receptor subtype coupled to the inhibition of adenylate cyclase. Proc Natl Acad Sci U S A. 1993 Jan 15;90(2):408-12. [PubMed:8380639]
  2. Saxena PR, Tfel-Hansen P (2005). Triptans, 5-HT 1B/1D receptor agonists in the acute treatment of migraines. In Headaches (3rd ed., pp. 469-503, 459-467). Lippincott Williams & Wilkins. [ISBN:978-0781754002]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binder
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various alkaloids and psychoactive substances. Ligand binding causes a conformation change that trig...
Gene Name
HTR1E
Uniprot ID
P28566
Uniprot Name
5-hydroxytryptamine receptor 1E
Molecular Weight
41681.57 Da
References
  1. Adham N, Kao HT, Schecter LE, Bard J, Olsen M, Urquhart D, Durkin M, Hartig PR, Weinshank RL, Branchek TA: Cloning of another human serotonin receptor (5-HT1F): a fifth 5-HT1 receptor subtype coupled to the inhibition of adenylate cyclase. Proc Natl Acad Sci U S A. 1993 Jan 15;90(2):408-12. [PubMed:8380639]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:33