Methysergide
Identification
- Summary
Methysergide is an ergot alkaloid used for the prophylaxis of migraine and cluster headaches.
- Generic Name
- Methysergide
- DrugBank Accession Number
- DB00247
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 353.458
Monoisotopic: 353.210327123 - Chemical Formula
- C21H27N3O2
- Synonyms
- (+)-9,10-Didehydro-N-(1-(hydroxymethyl)propyl)-1,6-dimethylergoline-8β-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
- Méthysergide
- Methysergide
- Methysergidum
- Metisergida
- Metisergido
- N-(1-(Hydroxymethyl)propyl)-1-methyl-dextro-(+)-lysergamide
Pharmacology
- Indication
For the treatment of vascular headache
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- 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.
Target Actions Organism A5-hydroxytryptamine receptor 2B antagonistHumans A5-hydroxytryptamine receptor 2C antagonistHumans A5-hydroxytryptamine receptor 2A antagonistHumans A5-hydroxytryptamine receptor 1A agonistHumans A5-hydroxytryptamine receptor 7 antagonistHumans U5-hydroxytryptamine receptor 1B binderHumans U5-hydroxytryptamine receptor 1F binderHumans U5-hydroxytryptamine receptor 1E binderHumans - 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Methysergide is combined with 1,2-Benzodiazepine. Abametapir The serum concentration of Methysergide can be increased when it is combined with Abametapir. Abatacept The metabolism of Methysergide can be increased when combined with Abatacept. Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Methysergide. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Methysergide. - Food Interactions
- Take with food. Food reduces irritation.
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Methysergide maleate 2U7H1466GH 129-49-7 LWYXFDXUMVEZKS-ZVFOLQIPSA-N - International/Other Brands
- Deseril / Desernil
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Sansert Tablet 2 mg Oral Novartis 1962-12-31 2009-02-16 Canada Sansert Tablet, coated 2 mg/1 Oral Novartis 1962-02-12 2008-09-17 US
Categories
- ATC Codes
- N02CA04 — Methysergide
- Drug Categories
- Agents that produce hypertension
- Alkaloids
- Analgesics
- Antidepressive Agents
- Antimigraine Preparations
- Cardiovascular Agents
- Central Nervous System Depressants
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A4 Substrates (strength unknown)
- Cytochrome P-450 Substrates
- Ergolines
- Ergot Alkaloids and Derivatives
- Heterocyclic Compounds, Fused-Ring
- Lysergic Acid
- Nervous System
- Neurotransmitter Agents
- Serotonin 5-HT2 Receptor Antagonists
- Serotonin 5-HT2A Receptor Antagonists
- Serotonin 5-HT2C Receptor Antagonists
- Serotonin Agents
- Serotonin Receptor Antagonists
- Vasoconstrictor Agents
- Chemical TaxonomyProvided by Classyfire
- 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
- 3-alkylindole / Alcohol / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzoquinoline / Carbonyl group show 27 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- monocarboxylic acid amide, ergot alkaloid (CHEBI:584020)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- XZA9HY6Z98
- CAS number
- 361-37-5
- 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[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide
- SMILES
- [H][C@@]12CC3=CN(C)C4=C3C(=CC=C4)C1=C[C@H](CN2C)C(=O)NC(CC)CO
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014392
- KEGG Drug
- D02357
- KEGG Compound
- C07199
- PubChem Compound
- 6540428
- PubChem Substance
- 46506117
- ChemSpider
- 5022813
- BindingDB
- 50469883
- 6911
- ChEBI
- 584020
- ChEMBL
- CHEMBL485253
- Therapeutic Targets Database
- DAP000366
- PharmGKB
- PA164743265
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Wikipedia
- Methysergide
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Novartis pharmaceuticals corp
- Packagers
- Novartis AG
- Pharmaceutical Utilization Management Program VA Inc.
- Professional Co.
- Dosage Forms
Form Route Strength Pill Tablet Oral 2 mg Tablet, coated Oral 2 mg/1 - Prices
Unit description Cost Unit Methysergide maleate 100% powder 2580.0USD g Desyrel 100 mg tablet 4.26USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 195 °C PhysProp logP 1.5 Not Available - Predicted Properties
Property Value Source Water Solubility 0.224 mg/mL ALOGPS logP 2.22 ALOGPS logP 1.82 Chemaxon logS -3.2 ALOGPS pKa (Strongest Acidic) 15 Chemaxon pKa (Strongest Basic) 7.83 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 57.5 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 104.47 m3·mol-1 Chemaxon Polarizability 40.41 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.7015 Caco-2 permeable - 0.8064 P-glycoprotein substrate Substrate 0.8396 P-glycoprotein inhibitor I Non-inhibitor 0.8782 P-glycoprotein inhibitor II Non-inhibitor 0.7515 Renal organic cation transporter Non-inhibitor 0.8129 CYP450 2C9 substrate Non-substrate 0.8536 CYP450 2D6 substrate Non-substrate 0.8474 CYP450 3A4 substrate Substrate 0.6889 CYP450 1A2 substrate Non-inhibitor 0.791 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8931 CYP450 2C19 inhibitor Non-inhibitor 0.8867 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9161 Ames test Non AMES toxic 0.5241 Carcinogenicity Non-carcinogens 0.8906 Biodegradation Not ready biodegradable 0.8144 Rat acute toxicity 3.3039 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9569 hERG inhibition (predictor II) Inhibitor 0.6274
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-03di-4495000000-d0cc0e065ac2a249f139 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0009000000-3f8b0a51b89e695199ed Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0009000000-56f6a0ae2b06486162d2 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0f79-2169000000-921200129ebf28aa17a6 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0g4i-0029000000-1eb5849e4e37bfacfd4e Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0191000000-e43373dc398777716f13 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0bt9-7097000000-dfe71a524543c0d9f61d Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 198.6628904 predictedDarkChem Lite v0.1.0 [M-H]- 188.41646 predictedDeepCCS 1.0 (2019) [M+H]+ 198.7523904 predictedDarkChem Lite v0.1.0 [M+H]+ 190.77446 predictedDeepCCS 1.0 (2019) [M+Na]+ 198.8060904 predictedDarkChem Lite v0.1.0 [M+Na]+ 197.20827 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Castilho VM, Avanzi V, Brandao ML: Antinociception elicited by aversive stimulation of the inferior colliculus. Pharmacol Biochem Behav. 1999 Mar;62(3):425-31. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Robert A. Davidoff (2002). Migraine : Manifestations, Pathogenesis, and Management (pp. 438). Oxford University Press. [ISBN:0198031351]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Pranzatelli MR, Balletti J: Characterization of 5-hydroxytryptamine 1A-like binding sites in human ganglioneuroblastoma. Neurosci Lett. 1991 Oct 28;132(1):117-20. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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
- Humans
- 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
- 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. [Article]
- 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
- Humans
- 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
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Marcucci C., Hutchens M., Wittwer E., Weingarten T., Sprung J., Nicholson W., Lalwani K., Metro D., Dull R., Swide C., Seagull F., Kirsch J. and Sandson N. (2015). A case approach to perioperative drug-drug interactions. Springer. [ISBN:978-1-4614-7495-1]
Drug created at June 13, 2005 13:24 / Updated at January 02, 2024 23:43