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

Similar Structures

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

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Pharmacology

Indication

For the treatment of vascular headache

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Contraindications & Blackbox Warnings

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

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

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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
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1,2-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

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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
Sansert	Tablet, coated	2 mg/1	Oral	Novartis	1962-02-12	2008-09-17

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
RxNav: 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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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	predicted	DarkChem Lite v0.1.0
[M-H]-	188.41646	predicted	DeepCCS 1.0 (2019)
[M+H]+	198.7523904	predicted	DarkChem Lite v0.1.0
[M+H]+	190.77446	predicted	DeepCCS 1.0 (2019)
[M+Na]+	198.8060904	predicted	DarkChem Lite v0.1.0
[M+Na]+	197.20827	predicted	DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.

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Details1. 5-hydroxytryptamine receptor 2B

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	6.66	N/A	N/A	A27490
Ki (nM)	1.58	N/A	N/A	A27485
Ki (nM)	0.95	N/A	N/A	A18191
Ki (nM)	4.47	N/A	N/A	A27486
Ki (nM)	2.5	N/A	N/A	A27487

Details2. 5-hydroxytryptamine receptor 2C

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	3.98	N/A	N/A	A27485 / A27486
Ki (nM)	3.31	N/A	N/A	A27484
Ki (nM)	2.45	N/A	N/A	A18191
Ki (nM)	10	N/A	N/A	A27487
Ki (nM)	1.58	N/A	N/A	A27488

Details3. 5-hydroxytryptamine receptor 2A

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	16.98	N/A	N/A	A27484

Details4. 5-hydroxytryptamine receptor 1A

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]

Details5. 5-hydroxytryptamine receptor 7

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	3.6	N/A	N/A	A27491
Ki (nM)	25.11	N/A	N/A	A27484
Ki (nM)	162.18	N/A	N/A	A27484
Ki (nM)	7.58	N/A	N/A	A27484

Details6. 5-hydroxytryptamine receptor 1B

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	33.88	N/A	N/A	A27484
Ki (nM)	34	N/A	N/A	A18238

Details7. 5-hydroxytryptamine receptor 1F

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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	228	N/A	N/A	A27489
Ki (nM)	59	N/A	N/A	A12229
Ki (nM)	229.08	N/A	N/A	A27484
Ki (nM)	323.59	N/A	N/A	A27484
Ki (nM)	218.77	N/A	N/A	A27484

Details8. 5-hydroxytryptamine receptor 1E

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

Details1. Cytochrome P450 3A4

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

Methysergide

Identification

Structure for Methysergide (DB00247)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

Targets

References

References

References

References

References

References

References

References

Enzymes

References