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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H27N3O2.C4H4O4
Molecular Weight 469.5301
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of METHYSERGIDE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CC[C@@H](CO)NC(=O)[C@H]1CN(C)[C@@H]2CC3=CN(C)C4=C3C(=CC=C4)C2=C1

InChI

InChIKey=LWYXFDXUMVEZKS-ZVFOLQIPSA-N
InChI=1S/C21H27N3O2.C4H4O4/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;5-3(6)1-2-4(7)8/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26);1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,15+,19-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C21H27N3O2
Molecular Weight 353.458
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Methysergide is an oral, synthetic ergot alkaloid, structurally related to the oxytocic agent methylergonovine and to the potent hallucinogen LSD. Methysergide is used prophylactically to reduce the frequency and intensity of severe vascular headaches. Although methysergide is an ergot alkaloid, it is a weak vasoconstrictor and oxytocic. Methysergide is a more potent antagonist of peripheral serotonin receptors than other ergot alkaloids. Methysergide is not just a 5HT2 antagonist, it is also a 5HT1 agonist. Although methysergide and sumatriptan both stimulate serotonin receptors centrally, methysergide is intended for prophylaxis while sumatriptan is indicated for treatment of an acute attack. Methysergide was approved by the FDA in 1962. Methysergide was formerly used for prophylaxis of cluster headaches/migraine headaches, but is no longer recommended due to retroperitoneal/retropulmonary fibrosis.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Aortic obstruction associated with methysergide maleate therapy for headaches.
1966 Nov 21
Retroperitoneal fibrosis secondary to methysergide bimaleate.
1967 May 27
Methysergide in mania.
1969 Feb 22
Cardiac murmurs and endocardial fibrosis associated with methysergide therapy.
1974 Nov
Methysergide in the treatment of narcolepsy.
1975 Apr
Skeletal muscle necrosis following membrane-active drugs plus serotonin.
1976 May
Methysergide-induced heart disease: a case of multivalvular and myocardial fibrosis.
1977 Nov
Migraine and systemic scleroderma.
1978 Apr
Methysergide therapy and constrictive pericarditis.
1978 Feb
Indications for surgical replacement of the mitral valve. With particular reference to common and uncommon causes of mitral regurgitation.
1979 Jul
The influence of cerebral 5-hydroxytryptamine on catalepsy induced by brain-amine depleting neuroleptics or by cholinomimetics.
1979 Oct
[Distal mesenteric arteritis: a rare complication of D. methylsergide treatment (author's transl)].
1981 Apr
Arterial complications of migraine treatment with methysergide and parenteral ergotamine.
1982 Jul 24
Effects of serotonergic and anticholinergic drugs in haloperidol-induced dystonia in Cebus monkeys.
1986
Antagonism of drug-induced yawning and penile erections in rats.
1986 Mar 18
Methysergide-induced lower extremity arterial insufficiency.
1986 Sep
St. Anthony's fire, then and now: a case report and historical review.
1987 Jul
Methysergide-induced psychosis: case report with long-term follow-up.
1989
[Isolated stenosis of the popliteal artery after treatment with methysergide. An anatomopathologic study].
1990
Chronic pain after methysergide: a new cause of ischemic monomelic neuropathy.
1991 Nov-Dec
Human serotonin 1D receptor is encoded by a subfamily of two distinct genes: 5-HT1D alpha and 5-HT1D beta.
1992 Apr 15
Molecular cloning of a serotonin receptor from human brain (5HT1E): a fifth 5HT1-like subtype.
1992 Jun 15
Profile of capsaicin-induced mouse ear oedema as neurogenic inflammatory model: comparison with arachidonic acid-induced ear oedema.
1993 Dec
A useful method for differential evaluation of anti-inflammatory effects due to cyclooxygenase and 5-lipoxygenase inhibitions in mice.
1994 Aug
Expression of functional mouse 5-HT5A serotonin receptor in the methylotrophic yeast Pichia pastoris: pharmacological characterization and localization.
1995 Dec 27
Serotonin syndrome complicating migraine pharmacotherapy.
1996 Aug
Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor.
1996 Jan
Two amino acid differences in the sixth transmembrane domain are partially responsible for the pharmacological differences between the 5-HT1D beta and 5-HT1E 5-hydroxytryptamine receptors.
1996 Nov
Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells.
1997 Apr-May
Cloning, expression and pharmacology of a truncated splice variant of the human 5-HT7 receptor (h5-HT7b).
1997 Sep
Interaction of tryptamine and ergoline compounds with threonine 196 in the ligand binding site of the 5-hydroxytryptamine6 receptor.
1997 Sep
Successful repair of aortic and mitral incompetence induced by methylsergide maleate: confirmation by intraoperative transesophageal echocardiography.
2003 Apr
Hyperalgesia induced by Asp49 and Lys49 phospholipases A2 from Bothrops asper snake venom: pharmacological mediation and molecular determinants.
2003 May
Effects of EGIS-7625, a selective and competitive 5-HT2B receptor antagonist.
2003 Sep-Nov
Serotonergic and dopaminergic influence of the duration of embryogenesis and intracapsular locomotion of Lymnaea stagnalis L.
2004
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.
2004 Aug
Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor.
2004 Jan 26
Involvement of some 5-HT receptors in methamphetamine-induced locomotor activity in mice.
2004 Jun
Severe multivalvular heart disease: a new complication of the ergot derivative dopamine agonists.
2004 Jun
Methysergide-induced retroperitoneal fibrosis and pericardial effusion.
2004 May
Binding of tryptamine analogs at h5-HT1E receptors: a structure-affinity investigation.
2004 May 15
[Neuromediatorial mechanisms of analgesia during general anesthesia].
2004 May-Jun
Evidence for a spinal serotonergic control of the peripheral inflammation in the rat.
2005 Apr 1
Methysergide-induced scleroderma-like changes of the legs.
2005 Jul
[3H]LY334370, a novel radioligand for the 5-HT1F receptor. I. In vitro characterization of binding properties.
2005 Mar
Methysergide-induced valvular heart disease: a report of 2 cases.
2006
Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat.
2006 Mar 27
Drugs and valvular heart disease.
2007 Jan 4
Characterization of the antinociceptive and anti-inflammatory activities from Cocos nucifera L. (Palmae).
2009 Apr 21
5-hydroxytryptamine modulates migration, cytokine and chemokine release and T-cell priming capacity of dendritic cells in vitro and in vivo.
2009 Jul 31
Patents

Sample Use Guides

In Vivo Use Guide
Usual adult dose 4-8 mg daily. Tablets to be given with meals
Route of Administration: Oral
In Vitro Use Guide
The actions of 5-HT were significantly reversed by the 5-HT(1/2/5/7) receptor antagonist methysergide (0.5 uM)
Substance Class Chemical
Created
by admin
on Tue Oct 22 06:08:55 UTC 2019
Edited
by admin
on Tue Oct 22 06:08:55 UTC 2019
Record UNII
2U7H1466GH
Record Status Validated (UNII)
Record Version
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Name Type Language
METHYSERGIDE MALEATE
MART.   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
METHYSERGIDE MALEATE [WHO-DD]
Common Name English
9,10-DIDEHYDRO-N-(1-(HYDROXYMETHYL)PROPYL)-1,6-DIMETHYLERGOLINE-8.BETA.-CARBOXAMIDE MALEATE (1:1) (SALT)
Common Name English
SANSERT
Brand Name English
METHYSERGIDE MALEATE [VANDF]
Common Name English
METHYSERGIDE MALEATE [USP]
Common Name English
NSC-186061
Code English
METHYSERGIDE MALEATE [USP-RS]
Common Name English
METHYSERGIDE HYDROGEN MALEATE [MI]
Common Name English
METHYSERGIDE MALEATE [ORANGE BOOK]
Common Name English
METHYSERGIDE MALEATE [MART.]
Common Name English
ERGOLINE-8-CARBOXAMIDE, 9,10-DIDEHYDRO-N-(1-(HYDROXYMETHYL)PROPYL)-1,6-DIMETHYL-, (8.BETA.)-, (Z)-2-BUTENEDIOATE (1:1) (SALT)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47795
Created by admin on Tue Oct 22 06:08:55 UTC 2019 , Edited by admin on Tue Oct 22 06:08:55 UTC 2019
Code System Code Type Description
EVMPD
SUB03263MIG
Created by admin on Tue Oct 22 06:08:55 UTC 2019 , Edited by admin on Tue Oct 22 06:08:55 UTC 2019
PRIMARY
RXCUI
203190
Created by admin on Tue Oct 22 06:08:55 UTC 2019 , Edited by admin on Tue Oct 22 06:08:55 UTC 2019
PRIMARY RxNorm
PUBCHEM
5281073
Created by admin on Tue Oct 22 06:08:55 UTC 2019 , Edited by admin on Tue Oct 22 06:08:55 UTC 2019
PRIMARY
ChEMBL
CHEMBL1065
Created by admin on Tue Oct 22 06:08:55 UTC 2019 , Edited by admin on Tue Oct 22 06:08:55 UTC 2019
PRIMARY
CAS
129-49-7
Created by admin on Tue Oct 22 06:08:55 UTC 2019 , Edited by admin on Tue Oct 22 06:08:55 UTC 2019
PRIMARY
NCI_THESAURUS
C61843
Created by admin on Tue Oct 22 06:08:55 UTC 2019 , Edited by admin on Tue Oct 22 06:08:55 UTC 2019
PRIMARY
ECHA (EC/EINECS)
204-950-9
Created by admin on Tue Oct 22 06:08:55 UTC 2019 , Edited by admin on Tue Oct 22 06:08:55 UTC 2019
PRIMARY
MERCK INDEX
M7483
Created by admin on Tue Oct 22 06:08:55 UTC 2019 , Edited by admin on Tue Oct 22 06:08:55 UTC 2019
PRIMARY Merck Index
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY