Methysergide

Methysergide
Methysergide
Systematic (IUPAC) name
1-Methyl- d-lysergic acid- (1-hydroxybut- 2-yl) amide
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a603022
Pregnancy cat. X
Legal status  ?
Identifiers
CAS number 361-37-5 YesY
ATC code N02CA04
PubChem CID 9681
IUPHAR ligand 134
DrugBank APRD00463
ChemSpider 9300 YesY
UNII XZA9HY6Z98 YesY
KEGG D02357 N
ChEMBL CHEMBL1065 YesY
Chemical data
Formula C21H27N3O2 
Mol. mass 353.458 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

Methysergide (UML-491) is a prescription drug used for prophylaxis of migraine headaches and is sold under the brand names Sansert and Deseril in 2 mg dosages.

Contents

Pharmacology

Methysergide interacts with serotonin (5-HT) receptors. Its therapeutic effect in migraine prophylaxis has been associated with its antagonism at the 5-HT2B receptor.[1] Furthermore, it is an antagonist at the 5-HT2C receptor and at the 5-HT1A receptor.[2][3] It is known to have partial agonist effects on some of the other 5-HT receptors as well.[4] Methysergide is metabolised into methylergometrine in humans, which is responsible for its psychedelic effects.

Uses

Methysergide is used to treat headaches such as migraine and other recurrent throbbing headaches.[5] Methysergide is one of the most effective[6] medications for the prevention of migraine, but not for the treatment of an acute attack.

It is also used in carcinoid syndrome to treat severe diarrhea.[5]

Side effects

It has a known side effect, retroperitoneal fibrosis,[7] which is severe, although uncommon. Other severe but uncommon side effects include pleural fibrosis, and subendocardial fibrosis.

In addition, there is an increased risk of left-sided cardiac valve dysfunction.[6][8]

History

Methysergide was approved by the U.S. Food and Drug Administration (FDA) in 1962.

Novartis withdrew it from the U.S. market after taking over Sandoz, but currently lists it as a product.

Related compounds

Its molecular structure is closely related to that of LSD.

Like LSD, methysergide also produces psychedelic and hallucinogenic effects.[9]

About 4 mg is equal to 25mcg of LSD.[9]


Sandoz does not currently list this on their product guide.

See also

Triptan

References

  1. ^ Schmuck K, Ullmer C, Kalkman HO, Probst A, Lubbert H (May 1996). "Activation of meningeal 5-HT2B receptors: an early step in the generation of migraine headache?". Eur. J. Neurosci. 8 (5): 959–67. doi:10.1111/j.1460-9568.1996.tb01583.x. PMID 8743744. 
  2. ^ Rang, H. P. (2003). Pharmacology. Edinburgh: Churchill Livingstone. ISBN 0-443-07145-4.  Page 187
  3. ^ Saxena PR, Lawang A (October 1985). "A comparison of cardiovascular and smooth muscle effects of 5-hydroxytryptamine and 5-carboxamidotryptamine, a selective agonist of 5-HT1 receptors". Arch Int Pharmacodyn Ther 277 (2): 235–52. PMID 2933009. 
  4. ^ Colpaert FC, Niemegeers CJ, Janssen PA (October 1979). "In vivo evidence of partial agonist activity exerted by purported 5-hydroxytryptamine antagonists". Eur. J. Pharmacol. 58 (4): 505–9. doi:10.1016/0014-2999(79)90326-1. PMID 510385. 
  5. ^ a b http://www.patient.co.uk/medicine/Methysergide.htm
  6. ^ a b Joseph T, Tam SK, Kamat BR, Mangion JR (2003). "Successful repair of aortic and mitral incompetence induced by methylsergide maleate: confirmation by intraoperative transesophageal echocardiography". Echocardiography 20 (3): 283–7. doi:10.1046/j.1540-8175.2003.03027.x. PMID 12848667. 
  7. ^ emedicine.com (2002)
  8. ^ 1997 Mayo Clinic study linking heart disease to Fen Phen Valvular heart disease associated with fenfluramine-phentermine
  9. ^ a b Abramson HA, Rolo A (September 1965). "Lysergic acid diethylamide (LSD-25). 38. Comparison with action of methysergide and psilocybin on test subjects". J Asthma Res 3 (1): 81–96. doi:10.3109/02770906509106904. PMID 5318626. 

External links


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Look at other dictionaries:

  • methysergide maleate — A serotonin antagonist, weakly adrenolytic, chemically related to methylergonovine; used in the prophylactic treatment of vascular headache (migraine); untoward effects are common. * * * [USP] the maleate salt of methysergide, having the same… …   Medical dictionary

  • methysergide — noun Etymology: methyl + lysergic acid + amide Date: 1962 a serotonin antagonist C21H27N3O2 used in the form of its maleate especially in the treatment and prevention of migraine headaches …   New Collegiate Dictionary

  • Methysergide — МЕТИСЕРГИД ( Меthysergide )*. N [ a (Гидроксиметил)пропил] 1 метил D лизергамид. Синонимы: Дезерил, Deseril, Dimethylergometrine, Меthylmethergin, Меtisergid, Sansert. Является производным лизергиновой кислоты (см. Алкалоиды спорыньи). По… …   Словарь медицинских препаратов

  • methysergide — /meth euh serr juyd/, n. Pharm. an ergot alkaloid derivative, C21H27N3O2, used in the prophylaxis and treatment of migraine and cluster headaches. [1960 65; METH + (l)yserg(ic) (see LYSERGIC ACID) + IDE] * * * …   Universalium

  • methysergide — noun A prescription drug used for prophylaxis of migraine headaches …   Wiktionary

  • methysergide — meth·y·ser·gide .meth ə sər .jīd n a serotonin antagonist used in the form of its maleate C21H27N3O2·C4H4O4 esp. in the treatment and prevention of migraine headaches * * * n. a drug used to prevent severe migraine attacks and to control… …   Medical dictionary

  • methysergide — methy·ser·gide …   English syllables

  • methysergide — n. a drug used to prevent severe migraine attacks and cluster headaches and to control diarrhoea associated with carcinoid syndrome. Taken by mouth, it is administered under supervision in hospital because it carries a risk of dangerous fibrotic… …   The new mediacal dictionary

  • methysergide — ˌmethəˈsərˌjīd noun ( s) Etymology: methyl + lysergic acid + amide : a serotonin antagonist C21H27N3O2 used as its maleate especially in the treatment and prevention of migraine headaches …   Useful english dictionary

  • Метизергид (Methysergide) — лекарственное вещество; применяется для предотвращения сильных приступов мигрени и прекращения поноса, который наблюдается при различных опухолях пищеварительной системы. Назначается внутрь; возможные побочные эффекты: нарушение процесса… …   Медицинские термины

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