Methysergide
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| 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  |
| ATC code | N02CA04 |
| PubChem | CID 9681 |
| IUPHAR ligand | 134 |
| DrugBank | APRD00463 |
| ChemSpider | 9300 |
| UNII | XZA9HY6Z98 |
| KEGG | D02357 |
| ChEMBL | CHEMBL1065 |
| Chemical data | |
| Formula | C21H27N3O2 |
| Mol. mass | 353.458 g/mol |
| SMILES | eMolecules & PubChem |
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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.
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[edit] 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[5] .
[edit] Uses
Methysergide is used to treat headaches such as migraine and other recurrent throbbing headaches.[6] Methysergide is one of the most effective[7] 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.[6]
[edit] Side effects
It has a known side effect, retroperitoneal fibrosis,[8] 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.[7][9]
[edit] 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.
[edit] Related compounds
Its molecular structure is closely related to that of LSD.
Like LSD, methysergide also produces psychedelic and hallucinogenic effects.[10]
About 4 mg is equal to 25mcg of LSD.[10]
Sandoz does not currently list this on their product guide.
[edit] See also
[edit] References
- ^ 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.
- ^ Rang, H. P. (2003). Pharmacology. Edinburgh: Churchill Livingstone. ISBN 0-443-07145-4. Page 187
- ^ 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.
- ^ 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.
- ^ Bredberg, U.; Eyjolfsdottir, G. S., Paalzow, L., Tfelt-Hansen, P., Tfelt-Hansen, V. (1 January 1986). "Pharmacokinetics of methysergide and its metabolite methylergometrine in man". European Journal of Clinical Pharmacology 30 (1): 75–77. doi:10.1007/BF00614199. PMID 3709634.
- ^ a b http://www.patient.co.uk/medicine/Methysergide.htm
- ^ 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.
- ^ emedicine.com (2002)
- ^ 1997 Mayo Clinic study linking heart disease to Fen Phen Valvular heart disease associated with fenfluramine-phentermine
- ^ 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.
[edit] External links
- Novartis Sansert site.
- Novartis Sansert product description.
- Migraines.org More detailed information on methysergide.
- neurologychannel.com, general information on migraines.
- History of methysergide in migraine.
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