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| Data klinis | |
|---|---|
| Nama dagang | Deseril, Sansert |
| Nama lain | UML-491; 1-Metilmetilergonovina; N-[(2S)-1-Hidroksibutan-2-il]-1,6-dimetil-9,10-didehidroergolina-8α-karboksamida; N-(1-(Hidroksimetil)propil)-1-metil-D-lisergamida |
| AHFS/Drugs.com | |
| MedlinePlus | a603022 |
| Kategori kehamilan |
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| Rute pemberian | Oral[1] |
| Kelas obat | Modulator reseptor monoamina; Antimigrain |
| Kode ATC | |
| Status hukum | |
| Status hukum | |
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| Nomor CAS |
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| PubChem CID | |
| IUPHAR/BPS | |
| DrugBank |
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| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.006.041  |
| Data sifat kimia dan fisik | |
| Rumus | C21H27N3O2 |
| Massa molar | 353,47 g·mol−1 |
| Model 3D (JSmol) | |
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Metisergida adalah obat monoaminergik yang digunakan dalam pencegahan dan pengobatan migrain dan sakit kepala gugus.[2] Obat ini telah ditarik dari pasaran di Amerika Serikat dan Kanada karena masalah keamanan.[1] Obat ini juga diketahui menghasilkan efek psikedelik pada dosis tinggi.[3][4] Obat ini diminum secara oral.[1]
Obat ini merupakan bakal obat dari metilergometrin (metilergonovin), yang bersirkulasi pada tingkat sekitar 10 kali lebih tinggi daripada metisergida.[5][6][7] Sedangkan metisergida adalah agonis campuran dari beberapa reseptor serotonin (misalnya, reseptor serotonin 5-HT1) dan antagonis dari reseptor serotonin lainnya (misalnya, reseptor serotonin 5-HT2), metilergonovin adalah agonis non-selektif dari sebagian besar reseptor serotonin, termasuk subkelompok reseptor serotonin 5-HT1 dan 5-HT2.[8] Metisergida dan metilergometrin adalah ergolina dan lisergamida, dan terkait dengan alkaloid ergot.[9]
Metisergida pertama kali dijelaskan dalam literatur pada tahun 1958.[10][11] Obat ini tidak lagi direkomendasikan sebagai terapi lini pertama untuk migrain atau sakit kepala gugus. Hal ini disebabkan oleh toksisitas seperti valvulopati jantung, yang pertama kali dilaporkan dengan penggunaan jangka panjang pada akhir tahun 1960-an.[12] Obat-obatan berbasis ergot seperti metisergida tidak lagi disukai untuk pengobatan migrain dengan diperkenalkannya triptan pada tahun 1980-an.
Referensi
- 1 2 3 Ramírez Rosas MB, Labruijere S, Villalón CM, Maassen Vandenbrink A (Agustus 2013). "Activation of 5-hydroxytryptamine1B/1D/1F receptors as a mechanism of action of antimigraine drugs". Expert Opinion on Pharmacotherapy. 14 (12): 1599–1610. doi:10.1517/14656566.2013.806487. PMID 23815106. S2CID 22721405.
{{cite journal}}: Pemeliharaan CS1: Tanggal diterjemahkan otomatis (link) - ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. hlm. 677–. ISBN 978-3-88763-075-1.
- ↑ Ott J, Neely P (1980). "Entheogenic (hallucinogenic) effects of methylergonovine". Journal of Psychedelic Drugs. 12 (2): 165–166. doi:10.1080/02791072.1980.10471568. PMID 7420432. A related compound, 1-methyl-d-lysergic acid-(+)-2-butanolamide, a serotonin antagonist marketed as a treatment for migraine by Sandoz under the trade name Sansert® (also known as Deseril®, Methysergide® or UML-491®) has also been shown to be entheogenic at doses of 3.5–7.5 mg (Abramson & Rollo 1967). Evidently Sansert® has roughly the same entheogenic potency as ergonovine, which we estimate to be about 1/200th the potency of LSD. From our limited experience, we estimate that methylergonovine is about 1/40th the potency of LSD.
- ↑ Fanchamps, A. (1978). "Some Compounds With Hallucinogenic Activity". Ergot Alkaloids and Related Compounds. Berlin, Heidelberg: Springer Berlin Heidelberg. hlm. 567–614. doi:10.1007/978-3-642-66775-6_8. ISBN 978-3-642-66777-0. Diakses tanggal 30 Juni 2025. [...] methysergide (UML491, No. 34a), which is the 1-methyl analogue of the purely uterotonic methylergometrine (d-lysergic acid L-2-butanolamide, No. 73a), may produce in some migraine patients mental changes reminiscent of a slight LSD reaction, such as unworldly feelings, dreamy state (GRAHAM, 1964), or even hallucinations (HALE and REED, 1962). According to ABRAMSON (1959), this action amounts to 1% of the effect of LSD.
{{cite book}}: Pemeliharaan CS1: Tanggal diterjemahkan otomatis (link) - ↑ Majrashi M, Ramesh S, Deruiter J, Mulabagal V, Pondugula S, Clark R, Dhanasekaran M (2017). "Multipotent and Poly-therapeutic Fungal Alkaloids of Claviceps purpurea". Dalam Agrawal DC, Tsay HS, Shyur LF, Wu YC, Wang SY (ed.). Medicinal Plants and Fungi: Recent Advances in Research and Development. Medicinal and Aromatic Plants of the World. Vol. 4. hlm. 229–252. doi:10.1007/978-981-10-5978-0_8. ISBN 978-981-10-5977-3. ISSN 2352-6831. Metabolites of methysergide also exhibit pharmacological activity. Methylergometrine (one of methysergide's metabolites) is responsible for methysergide's therapeutic effects regarding migraine treatment (Müller-Schweinitzer and Tapparelli 1986). [...] The systemic availability of methysergide after oral administration is only 13%, due to a high degree of first-pass metabolism by N-1 demethylation to methylergometrine. After oral administration, the plasma concentrations of the metabolite are considerably higher than those of the parent drug, and the area under the plasma concentration curve (AUC) for methylergometrine is more than ten times greater than for methysergide.
- ↑ Rothman RB, Baumann MH, Savage JE, Rauser L, McBride A, Hufeisen SJ, Roth BL (Desember 2000). "Evidence for possible involvement of 5-HT(2B) receptors in the cardiac valvulopathy associated with fenfluramine and other serotonergic medications". Circulation. 102 (23): 2836–2841. doi:10.1161/01.cir.102.23.2836. PMID 11104741.
{{cite journal}}: Pemeliharaan CS1: Tanggal diterjemahkan otomatis (link) - ↑ Leff P (10 April 1998). Receptor - Based Drug Design. CRC Press. hlm. 181–182. ISBN 978-1-4200-0113-6.
{{cite book}}: Pemeliharaan CS1: Tanggal diterjemahkan otomatis (link) - ↑ Guzman M, Armer T, Borland S, Fishman R, Leyden M (April 2020). "Novel Receptor Activity Mapping of Methysergide and its Metabolite, Methylergometrine, Provides a Mechanistic Rationale for both the Clinically Observed Efficacy and Risk of Fibrosis in Patients with Migraine (2663)" (PDF). Neurology. 94 (15 Supplement) 2663. doi:10.1212/WNL.94.15_supplement.2663. S2CID 266103427. Diarsipkan dari asli (PDF) tanggal 2023-05-29.
{{cite journal}}: Pemeliharaan CS1: Tanggal diterjemahkan otomatis (link) - ↑ Keller U, Tudzynski P (2002). "Ergot Alkaloids". Industrial Applications. Berlin, Heidelberg: Springer Berlin Heidelberg. hlm. 157–181. doi:10.1007/978-3-662-10378-4_8. ISBN 978-3-642-07481-3.
- ↑ Doepfner W, Cerletti A (1958). "Comparison of lysergic acid derivatives and antihistamines as inhibitors of the edema provoked in the rat's paw by serotonin". Int Arch Allergy Appl Immunol. 12 (1–2): 89–97. doi:10.1159/000228445. PMID 13549054.
- ↑ Sicuteri F (1959). "Prophylactic and therapeutic properties of 1-methyl-lysergic acid butanolamide in migraine". Int Arch Allergy Appl Immunol. 15 (4–5): 300–307. doi:10.1159/000229055. PMID 14446408.
- ↑ Bana DS, MacNeal PS, LeCompte PM, Shah Y, Graham JR (November 1974). "Cardiac murmurs and endocardial fibrosis associated with methysergide therapy". Am Heart J. 88 (5): 640–655. doi:10.1016/0002-8703(74)90251-8. PMID 4420941.
{{cite journal}}: Pemeliharaan CS1: Tanggal diterjemahkan otomatis (link)
Pranala luar
- Methysergide - Isomer Design
- Novartis Sansert site.
- Novartis Sansert product description.
- Migraines.org More detailed information Diarsipkan 2021-05-05 di Wayback Machine on methysergide.
- neurologychannel.com Diarsipkan 2008-08-29 di Wayback Machine, general information on migraines.
- History of methysergide in migraine.