Avitriptan Explained

Avitriptan (; development code BMS-180048) is an antimigraine drug of the triptan family which was never marketed.^[1] It acts as a serotonin 5-HT_1B and 5-HT_1D receptor agonist. The drug reached phase 3 clinical trials prior to the discontinuation of its development.^[2]

Pharmacology

Avitriptan acts as a selective serotonin 5-HT_1B and 5-HT_1D receptor agonist. It is also notable in being a weak serotonin 5-HT_2A receptor agonist (= 123nM), albeit with about two orders of magnitude lower activational potency than at the serotonin 5-HT_1B and 5-HT_1D receptors.^[5]

Besides its activities at serotonin receptors, avitriptan has been found to act as a weak aryl hydrocarbon receptor agonist.^[6]

Chemistry

Avitriptan is a triptan and a modified analogue of tryptamines like the psychedelic drug dimethyltryptamine (DMT).^[7] However, avitriptan itself is not technically a tryptamine as it features a propylamine side chain instead of the ethylamine side chain present in tryptamines. Besides this difference, avitriptan is substituted at the 5 position of the indole ring system and the amine moiety has been cyclized and extended.

The predicted log P of avitriptan is 1.8.

See also

• Triptan
• Donitriptan

Notes and References

1. Saxena PR, De Vries P, Wang W . Effects of avitriptan, a new 5-HT 1B/1D receptor agonist, in experimental models predictive of antimigraine activity and coronary side-effect potential . Naunyn-Schmiedeberg's Archives of Pharmacology . 355 . 2 . 295–302 . February 1997 . 9050026 . 10.1007/pl00004946 . etal . dead . https://web.archive.org/web/19991023052058/http://link.springer.de/link/service/journals/00210/bibs/7355002/73550295.htm . 1999-10-23 . 1765/66501 . 25137165 . free .
2. Web site: Delving into the Latest Updates on Avitriptan with Synapse . Synapse . 19 July 2025 . 29 July 2025.
3. Ramadan NM, Skljarevski V, Phebus LA, Johnson KW . 5-HT1F receptor agonists in acute migraine treatment: a hypothesis . Cephalalgia . 23 . 8 . 776–785 . October 2003 . 14510923 . 10.1046/j.1468-2982.2003.00525.x .
4. Rubio-Beltrán E, Labastida-Ramírez A, Haanes KA, van den Bogaerdt A, Bogers AJ, Zanelli E, Meeus L, Danser AH, Gralinski MR, Senese PB, Johnson KW, Kovalchin J, Villalón CM, MaassenVanDenBrink A . Characterization of binding, functional activity, and contractile responses of the selective 5-HT_1F receptor agonist lasmiditan . British Journal of Pharmacology . 176 . 24 . 4681–4695 . December 2019 . 31418454 . 6965684 . 10.1111/bph.14832 . TABLE 1 Summary of pIC50 (negative logarithm of the molar concentration of these compounds at which 50% of the radioligand is displaced) and pKi (negative logarithm of the molar concentration of the Ki) values of individual antimigraine drugs at 5‐HT receptors [...] TABLE 2 Summary of pEC50 values of cAMP (5‐HT1A/B/E/F and 5‐HT7), GTPγS (5‐HT1A/B/D/E/F), and IP (5‐HT2) assays of individual antimigraine drugs at 5‐HT receptors [...] .
5. Rubio-Beltrán E, Labastida-Ramírez A, Haanes KA, van den Bogaerdt A, Bogers AJ, Zanelli E, Meeus L, Danser AH, Gralinski MR, Senese PB, Johnson KW, Kovalchin J, Villalón CM, MaassenVanDenBrink A . Characterization of binding, functional activity, and contractile responses of the selective 5-HT_1F receptor agonist lasmiditan . British Journal of Pharmacology . 176 . 24 . 4681–4695 . December 2019 . 31418454 . 6965684 . 10.1111/bph.14832 . TABLE 1 Summary of pIC50 (negative logarithm of the molar concentration of these compounds at which 50% of the radioligand is displaced) and pKi (negative logarithm of the molar concentration of the Ki) values of individual antimigraine drugs at 5‐HT receptors [...] TABLE 2 Summary of pEC50 values of cAMP (5‐HT1A/B/E/F and 5‐HT7), GTPγS (5‐HT1A/B/D/E/F), and IP (5‐HT2) assays of individual antimigraine drugs at 5‐HT receptors [...] .
6. Vyhlídalová B, Krasulová K, Pečinková P, Poulíková K, Vrzal R, Andrysík Z, Chandran A, Mani S, Dvorak Z . Antimigraine Drug Avitriptan Is a Ligand and Agonist of Human Aryl Hydrocarbon Receptor That Induces CYP1A1 in Hepatic and Intestinal Cells . Int J Mol Sci . 21 . 8 . April 2020 . 2799 . 32316498 . 7216230 . 10.3390/ijms21082799 . free .
7. Web site: Avitriptan . PubChem . 29 July 2025.