Avitriptan (; development code BMS-180048) is an antimigraine drug of the triptan family which was never marketed. It acts as a serotonin 5-HT1B and 5-HT1D receptor agonist. The drug reached phase 3 clinical trials prior to the discontinuation of its development.
Pharmacology + Target Affinity (Ki, nM) 5-HT1A 19 (Ki)646–>10,000 () 5-HT1B 1.6–21 (Ki)2.1–2.7 () 5-HT1D 0.78–4.4 (Ki)0.54 () 5-HT1E 3,550 (Ki)3,020–>10,000 () 5-HT1F 78–182 (Ki)81–891 () 5-HT2A 2,340 (Ki)123 () 5-HT2B 1,150 (Ki)389 () 5-HT2C (Ki) () 5-HT3 >1,000 (rat) 5-HT4 5-HT5A 5-HT6 5-HT7 759 (Ki)4,170 () α1A–α1D α2A–α2C β1–β3 D1–D5 H1–H4 M1–M5 I1, I2 σ1, σ2 Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs:
Avitriptan acts as a selective serotonin 5-HT1B and 5-HT1D receptor agonist. It is also notable in being a weak serotonin 5-HT2A receptor agonist ( = 123nM), albeit with about two orders of magnitude lower activational potency than at the serotonin 5-HT1B and 5-HT1D receptors.
Besides its activities at serotonin receptors, avitriptan has been found to act as a weak aryl hydrocarbon receptor agonist.
Chemistry Avitriptan is a triptan and a modified analogue of tryptamines like the psychedelic drug dimethyltryptamine (DMT). 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
References