Avitriptan
Chemical compound
Avitriptan (INNTooltip International Nonproprietary Name; 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.
01Pharmacology
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 19 (Ki) 646->10,000 (EC50Tooltip half-maximal effective concentration) |
| 5-HT1B | 1.6-21 (Ki) 2.1-2.7 (EC50) |
| 5-HT1D | 0.78-4.4 (Ki) 0.54 (EC50) |
| 5-HT1E | 3,550 (Ki) 3,020->10,000 (EC50) |
| 5-HT1F | 78-182 (Ki) 81-891 (EC50) |
| 5-HT2A | 2,340 (Ki) 123 (EC50) |
| 5-HT2B | 1,150 (Ki) 389 (EC50) |
| 5-HT2C | ND (Ki) ND (EC50) |
| 5-HT3 | >1,000 (rat) |
| 5-HT4 | ND |
| 5-HT5A | ND |
| 5-HT6 | ND |
| 5-HT7 | 759 (Ki) 4,170 (EC50) |
| α1A, α1D | ND |
| α2A, α2C | ND |
| β1, β3 | ND |
| D1, D5 | ND |
| H1, H4 | ND |
| M1, M5 | ND |
| I1, I2 | ND |
| σ1, σ2 | ND |
| TAAR1Tooltip Trace amine-associated receptor 1 | ND |
| SERTTooltip Serotonin transporter | ND |
| NETTooltip Norepinephrine transporter | ND |
| DATTooltip Dopamine transporter | ND |
| 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 (EC50Tooltip half-maximal effective concentration = 123 nM), 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.
02Chemistry
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 propyl amine side chain instead of the ethyl amine 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.
Sources and credits
This article is adapted from the Wikipedia article “Avitriptan”, written by its contributors and licensed under CC BY-SA 4.0. Fathomly has changed the layout, removed citation markers, navigation and maintenance notices, and adjusted punctuation. This adapted version is shared under the same license. For references, see the original article.
Images, from Wikimedia Commons:
- Avitriptan.svg by AlyInWikiWonderland, Public domain
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