Avitriptan
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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.
Pharmacology
| 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 = 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.