Avitriptan

 ( 5-ht1b Agonists ) 

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

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Pharmacology

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19 (Ki) 646–>10,000 ()

1.6–21 (Ki) 2.1–2.7 ()

0.78–4.4 (Ki) 0.54 ()

3,550 (Ki) 3,020–>10,000 ()

78–182 (Ki) 81–891 ()

2,340 (Ki) 123 ()

1,150 (Ki) 389 ()

(Ki) ()

>1,000 (rat)

759 (Ki) 4,170 ()

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-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.

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

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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 propyl groupamine side chain instead of the ethyl groupamine 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 cyclic compound and extended.

The predicted log P of avitriptan is 1.8.

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See also

• Triptan
• Donitriptan

Categories: 5-ht1b Agonists, 5-ht1d Agonists, 5-ht2a Agonists, Aromatic Ethers, Aryl Hydrocarbon Receptor Agonists, Piperazines, Pyrimidines, Sulfonamides, Triptans

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