Avitriptan

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Avitriptan
Clinical data
Other namesBMS-180048; BMS-180,048; BMS180048
Drug classSerotonin 5-HT1B and 5-HT1D receptor agonist; Antimigraine agent; Triptan
ATC code
  • None
Legal status
Legal status
  • Never marketed
Identifiers
  • 1-[3-[3-[4-(5-methoxypyrimidin-4-yl)piperazin-1-yl]propyl]-1H-indol-5-yl]-N-methyl-methanesulfonamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC22H30N6O3S
Molar mass458.58 g·mol−1
3D model (JSmol)
  • O=S(=O)(NC)Cc1ccc2c(c1)c(c[nH]2)CCCN4CCN(c3ncncc3OC)CC4
  • InChI=1S/C22H30N6O3S/c1-23-32(29,30)15-17-5-6-20-19(12-17)18(13-25-20)4-3-7-27-8-10-28(11-9-27)22-21(31-2)14-24-16-26-22/h5-6,12-14,16,23,25H,3-4,7-11,15H2,1-2H3 checkY
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  (verify)

Avitriptan (INNTooltip International Nonproprietary Name; development code BMS-180048) is an antimigraine drug of the triptan family which was never marketed.[1] It acts as a serotonin 5-HT1B and 5-HT1D receptor agonist.[1][2] The drug reached phase 3 clinical trials prior to the discontinuation of its development.[3]

Pharmacology

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Avitriptan activities
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: [1][4][2]

Avitriptan acts as a selective serotonin 5-HT1B and 5-HT1D receptor agonist.[1][2] 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.[2]

Besides its activities at serotonin receptors, avitriptan has been found to act as a weak aryl hydrocarbon receptor agonist.[5]

Chemistry

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Avitriptan is a triptan and a modified analogue of tryptamines like the psychedelic drug dimethyltryptamine (DMT).[6] However, avitriptan itself is not technically a tryptamine as it features a propylamine side chain instead of the ethylamine side chain present in tryptamines.[6] Besides this difference, avitriptan is substituted at the 5 position of the indole ring system and the amine moiety has been cyclized and extended.[6]

The predicted log P of avitriptan is 1.8.[6]

See also

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References

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