Avitriptan
Chemical compound
title: "Avitriptan" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["5-ht1b-agonists", "5-ht1d-agonists", "5-ht2a-agonists", "aromatic-ethers", "aryl-hydrocarbon-receptor-agonists", "piperazines", "pyrimidines", "sulfonamides", "triptans"] description: "Chemical compound" topic_path: "general/5-ht1b-agonists" source: "https://en.wikipedia.org/wiki/Avitriptan" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
::summary Chemical compound ::
| Verifiedfields = verified | Watchedfields = verified | verifiedrevid = 458783204 | image = Avitriptan.png | image_class = skin-invert-image | width = 250px | image2 = Avitriptan 3D BS.png | image_class2 = bg-transparent | width2 = 250px
| tradename = | pregnancy_category = | legal_status = Never marketed | routes_of_administration = | class = Serotonin 5-HT1B and 5-HT1D receptor agonist; Antimigraine agent; Triptan | ATC_prefix = None | ATC_suffix =
| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
| CAS_number_Ref = | CAS_number = 151140-96-4 | ChEMBL_Ref = | ChEMBL = 2105880 | KEGG_Ref = | KEGG = D03014 | PubChem = 133081 | ChemSpiderID_Ref = | ChemSpiderID = 117442 | UNII_Ref = | UNII = 6RS056L04P | synonyms = BMS-180048; BMS-180,048; BMS180048
| IUPAC_name = 1-[3-[3-[4-(5-methoxypyrimidin-4-yl)piperazin-1-yl]propyl]-1H-indol-5-yl]-N-methyl-methanesulfonamide | C=22 | H=30 | N=6 | O=3 | S=1 | SMILES = O=S(=O)(NC)Cc1ccc2c(c1)c(c[nH]2)CCCN4CCN(c3ncncc3OC)CC4 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = WRZVGHXUPBWIOO-UHFFFAOYSA-N
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
::data[format=table title="{{Nowrap|Avitriptan activities}}"]
| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 19 (Ki) |
| 646–10,000 () | |
| 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 |
| ND | |
| ND | |
| ND | |
| 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 ( = 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.
References
References
- (February 1997). "Effects of avitriptan, a new 5-HT 1B/1D receptor agonist, in experimental models predictive of antimigraine activity and coronary side-effect potential". Naunyn-Schmiedeberg's Archives of Pharmacology.
- (19 July 2025). "Delving into the Latest Updates on Avitriptan with Synapse".
- (October 2003). "5-HT1F receptor agonists in acute migraine treatment: a hypothesis". Cephalalgia.
- (December 2019). "Characterization of binding, functional activity, and contractile responses of the selective 5-HT1F receptor agonist lasmiditan". British Journal of Pharmacology.
- (April 2020). "Antimigraine Drug Avitriptan Is a Ligand and Agonist of Human Aryl Hydrocarbon Receptor That Induces CYP1A1 in Hepatic and Intestinal Cells". Int J Mol Sci.
- "Avitriptan".
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