Donitriptan

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 4-[4-({[3-(2-Aminoethyl)-1H-indol-5-yl]oxy}acetyl)-1-piperazinyl]benzonitrile

| image = Donitriptan.svg

| CAS_number = 170912-52-4

| ATC_prefix = None

| ATC_suffix =

| PubChem = 197706

| DrugBank =

| ChEMBL = 1742428

| ChemSpiderID = 171128

| UNII = 70968BVH2J

| chemical_formula =

| C=23 | H=25 | N=5 | O=2

| smiles = c1cc(ccc1C#N)N2CCN(CC2)C(=O)COc3ccc4c(c3)c(c[nH]4)CCN

| StdInChI = 1S/C23H25N5O2/c24-8-7-18-15-26-22-6-5-20(13-21(18)22)30-16-23(29)28-11-9-27(10-12-28)19-3-1-17(14-25)2-4-19/h1-6,13,15,26H,7-12,16,24H2

| StdInChIKey = SOHCKWZVTCTQBG-UHFFFAOYSA-N

| bioavailability =

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| metabolism =

| elimination_half-life =

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| pregnancy_AU =

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| legal_US =

| legal_status = Never marketed

| routes_of_administration =

}}

Donitriptan (INN; code name F-11356) is a triptan drug which was investigated as an antimigraine agent but ultimately was never marketed.{{cite journal | vauthors = Dukat M | title = Donitriptan (Pierre Fabre) | journal = Current Opinion in Investigational Drugs | volume = 2 | issue = 3 | pages = 415–418 | date = March 2001 | pmid = 11575714 }} It acts as a high-affinity, high-efficacy/near-full agonist of the 5-HT_1B (pK_i = 9.4–10.1; IA = 94%) and 5-HT_1D receptors (pK_i = 9.3–10.2; IA = 97%), and is among the most potent of the triptan series of drugs.{{cite journal | vauthors = Perez M, Fourrier C, Sigogneau I, Pauwels PJ, Palmier C, John GW, Valentin JP, Halazy S | display-authors = 6 | title = Synthesis and serotonergic activity of arylpiperazide derivatives of serotonin: potent agonists for 5-HT1D receptors | journal = Journal of Medicinal Chemistry | volume = 38 | issue = 18 | pages = 3602–3607 | date = September 1995 | pmid = 7658447 | doi = 10.1021/jm00018a020 }}{{cite book | vauthors = Saxena PR, Tfelt-Hansen P | chapter = Triptans, 5-HT1B/1D Receptor Agonists in the Acute Treatment of Migraine| veditors = Olesen J |title=The Headaches| chapter-url=https://books.google.com/books?id=VXMI1ry9FgQC&pg=PA470|year=2006|publisher=Lippincott Williams & Wilkins|isbn=978-0-7817-5400-2|pages=470–}}{{cite journal | vauthors = John GW, Pauwels PJ, Perez M, Halazy S, Le Grand B, Verscheure Y, Valentin JP, Palmier C, Wurch T, Chopin P, Marien M, Kleven MS, Koek W, Assie MB, Carilla-Durand E, Tarayre JP, Colpaert FC | display-authors = 6 | title = F 11356, a novel 5-hydroxytryptamine (5-HT) derivative with potent, selective, and unique high intrinsic activity at 5-HT1B/1D receptors in models relevant to migraine | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 290 | issue = 1 | pages = 83–95 | date = July 1999 | doi = 10.1016/S0022-3565(24)34871-2 | pmid = 10381763 | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=10381763 }} Donitriptan was being developed in France by bioMérieux-Pierre Fabre and made it to phase II clinical trials in Europe before development was discontinued.{{cite book | vauthors = Schmidt WK | chapter = An Overview of Current and Investigational Drugs for the Treatment of Acute and Chronic Pain | veditors = Bountra C, Munglani R, Schmidt WK |title=Pain: Current Understanding, Emerging Therapies, and Novel Approaches to Drug Discovery| chapter-url = https://books.google.com/books?id=anRzslvfcUwC&pg=PA402|date=28 May 2013|publisher=CRC Press|isbn=978-0-203-91125-9|pages=402–}}{{cite book| vauthors = Fleischhacker WW, Brooks DJ |title=Neuropsychopharmacology|url=https://books.google.com/books?id=1ySUGaXI_wEC&pg=PA38|date=21 May 2003|publisher=Springer Vienna|isbn=978-3-211-83903-4|pages=38–}}{{cite book| vauthors = Tepper SJ | chapter = New Areas of Research |title=Understanding Migraine and Other Headaches| chapter-url=https://archive.org/details/understandingmig00stew |year=2004|publisher=Univ. Press of Mississippi|pages=[https://archive.org/details/understandingmig00stew/page/118 118] | isbn = 978-1-60473-048-7 }}