Donitriptan

Donitriptan (INN) (code name F-11356) is a triptan drug which was investigated as an antimigraine agent but ultimately was never marketed.[1] It acts as a high-affinity, high-efficacy/near-full agonist of the 5-HT1B (pKi = 9.4–10.1; IA = 94%) and 5-HT1D receptors (pKi = 9.3–10.2; IA = 97%), and is among the most potent of the triptan series of drugs.[2][3][4] Donitriptan was being developed in France by bioMérieux-Pierre Fabre and made it to phase II clinical trials in Europe before development was discontinued.[5][6][7]

Donitriptan
Clinical data
ATC code
  • None
Legal status
Legal status
  • Never marketed
Identifiers
IUPAC name
  • 4-[4-({[3-(2-Aminoethyl)-1H-indol-5-yl]oxy}acetyl)-1-piperazinyl]benzonitrile
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H25N5O2
Molar mass403.486 g·mol−1
3D model (JSmol)
SMILES
  • c1cc(ccc1C#N)N2CCN(CC2)C(=O)COc3ccc4c(c3)c(c[nH]4)CCN
InChI
  • InChI=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
  • Key:SOHCKWZVTCTQBG-UHFFFAOYSA-N

References
  1. Dukat M (March 2001). "Donitriptan (Pierre Fabre)". Curr Opin Investig Drugs. 2 (3): 415–8. PMID 11575714.
  2. Perez M, Fourrier C, Sigogneau I, Pauwels PJ, Palmier C, Valentin JP, John GW, Halazy S (1995) Synthesis and serotonergic activity of arylpiperazide derivatives of serotonin: Potent agonists for 5-HT1D receptors. Journal of Medicinal Chemistry 38:3602–3607.
  3. Jes Olesen (2006). The Headaches. Lippincott Williams & Wilkins. pp. 470–. ISBN 978-0-7817-5400-2.
  4. John GW, Pauwels PJ, Perez M, et al. (July 1999). "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". J. Pharmacol. Exp. Ther. 290 (1): 83–95. PMID 10381763.
  5. Chas Bountra; Rajesh Munglani; William K. Schmidt (28 May 2013). Pain: Current Understanding, Emerging Therapies, and Novel Approaches to Drug Discovery. CRC Press. pp. 402–. ISBN 978-0-203-91125-9.
  6. W.W. Fleischhacker; D.J. Brooks (21 May 2003). Neuropsychopharmacology. Springer Vienna. pp. 38–. ISBN 978-3-211-83903-4.
  7. Stewart J. Tepper (2004). Understanding Migraine and Other Headaches. Univ. Press of Mississippi. pp. 118–. ISBN 978-1-60473-048-7.


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