Donitriptan

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	170912-52-4
PubChem (CID)	197706
ChemSpider	171128
UNII	70968BVH2J
ChEMBL	CHEMBL1742428
Chemical and physical data
Formula	C23H25N5O2
Molar mass	403.477 g/mol
3D model (Jmol)	Interactive image
	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 ;

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-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.^[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]

References[edit]

^ Dukat M (March 2001). "Donitriptan (Pierre Fabre)". Curr Opin Investig Drugs. 2 (3): 415–8. PMID 11575714.
^ 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.
^ Jes Olesen (2006). The Headaches. Lippincott Williams & Wilkins. pp. 470–. ISBN 978-0-7817-5400-2.
^ 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.
^ 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.
^ W.W. Fleischhacker; D.J. Brooks (21 May 2003). Neuropsychopharmacology. Springer Vienna. pp. 38–. ISBN 978-3-211-83903-4.
^ 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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[pmid11575714-1] 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.

[Olesen2006-3] Jes Olesen (2006). The Headaches. Lippincott Williams & Wilkins. pp. 470–. ISBN 978-0-7817-5400-2.

[pmid10381763-4] 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.

[BountraMunglani2013-5] 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.

[FleischhackerBrooks2003-6] W.W. Fleischhacker; D.J. Brooks (21 May 2003). Neuropsychopharmacology. Springer Vienna. pp. 38–. ISBN 978-3-211-83903-4.

[Tepper2004-7] 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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v t e Piperazines

Simple piperazines (no additional rings)	1-Cyclohexylpiperazine Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES

Phenylpiperazines	Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin CSP-2503 Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Naphthylpiperazine Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635

Benzylpiperazines	2C-B-BZP Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide Piberaline Piribedil Sunifiram Trimetazidine Vesnarinone

Diphenylalkylpiperazines (benzhydrylalkylpiperazines)	Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,783 GBR-12,935 GBR-13,069 GBR-13,098 GBR-13,119 Hydroxyzine Lidoflazine Manidipine Meclozine Oxatomide SNC-80 Vanoxerine

Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Prazitone Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone

Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine Pyridinylpiperazine

Benzo(iso)thiazolyl piperazines	Lurasidone Perospirone Revospirone Tiospirone Ziprasidone

Tricyclics (piperazine attached via side chain)	Amoxapine Clopenthixol Clorotepine Clozapine Cyanothepin Doclothepin Docloxythepin Flupentixol Fluphenazine Isofloxythepin Loxapine Meperathiepin Metitepine Octomethothepin Olanzapine Opipramol Oxyclothepin Oxyprothepin Peradithiepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Trifluthepin Zuclopenthixol

Others/Uncategorized	6-Nitroquipazine Azimilide Cinepazet Cinepazic acid Cinepazide Cyclohexylpiperazine Hexocyclium Indinavir JNJ-7777120 Lodenafil Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 Zipeprol

Donitriptan

References[edit]

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