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;
CompTox Dashboard (EPA)	DTXSID20168974 ;
Chemical and physical data
Formula	C23H25N5O2
Molar mass	403.486 g·mol−1
3D model (JSmol)	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[]

^ 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 Piperazines
Simple piperazines (no additional rings)	Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES
Phenylpiperazines	2C-B-PP 3,4-CFP 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 Fluanisone 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 3-Methylbenzylpiperazine Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide NSI-189 Piberaline Piribedil Sunifiram Trimetazidine Vesnarinone
Diphenylalkylpiperazines (benzhydrylalkylpiperazines)	AD-1211 Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenpipenol Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,935 Hydroxyzine Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine
Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Prazitone Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone
Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine ORG-12962 Pyridinylpiperazine
Benzo(iso)thiazolylpiperazines	Lurasidone Perospirone Revospirone Tiospirone Ziprasidone
Tricyclics (piperazine attached via side chain)	Amoxapine Clopenthixol Clorotepine Clozapine Flupentixol Fluphenazine Loxapine Metitepine Olanzapine Opipramol Oxyprothepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Zuclopenthixol
Others/Uncategorized	6-Nitroquipazine AP-238 Azimilide Bucinnazine Cinepazet Cinepazic acid Cinepazide CPD-1 Cyclohexylpiperazine EGIS-7625 Hexocyclium Indinavir JNJ-7777120 Lodenafil MK-212 Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol

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
CompTox Dashboard (EPA)	DTXSID20168974
Chemical and physical data
Formula	C₂₃H₂₅N₅O₂
Molar mass	403.486 g·mol⁻¹
3D model (JSmol)	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