Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C23H25N5O2.ClH |
| Molecular Weight | 439.938 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NCCC1=CNC2=C1C=C(OCC(=O)N3CCN(CC3)C4=CC=C(C=C4)C#N)C=C2
InChI
InChIKey=ZXENQGQAPOYDOJ-UHFFFAOYSA-N
InChI=1S/C23H25N5O2.ClH/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;1H
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11575714
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11575714
Donitriptan hydrochloride (F 11356) was developed by Pierre Fabre as a brain penetrant 5-HT1B/1D agonist. Which inhibits capsaicin-induced external carotid vasodilation and produces selective carotid vasoconstriction in various animal species. In January 2001, donitriptan had completed phase I trials for migraine and was scheduled to enter phase II development, but before development in phase II, this drug was discontinued.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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. | 1999 Jul |
|
| Donitriptan (Pierre Fabre). | 2001 Mar |
|
| Effects of donitriptan on carotid haemodynamics and cardiac output distribution in anaesthetized pigs. | 2002 Feb |
Sample Use Guides
guinea pigs: Drugs were administered in 1% methyl cellulose in distilled water
Route of Administration:
Oral
In C6 rat glioma cells expressing human 5-HT1B or human 5-HT1D receptors, F 11356 (DONITRIPTAN) was the most potent compound in inhibiting forskolin-induced cyclic AMP formation (pD2 = 8.9 and 9.6), and in contrast to tryptamine and derivatives, it produced maximal enhancement of [35S]guanosine-5'-O-(3-thio)triphosphate-specific binding equivalent to 5-HT. F 11356 was equipotent to 5-HT (pD2 = 7.1 versus 7.2) and more potent than tryptamine derivatives in contracting rabbit isolated saphenous vein. In isolated guinea pig trigeminal ganglion neurons, F 11356 was more potent (pD2 = 7.3 versus 6.7) and induced greater increases in outward hyperpolarizing Ca2+-dependent K+ current than sumatriptan.
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197705
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170911-68-9
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XTD13T14MR
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DTXSID60168973
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
