DONITRIPTAN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H25N5O2
Molecular Weight	403.4769
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCCC1=CNC2=C1C=C(OCC(=O)N3CCN(CC3)C4=CC=C(C=C4)C#N)C=C2

InChI

InChIKey=SOHCKWZVTCTQBG-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C23H25N5O2
Molecular Weight	403.4769
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10381763
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 1b (5-HT1b) receptor 46 Target ID: CHEMBL1898 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10381763	Agonist 2678		9.44 null [pKi]
Serotonin 1d (5-HT1d) receptor 52 Target ID: CHEMBL1983 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10381763	Agonist 2678		9.32 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Migraine 103 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11575714	Primary		Phase I 428	Unknown Approved Use Unknown

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	10381763
Donitriptan (Pierre Fabre).	2001 Mar	11575714
Effects of donitriptan on carotid haemodynamics and cardiac output distribution in anaesthetized pigs.	2002 Feb	11993612
Donitriptan selectively decreases jugular venous oxygen saturation in the anesthetized pig: further insights into its mechanism of action relevant to headache relief.	2003 May	12606602
Donitriptan, but not sumatriptan, inhibits capsaicin-induced canine external carotid vasodilatation via 5-HT1B rather than 5-HT1D receptors.	2006 Sep	16880765

Patents

Sample Use Guides

In Vivo Use Guide

guinea pigs: Drugs were administered in 1% methyl cellulose in distilled water

Route of Administration: Oral

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:29:23 UTC 2023` Edited by `admin` on `Sat Dec 16 16:29:23 UTC 2023`
Record UNII	70968BVH2J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DONITRIPTAN

Official Name

English

Donitriptan [WHO-DD]

Common Name

English

donitriptan [INN]

Common Name

English

1-(((3-(2-AMINOETHYL)INDOL-5-YL)OXY)ACETYL)-4-(P-CYANOPHENYL)PIPERAZINE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47794