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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
Structure of DONITRIPTAN HYDROCHLORIDE

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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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

Curator's Comment: Known to be CNS penetrant in guinea pigs. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
9.44 null [pKi]
9.32 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effects of donitriptan on carotid haemodynamics and cardiac output distribution in anaesthetized pigs.
2002 Feb
Donitriptan selectively decreases jugular venous oxygen saturation in the anesthetized pig: further insights into its mechanism of action relevant to headache relief.
2003 May
Patents

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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:45:44 GMT 2023
Edited
by admin
on Sat Dec 16 10:45:44 GMT 2023
Record UNII
XTD13T14MR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DONITRIPTAN HYDROCHLORIDE
Common Name English
PIPERAZINE, 1-(((3-(2-AMINOETHYL)-1H-INDOL-5-YL)OXY)ACETYL)-4-(4-CYANOPHENYL)-, MONOHYDROCHLORIDE
Systematic Name English
F-11356
Code English
BENZONITRILE, 4-(4-(2-((3-(2-AMINOETHYL)-1H-INDOL-5-YL)OXY)ACETYL)-1-PIPERAZINYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
Code System Code Type Description
PUBCHEM
197705
Created by admin on Sat Dec 16 10:45:44 GMT 2023 , Edited by admin on Sat Dec 16 10:45:44 GMT 2023
PRIMARY
CAS
170911-68-9
Created by admin on Sat Dec 16 10:45:44 GMT 2023 , Edited by admin on Sat Dec 16 10:45:44 GMT 2023
PRIMARY
FDA UNII
XTD13T14MR
Created by admin on Sat Dec 16 10:45:44 GMT 2023 , Edited by admin on Sat Dec 16 10:45:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID60168973
Created by admin on Sat Dec 16 10:45:44 GMT 2023 , Edited by admin on Sat Dec 16 10:45:44 GMT 2023
PRIMARY
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