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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 of DONITRIPTAN

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
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
Donitriptan selectively decreases jugular venous oxygen saturation in the anesthetized pig: further insights into its mechanism of action relevant to headache relief.
2003 May
Donitriptan, but not sumatriptan, inhibits capsaicin-induced canine external carotid vasodilatation via 5-HT1B rather than 5-HT1D receptors.
2006 Sep
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 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
  • Download
Name Type Language
DONITRIPTAN
INN   WHO-DD  
INN  
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
Created by admin on Sat Dec 16 16:29:24 UTC 2023 , Edited by admin on Sat Dec 16 16:29:24 UTC 2023
Code System Code Type Description
PUBCHEM
197706
Created by admin on Sat Dec 16 16:29:24 UTC 2023 , Edited by admin on Sat Dec 16 16:29:24 UTC 2023
PRIMARY
NCI_THESAURUS
C65466
Created by admin on Sat Dec 16 16:29:24 UTC 2023 , Edited by admin on Sat Dec 16 16:29:24 UTC 2023
PRIMARY
MESH
C120143
Created by admin on Sat Dec 16 16:29:24 UTC 2023 , Edited by admin on Sat Dec 16 16:29:24 UTC 2023
PRIMARY
EVMPD
SUB01817MIG
Created by admin on Sat Dec 16 16:29:24 UTC 2023 , Edited by admin on Sat Dec 16 16:29:24 UTC 2023
PRIMARY
CAS
170912-52-4
Created by admin on Sat Dec 16 16:29:24 UTC 2023 , Edited by admin on Sat Dec 16 16:29:24 UTC 2023
PRIMARY
ChEMBL
CHEMBL1742428
Created by admin on Sat Dec 16 16:29:24 UTC 2023 , Edited by admin on Sat Dec 16 16:29:24 UTC 2023
PRIMARY
INN
7874
Created by admin on Sat Dec 16 16:29:24 UTC 2023 , Edited by admin on Sat Dec 16 16:29:24 UTC 2023
PRIMARY
WIKIPEDIA
Donitriptan
Created by admin on Sat Dec 16 16:29:24 UTC 2023 , Edited by admin on Sat Dec 16 16:29:24 UTC 2023
PRIMARY
SMS_ID
100000087525
Created by admin on Sat Dec 16 16:29:24 UTC 2023 , Edited by admin on Sat Dec 16 16:29:24 UTC 2023
PRIMARY
FDA UNII
70968BVH2J
Created by admin on Sat Dec 16 16:29:24 UTC 2023 , Edited by admin on Sat Dec 16 16:29:24 UTC 2023
PRIMARY
EPA CompTox
DTXSID20168974
Created by admin on Sat Dec 16 16:29:24 UTC 2023 , Edited by admin on Sat Dec 16 16:29:24 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY