U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H31N3O3
Molecular Weight 409.5212
Optical Activity ( - )
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PNU-109291

SMILES

CNC(=O)C1=CC=C2[C@H](CCN3CCN(CC3)C4=CC=C(OC)C=C4)OCCC2=C1

InChI

InChIKey=UDLSEQDYARNKTL-QHCPKHFHSA-N
InChI=1S/C24H31N3O3/c1-25-24(28)19-3-8-22-18(17-19)10-16-30-23(22)9-11-26-12-14-27(15-13-26)20-4-6-21(29-2)7-5-20/h3-8,17,23H,9-16H2,1-2H3,(H,25,28)/t23-/m0/s1

HIDE SMILES / InChI
PNU-109291 is a potent and selective 5HT1D receptor agonist. PNU-109291 was able to block neurogenic inflammation in the guinea pig model of migraine.

CNS Activity

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.9 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

In guinea pig model of migraine PNU-109291 was administered intravenously at 1.0 ug/kg. In another study, subcutaneous injection of PNU-109291 in male guinea pigs dose-dependently reduced dural extravasation of [125I]-labeled bovine serum albumin evoked by trigeminal ganglion stimulation with an IC50 of 4.2 nmol kg(-1).
Route of Administration: Other
In Vitro Use Guide
Ki for 5HTD1 was determined using membranes prepared from cloned gorilla receptors expressed in cultured HEK 293 cells. [3H]Serotonin was used as a radioligand. PNU-109291 displaced radioligand with Ki of 0.9 nM. Agonist properties for PNU-109291 were also demonstrated using the GTPgama35S binding assay with cloned gorilla receptors.
Name Type Language
PNU-109291
Code English
PNU109291
Code English
(-)-PNU-109291
Common Name English
(1S)-3,4-DIHYDRO-1-(2-(4-(4-METHOXYPHENYL)-1-PIPERAZINYL)ETHYL)-N-METHYL-1H-2-BENZOPYRAN-6-CARBOXAMIDE
Systematic Name English
S-PNU-109291
Code English
1H-2-BENZOPYRAN-6-CARBOXAMIDE, 3,4-DIHYDRO-1-(2-(4-(4-METHOXYPHENYL)-1-PIPERAZINYL)ETHYL)-N-METHYL-, (1S)-
Systematic Name English
1H-2-BENZOPYRAN-6-CARBOXAMIDE, 3,4-DIHYDRO-1-(2-(4-(4-METHOXYPHENYL)-1-PIPERAZINYL)ETHYL)-N-METHYL-, (S)-
Systematic Name English
Code System Code Type Description
FDA UNII
6E4LJL8K38
Created by admin on Fri Dec 15 16:02:48 GMT 2023 , Edited by admin on Fri Dec 15 16:02:48 GMT 2023
PRIMARY
PUBCHEM
9909448
Created by admin on Fri Dec 15 16:02:48 GMT 2023 , Edited by admin on Fri Dec 15 16:02:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID00442608
Created by admin on Fri Dec 15 16:02:48 GMT 2023 , Edited by admin on Fri Dec 15 16:02:48 GMT 2023
PRIMARY
CAS
187665-60-7
Created by admin on Fri Dec 15 16:02:48 GMT 2023 , Edited by admin on Fri Dec 15 16:02:48 GMT 2023
PRIMARY