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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H30N4O3.C4H4O4
Molecular Weight 538.5922
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PNU-142633 MALEATE

SMILES

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

InChI

InChIKey=GYOIZJALBHBRIJ-PCBAQXHCSA-N
InChI=1S/C24H30N4O3.C4H4O4/c1-26-24(30)19-4-7-21-18(16-19)9-15-31-22(21)8-10-27-11-13-28(14-12-27)20-5-2-17(3-6-20)23(25)29;5-3(6)1-2-4(7)8/h2-7,16,22H,8-15H2,1H3,(H2,25,29)(H,26,30);1-2H,(H,5,6)(H,7,8)/b;2-1-/t22-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C24H30N4O3
Molecular Weight 422.52
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

PNU-142633 is selective 5HT1D partial agonist, developed by Pharmacia & Upjohn, Inc. It failed in phase II clinical trials against acute migraine, and its development was discontinued.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
4.6 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PubMed

PubMed

TitleDatePubMed
Differential pharmacology between the guinea-pig and the gorilla 5-HT1D receptor as probed with isochromans (5-HT1D-selective ligands).
1999 May
Safety and efficacy of PNU-142633, a selective 5-HT1D agonist, in patients with acute migraine.
2001 Sep
Patents

Sample Use Guides

In Vivo Use Guide
In phase II clinical trials patients received a single 50-mg oral dose of a 5-HT(1D) agonist, PNU-142633 during an acute migraine attack.
Route of Administration: Oral
In Vitro Use Guide
Receptor binding studies were performed on 5HT1D receptors, expressed in HEK293 cells. Binding of [3H]-serotonin was measured in membranes, using filtration techniques.
Substance Class Chemical
Created
by admin
on Tue Oct 22 17:48:50 UTC 2019
Edited
by admin
on Tue Oct 22 17:48:50 UTC 2019
Record UNII
VF98F3655P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PNU-142633 MALEATE
Common Name English
PNU-142633F
Common Name English
1H-2-BENZOPYRAN-6-CARBOXAMIDE, 1-(2-(4-(4-(AMINOCARBONYL)PHENYL)-1-PIPERAZINYL)ETHYL)-3,4-DIHYDRO-N-METHYL-, (1S)-, (2Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
Code System Code Type Description
WIKIPEDIA
PNU-142633
Created by admin on Tue Oct 22 17:48:51 UTC 2019 , Edited by admin on Tue Oct 22 17:48:51 UTC 2019
PRIMARY
CAS
249765-69-3
Created by admin on Tue Oct 22 17:48:51 UTC 2019 , Edited by admin on Tue Oct 22 17:48:51 UTC 2019
PRIMARY
PUBCHEM
10052962
Created by admin on Tue Oct 22 17:48:51 UTC 2019 , Edited by admin on Tue Oct 22 17:48:51 UTC 2019
PRIMARY
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