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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 C24H30N4O3
Molecular Weight 422.52
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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

Originator

Pharmacia and Upjohn
22
Curator's Comment: Pharmacia was obtained by Pfizer.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Partial Agonist
297
 4.6 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
141 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/11595000
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PNU-142633 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
100 mg single, oral
Highest studied dose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/10543315
healthy
Health Status: healthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/10543315
Other AEs: Dizziness...
Other AEs:
Dizziness
Sources:
https://pubmed.ncbi.nlm.nih.gov/10543315
AEs

AEs

AESignificanceDosePopulation
Dizziness
100 mg single, oral
Highest studied dose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/10543315
healthy
Health Status: healthy
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/10543315
Sourcing

Sourcing

Vendor/AggregatorIDURL
Alfa Chemistry
11168
http://www.alfa-chemistry.com/search.aspx?q=11168
Alfa Chemistry
AFI187665652
http://www.alfa-chemistry.com/search.aspx?q=AFI187665652
ApexBio Technology
B6906
https://www.apexbt.com/catalogsearch/result/?q=B6906
BOC Sciences
187665-65-2
http://www.bocsci.com/description.asp?cas=187665-65-2
Chem Scene
CS-0024590
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0024590
eMolecules
27315404
https://orderbb.emolecules.com/search/#?query=27315404
MedChem Express
HY-103131
https://www.medchemexpress.com/search.html?q=HY-103131&ft=&fa=&fp=
MolPort
MolPort-023-276-296
https://www.molport.com/shop/molecule-link/MolPort-023-276-296
MuseChem
M038152
https://www.musechem.com/product/M038152.html
Tocris
1985
https://www.tocris.com/search.php?Type=QuickSearch&Value=1985
Toronto Research Chemicals
P653455
https://www.trc-canada.com/product-detail/?CatNum=P653455
Wonderchem
WD05HDO
http://www.wonder-chem.com/search.html?text=WD05HDO
PubMed

PubMed

TitleDatePubMed
Safety and efficacy of PNU-142633, a selective 5-HT1D agonist, in patients with acute migraine.
2001-09
Differential pharmacology between the guinea-pig and the gorilla 5-HT1D receptor as probed with isochromans (5-HT1D-selective ligands).
1999-05
Patents

Patents

EP-0836599-A1
2
S-20140221385-A1
2

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 Mon Mar 31 18:08:32 GMT 2025
Edited
by admin
on Mon Mar 31 18:08:32 GMT 2025
Record UNII
VF98F3655P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PNU-142633F
Preferred Name English
PNU-142633 MALEATE
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
FDA UNII
VF98F3655P
Created by admin on Mon Mar 31 18:08:32 GMT 2025 , Edited by admin on Mon Mar 31 18:08:32 GMT 2025
PRIMARY
CAS
249765-69-3
Created by admin on Mon Mar 31 18:08:32 GMT 2025 , Edited by admin on Mon Mar 31 18:08:32 GMT 2025
PRIMARY
PUBCHEM
10052962
Created by admin on Mon Mar 31 18:08:32 GMT 2025 , Edited by admin on Mon Mar 31 18:08:32 GMT 2025
PRIMARY
Related Record Type Details
Structure of PNU-142633
PARENT -> SALT/SOLVATE
Structure of Maleic Acid
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of PNU-142633
ACTIVE MOIETY
NIH
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