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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H13N3O.C4H4O4
Molecular Weight 319.3126
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of SUMANIROLE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CN[C@H]1CN2C(=O)NC3=C2C(C1)=CC=C3

InChI

InChIKey=VOJRMYBBPKNLLI-ORHWHDKWSA-N
InChI=1S/C11H13N3O.C4H4O4/c1-12-8-5-7-3-2-4-9-10(7)14(6-8)11(15)13-9;5-3(6)1-2-4(7)8/h2-4,8,12H,5-6H2,1H3,(H,13,15);1-2H,(H,5,6)(H,7,8)/b;2-1-/t8-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C11H13N3O
Molecular Weight 203.2404
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
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
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Sumanirole is a novel dopamine agonist with high affinity and efficacy at D2 dopamine receptors and has a substantial degree of selectivity for the D2 receptor over other dopamine receptor subtypes. It had been in clinical trials for the treatment of Parkinson’s disease and restless leg syndrome but these studies were terminated for the efficacy reason.

CNS Activity

Approval Year

Targets

Targets

Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
U-95666E: a potential anti-parkinsonian drug with anxiolytic activity.
1997 Jul
Effects of selective activation of dopamine D2 and D3 receptors on prolactin secretion and the activity of tuberoinfundibular dopamine neurons.
1997 Sep 17
Dopamine receptor agonists differ in their actions on cardiac ion channels.
2003 Dec 15
Sumanirole Pharmacia.
2003 Jan
Sumanirole, a highly dopamine D2-selective receptor agonist: in vitro and in vivo pharmacological characterization and efficacy in animal models of Parkinson's disease.
2005 Sep
The effects of a selective dopamine D2 receptor agonist on behavioral and pathological outcome in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-treated squirrel monkeys.
2005 Sep
Cardiovascular and electrocardiographic effects of the dopamine receptor agonists ropinirole, apomorphine, and PNU-142774E in conscious beagle dogs.
2006 Mar
Yawning and hypothermia in rats: effects of dopamine D3 and D2 agonists and antagonists.
2007 Aug
Asymmetric synthesis of tetrahydroquinolin-3-ols via CoCl2-catalyzed reductive cyclization of nitro cyclic sulfites with NaBH4.
2009 Feb 19
Patents

Sample Use Guides

In Vivo Use Guide
1 to 16 mg/day
Route of Administration: Oral
In Vitro Use Guide
Sumanirole activated D2 receptor-stimulated mitogenesis with an EC50 of 4.6 nM, but it had no activity at D3 and D4 receptors in measurements of receptor-activated mitogenesis at concentrations up to 1 uM.
Substance Class Chemical
Created
by admin
on Tue Oct 22 19:47:35 UTC 2019
Edited
by admin
on Tue Oct 22 19:47:35 UTC 2019
Record UNII
2OI87T3R1B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SUMANIROLE MALEATE
Common Name English
PNU-95666E
Code English
5,6-DIHYDRO-5-(METHYLAMINO)-4H-IMIDAZO(4,5,1-IJ)QUINOLIN-2(1H)-ONE, R- MALEATE
Common Name English
R)-5,6-DIHYDRO-5-(METHYLAMINO)-4H-IMIDAZO(4,5,1-IJ)QUINOLIN-2(1H)-ONE (2Z)-2-BUTENEDIOATE
Common Name English
U-95666E
Code English
Code System Code Type Description
CAS
179386-44-8
Created by admin on Tue Oct 22 19:47:36 UTC 2019 , Edited by admin on Tue Oct 22 19:47:36 UTC 2019
PRIMARY
MESH
C108539
Created by admin on Tue Oct 22 19:47:36 UTC 2019 , Edited by admin on Tue Oct 22 19:47:36 UTC 2019
PRIMARY
PUBCHEM
9818478
Created by admin on Tue Oct 22 19:47:36 UTC 2019 , Edited by admin on Tue Oct 22 19:47:36 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY