SUMANIROLE MALEATE

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 Search

SMILES

OC(=O)\C=C/C(O)=O.CN[C@H]1CN2C(=O)NC3=CC=CC(C1)=C23

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	C4H4O4
Molecular Weight	116.0722
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Molecular Formula	C11H13N3O
Molecular Weight	203.2404
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15980060 | https://www.ncbi.nlm.nih.gov/pubmed/17318839 | https://www.ncbi.nlm.nih.gov/pubmed/17239657

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Dopamine D2 receptor 297 Target ID: CHEMBL339 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9057850 \| DOI: 10.1021/jo970526a	Agonist 2678	12.0 nM [Ki]
Dopamine D3 receptor 91 Target ID: CHEMBL3138 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9057850	Binding Agent 1064	1.9 µM [Ki]
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL273 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9057850	Binding Agent 1064	92.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17318839	Primary		Phase III 656	Unknown Approved Use Unknown
Restless legs syndrome 16 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17239657	Primary		Phase II 1132	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
1 mg 1 times / day multiple, oral (unknown) Studied dose Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17239657	unhealthy n = 49 Health Status: unhealthy Condition: restless legs syndrome Sex: M+F Food Status: UNKNOWN Population Size: 49 Sources: https://pubmed.ncbi.nlm.nih.gov/17239657	Disc. AE: dizziness, Headaches... AEs leading to discontinuation/dose reduction: dizziness (1 pt) Headaches (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/17239657
2 mg 1 times / day multiple, oral (unknown) Studied dose Dose: 2 mg, 1 times / day Route: oral Route: multiple Dose: 2 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17239657	unhealthy n = 59 Health Status: unhealthy Condition: restless legs syndrome Sex: M+F Food Status: UNKNOWN Population Size: 59 Sources: https://pubmed.ncbi.nlm.nih.gov/17239657	Disc. AE: Nausea and vomiting, Dizziness... AEs leading to discontinuation/dose reduction: Nausea and vomiting (1 pt) Dizziness (1 pt) insomnia (1 pt) dizziness (1 pt) diarrhea (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/17239657

AEs

AE	Significance	Dose	Population
Headaches	1 pt Disc. AE	1 mg 1 times / day multiple, oral (unknown) Studied dose Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17239657	unhealthy n = 49 Health Status: unhealthy Condition: restless legs syndrome Sex: M+F Food Status: UNKNOWN Population Size: 49 Sources: https://pubmed.ncbi.nlm.nih.gov/17239657
dizziness	1 pt Disc. AE	1 mg 1 times / day multiple, oral (unknown) Studied dose Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17239657	unhealthy n = 49 Health Status: unhealthy Condition: restless legs syndrome Sex: M+F Food Status: UNKNOWN Population Size: 49 Sources: https://pubmed.ncbi.nlm.nih.gov/17239657
Dizziness	1 pt Disc. AE	2 mg 1 times / day multiple, oral (unknown) Studied dose Dose: 2 mg, 1 times / day Route: oral Route: multiple Dose: 2 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17239657	unhealthy n = 59 Health Status: unhealthy Condition: restless legs syndrome Sex: M+F Food Status: UNKNOWN Population Size: 59 Sources: https://pubmed.ncbi.nlm.nih.gov/17239657
Nausea and vomiting	1 pt Disc. AE	2 mg 1 times / day multiple, oral (unknown) Studied dose Dose: 2 mg, 1 times / day Route: oral Route: multiple Dose: 2 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17239657	unhealthy n = 59 Health Status: unhealthy Condition: restless legs syndrome Sex: M+F Food Status: UNKNOWN Population Size: 59 Sources: https://pubmed.ncbi.nlm.nih.gov/17239657
diarrhea	1 pt Disc. AE	2 mg 1 times / day multiple, oral (unknown) Studied dose Dose: 2 mg, 1 times / day Route: oral Route: multiple Dose: 2 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17239657	unhealthy n = 59 Health Status: unhealthy Condition: restless legs syndrome Sex: M+F Food Status: UNKNOWN Population Size: 59 Sources: https://pubmed.ncbi.nlm.nih.gov/17239657
dizziness	1 pt Disc. AE	2 mg 1 times / day multiple, oral (unknown) Studied dose Dose: 2 mg, 1 times / day Route: oral Route: multiple Dose: 2 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17239657	unhealthy n = 59 Health Status: unhealthy Condition: restless legs syndrome Sex: M+F Food Status: UNKNOWN Population Size: 59 Sources: https://pubmed.ncbi.nlm.nih.gov/17239657
insomnia	1 pt Disc. AE	2 mg 1 times / day multiple, oral (unknown) Studied dose Dose: 2 mg, 1 times / day Route: oral Route: multiple Dose: 2 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17239657	unhealthy n = 59 Health Status: unhealthy Condition: restless legs syndrome Sex: M+F Food Status: UNKNOWN Population Size: 59 Sources: https://pubmed.ncbi.nlm.nih.gov/17239657

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00ACFM	https://www.1pchem.com/search?query=1P00ACFM
AK Scientific	2736AH	https://aksci.com/item_detail.php?cat=2736AH
AK Scientific	9411AA	https://aksci.com/item_detail.php?cat=9411AA
Alfa Chemistry	10730	http://www.alfa-chemistry.com/search.aspx?q=10730
Alfa Chemistry	AFI179386437	http://www.alfa-chemistry.com/search.aspx?q=AFI179386437
Angene	AGN-PC-0QBJSH	http://www.angenechemical.com/productshow/AGN-PC-0QBJSH.html
AstaTech	C15124	http://astatechinc.com/CPSResult.php?CRNO=C15124
BLD Pharm	BD211759	http://www.bldpharm.com/search/Search.html?keyword=BD211759
BLD Pharm	BD237583	http://www.bldpharm.com/search/Search.html?keyword=BD237583
BOC Sciences	179386-43-7	http://www.bocsci.com/description.asp?cas=179386-43-7
BioSynth	J-502234	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/J-502234
Chem Scene	CS-0353	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0353
Chemspace	CSC010542382	https://chem-space.com/CSC010542382
Chemspace	CSC020617428	https://chem-space.com/CSC020617428
Enamine	BBV-45354007	http://www.enaminestore.com/catalog/BBV-45354007
Enamine	BBV-78367068	http://www.enaminestore.com/catalog/BBV-78367068
Lab Network	LN01308896	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01308896
MedChem Express	HY-70081A	https://www.medchemexpress.com/search.html?q=HY-70081A&ft=&fa=&fp=
MolPort	MolPort-016-633-302	https://www.molport.com/shop/molecule-link/MolPort-016-633-302
MuseChem	I009644	https://www.musechem.com/product/I009644.html
MuseChem	R055708	https://www.musechem.com/product/R055708.html
Tocris	2773	https://www.tocris.com/search.php?Type=QuickSearch&Value=2773
Toronto Research Chemicals	S790700	https://www.trc-canada.com/product-detail/?CatNum=S790700
Wonderchem	WD05FV8	http://www.wonder-chem.com/search.html?text=WD05FV8
eMolecules	295312209	https://orderbb.emolecules.com/search/#?query=295312209
eMolecules	43552341	https://orderbb.emolecules.com/search/#?query=43552341
eMolecules	44469286	https://orderbb.emolecules.com/search/#?query=44469286
eMolecules	44850119	https://orderbb.emolecules.com/search/#?query=44850119
eMolecules	45956641	https://orderbb.emolecules.com/search/#?query=45956641
mcule	MCULE-3614404271	https://mcule.com/MCULE-3614404271/
mcule	MCULE-7038027467	https://mcule.com/MCULE-7038027467/
mcule	MCULE-7344325631	https://mcule.com/MCULE-7344325631/
mcule	MCULE-8361013753	https://mcule.com/MCULE-8361013753/

PubMed

Title	Date	PubMed
Effects of selective activation of dopamine D2 and D3 receptors on prolactin secretion and the activity of tuberoinfundibular dopamine neurons.	1997 Sep 17	9371544
Dopamine receptor agonists differ in their actions on cardiac ion channels.	2003 Dec 15	14660002
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	15980058

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 `Sat Dec 16 05:16:17 GMT 2023` Edited by `admin` on `Sat Dec 16 05:16:17 GMT 2023`
Record UNII	2OI87T3R1B
Record Status	`Validated (UNII)`
Record Version

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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

DRUG BANK

DBSALT002019