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91374-21-9 molecular structure
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4-[2-(dipropylamino)ethyl]-2,3-dihydro-1H-indol-2-one

ChemBase ID: 153
Molecular Formular: C16H24N2O
Molecular Mass: 260.37456
Monoisotopic Mass: 260.1888634
SMILES and InChIs

SMILES:
O=C1Nc2c(c(CCN(CCC)CCC)ccc2)C1
Canonical SMILES:
CCCN(CCC)CCc1cccc2c1CC(=O)N2
InChI:
InChI=1S/C16H24N2O/c1-3-9-18(10-4-2)11-8-13-6-5-7-15-14(13)12-16(19)17-15/h5-7H,3-4,8-12H2,1-2H3,(H,17,19)
InChIKey:
UHSKFQJFRQCDBE-UHFFFAOYSA-N

Cite this record

CBID:153 http://www.chembase.cn/molecule-153.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-[2-(dipropylamino)ethyl]-2,3-dihydro-1H-indol-2-one
IUPAC Traditional name
ropinirole
Brand Name
Requip
ReQuip CR
ReQuip XL
Synonyms
Ropinirol [INN-Spanish]
Ropinirole HCl
Ropinirole hydrochloride
Ropinirolum [INN-Latin]
ropinirole
Ropinirole
CAS Number
91374-21-9
PubChem SID
160963616
46507918
PubChem CID
5095

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 5095 external link
DrugBank DB00268 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.235698  H Acceptors
H Donor LogD (pH = 5.5) -0.4123002 
LogD (pH = 7.4) 0.361759  Log P 3.0607688 
Molar Refractivity 81.4278 cm3 Polarizability 30.66853 Å3
Polar Surface Area 32.34 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.16  LOG S -2.87 
Solubility (Water) 3.53e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
133 mg/mL expand Show data source
Hydrophobicity(logP)
2.3 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00268 external link
Item Information
Drug Groups approved; investigational
Description Ropinirole is a non-ergoline dopamine agonist, manufactured by GlaxoSmithKline. It is used in the treatment of Parkinson's disease, and is also one of two medications in the United States with an FDA-approved indication for the treatment of restless legs syndrome (the other being Pramipexole). [Wikipedia]
Indication For the treatment of the signs and symptoms of idiopathic Parkinson's disease. Also used for the treatment of restless legs syndrome.
Pharmacology Ropinirole is a nonergot dopamine agonist with high relative in vitro specificity and full intrinsic activity at the D2 subfamily of dopamine receptors, binding with higher affinity to D3 than to D2 or D4 receptor subtypes. The relevance of D3 receptor binding in Parkinson's disease is unknown. The mechanism of ropinirole-induced postural hypotension is presumed to be due to a D2 -mediated blunting of the noradrenergic response to standing and subsequent decrease in peripheral vascular resistance.
Toxicity Symptoms of overdose include agitation, chest pain, confusion, drowsiness, facial muscle movements, grogginess, increased jerkiness of movement, symptoms of low blood pressure (dizziness, light-headedness)upon standing, nausea, and vomiting.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. Ropinirole is extensively metabolized to inactive metabolites via N -despropylation and hydroxylation pathways, largely by the P450 isoenzyme CYP1A2. N-despropyl ropinirole is the predominant metabolite found in urine (40%), followed by the carboxylic acid metabolite (10%), and the glucuronide of the hydroxy metabolite (10%).
Absorption Absolute bioavailability is 55%, indicating a first pass effect. Food does not affect the extent of absorption.
Half Life 6 hours
Protein Binding 40% bound to plasma proteins with a blood-to-plasma ratio of 1:1.
Elimination Ropinirole is extensively metabolized by the liver to inactive metabolites, and less than 10% of the administered dose is excreted as unchanged drug in urine.
Distribution * 7.5 L/kg
* 525 L
Clearance * 47 L/hr [after oral administration to Parkinson's disease patients and patients with Restless Legs Syndrome]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

REFERENCES

REFERENCES

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PATENTS

PATENTS

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