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SML0422

Sigma-Aldrich

Istradefylline

≥98% (HPLC)

Synonym(s):

(E)-8-(3,4-Dimethoxystyryl)-1,3-diethyl-7-methylxanthine, 8-[(1E)-2-(3,4-Dimethoxyphenyl)ethenyl]-1,3-diethyl-3,7-dihydro-7-methyl-1H-purine-2,6-dione, KW-6002

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About This Item

Empirical Formula (Hill Notation):
C20H24N4O4
CAS Number:
155270-99-8
Molecular Weight:
384.43
MDL number:
MFCD00928421
UNSPSC Code:
12352200
PubChem Substance ID:
329825417
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 5 mg/mL (clear solution)

storage temp.

2-8°C

SMILES string

CCN1C(=O)N(CC)c2nc(\C=C\c3ccc(OC)c(OC)c3)n(C)c2C1=O

InChI

1S/C20H24N4O4/c1-6-23-18-17(19(25)24(7-2)20(23)26)22(3)16(21-18)11-9-13-8-10-14(27-4)15(12-13)28-5/h8-12H,6-7H2,1-5H3/b11-9+

InChI key

IQVRBWUUXZMOPW-PKNBQFBNSA-N

Gene Information

human ... ADORA2A(135)

Biochem/physiol Actions

Istradefylline (KW-6002) is a potent and selective adenosine A2A receptor selective antagonist which has been investigated for use in Parkinson′s Disease.

Features and Benefits

This compound is featured on the Adenosine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Geoffrey B Varty et al.
Psychopharmacology, 200(3), 393-401 (2008-07-03)
Adenosine and dopamine interact within the striatum to control striatopallidal output and globus pallidus GABA release. Manipulating striatal adenosine transmission via blockade of the A2A receptor subtype can compensate for the reduced dopamine activity within the striatum that underlies movement
William Knebel et al.
Journal of clinical pharmacology, 51(1), 40-52 (2010-03-05)
This model-based analysis quantifies the population pharmacokinetics (PK) of orally administered istradefylline, a selective adenosine A(2A) receptor antagonist, in healthy subjects and patients with Parkinson's disease, including the estimation of covariate effects on istradefylline PK parameters. Istradefylline plasma concentration data
Giana P Cognato et al.
Journal of neurochemistry, 112(2), 453-462 (2009-11-03)
Seizures early in life cause long-term behavioral modifications, namely long-term memory deficits in experimental animals. Since caffeine and adenosine A(2A) receptor (A(2A)R) antagonists prevent memory deficits in adult animals, we now investigated if they also prevented the long-term memory deficits
Bo Song et al.
Bioorganic & medicinal chemistry letters, 22(4), 1739-1742 (2012-01-20)
Monoamine oxidase-B (MAO-B) inhibitor has been used as neuroprotectants to treat the motor deficits of Parkinson's disease (PD). We designed and synthesized a class of 8-substituted benzamido-phenylxanthine derivatives as MAO-B inhibitors. The compounds have various inhibitory effects, with compound 6a
Peter Jenner
Expert opinion on investigational drugs, 14(6), 729-738 (2005-07-12)
Dopamine replacement therapy effectively treats the early motor symptoms of Parkinson's disease (PD). However, its association with the development of motor complications limits its usefulness in late stages of the disease. Adenosine A(2A) receptors are localised to the indirect striatal
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