8-CYCLOPENTYL-1,3-DIPROPYLXANTHINE

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H24N4O2
Molecular Weight	304.3874
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 8-CYCLOPENTYL-1,3-DIPROPYLXANTHINE

Structure Search

SMILES

CCCN1C2=C(N=C(N2)C3CCCC3)C(=O)N(CCC)C1=O

InChI

InChIKey=FFBDFADSZUINTG-UHFFFAOYSA-N

InChI=1S/C16H24N4O2/c1-3-9-19-14-12(15(21)20(10-4-2)16(19)22)17-13(18-14)11-7-5-6-8-11/h11H,3-10H2,1-2H3,(H,17,18)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2825043 | https://www.ncbi.nlm.nih.gov/pubmed/7926579

8-Cyclopentyl-1,3-dipropylxanthine (DPCPX) is a selective high-affinity antagonist radioligand for A1 adenosine receptors. DPCPX is a useful tool with which to explore the potential of activation of adenosine A1 receptors as an important mechanism in physiological and pathophysiological processes.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosine A1 receptor 50 Target ID: CHEMBL226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2825043 \| https://www.ncbi.nlm.nih.gov/pubmed/3561384	Antagonist 2778		0.56 nM [Kd]

Conditions

Condition	Modality	Highest Phase	Product
Alcohol abuse 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26033424	Primary	Preclinical	Unknown Approved Use Unknown
Memory disorders 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25939452 https://www.ncbi.nlm.nih.gov/pubmed/25490060	Primary	Preclinical	Unknown Approved Use Unknown
Arrhythmia 38 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20334814 https://www.ncbi.nlm.nih.gov/pubmed/21907719 https://www.ncbi.nlm.nih.gov/pubmed/20962006	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Binding of [3H]MSX-2 (3-(3-hydroxypropyl)-7-methyl-8-(m-methoxystyryl)-1-propargylxanthine) to rat striatal membranes--a new, selective antagonist radioligand for A(2A) adenosine receptors.	2000	10838015
A1 adenosine receptor activation increases adipocyte leptin secretion.	2000 Apr	10746648
Inducible nitric oxide synthase mediates delayed myocardial protection induced by activation of adenosine A(1) receptors: evidence from gene-knockout mice.	2000 Aug 22	10952960
Estradiol inhibits smooth muscle cell growth in part by activating the cAMP-adenosine pathway.	2000 Jan	10642308
Dissociation between synaptic depression and block of long-term depression induced by raising the temperature in rat hippocampal slices.	2001 Apr	11170219
AMP-activated protein kinase is highly expressed in neurons in the developing rat brain and promotes neuronal survival following glucose deprivation.	2001 Aug	11665862
Control of the proinflammatory state in cystic fibrosis lung epithelial cells by genes from the TNF-alphaR/NFkappaB pathway.	2001 Aug	11591888
Isoflurane-induced protection against myocardial stunning is independent of adenosine 1 (A(1)) receptor in isolated rat heart.	2001 Aug	11493499
Adenosine A3 agonist cardioprotection in isolated rat and rabbit hearts is blocked by the A1 antagonist DPCPX.	2001 Aug	11454590
Adenosine inhibits glutamate exocytosis largely without interfering with Ca2+ influx in rat cerebrocortical synaptosomes.	2001 Aug 31	11514071
Depression of excitatory cortico-nucleus accumbens synaptic transmission in rat brain slices by dopamine, but not adenosine, depends upon intracortical mechanisms.	2001 Dec	11810149
Adenosine inhibits excitatory transmission to substantia gelatinosa neurons of the adult rat spinal cord through the activation of presynaptic A(1) adenosine receptor.	2001 Dec	11731068
Adenosine modulates Mg(2+) uptake in distal convoluted tubule cells via A(1) and A(2) purinoceptors.	2001 Dec	11704566
Activation of presynaptic A1-receptors by endogenous adenosine inhibits acetylcholine release in the guinea-pig ileum.	2001 Feb	11422576
A(2b) receptors mediate the antimitogenic effects of adenosine in cardiac fibroblasts.	2001 Feb	11230362
Regulation of G protein-coupled receptor-adenylyl cyclase responsiveness in human airway smooth muscle by exogenous and autocrine adenosine.	2001 Feb	11159049
Adenosine-enhanced ischemic preconditioning: adenosine receptor involvement during ischemia and reperfusion.	2001 Feb	11158956
G protein activation in rat ponto-mesencephalic nuclei is enhanced by combined treatment with a mu opioid and an adenosine A1 receptor agonist.	2001 Feb 1	11204054
Adenosine A1 receptors regulate the response of the hamster circadian clock to light.	2001 Feb 23	11230994
Adenosine A1 receptor activation reduces reactive oxygen species and attenuates stunning in ventricular myocytes.	2001 Jan	11133228
Withdrawal and bidirectional cross-withdrawal responses in rats treated with adenosine agonists and morphine.	2001 Jul 6	11487090
Agonist-stimulated [35S]GTPgammaS autoradiography: optimization for high sensitivity.	2001 Jun 22	11430907
Relaxation of mouse isolated aorta to adenosine and its analogues does not involve adenosine A(1), A(2) or A(3) receptors.	2001 Mar	11275007
Adenosine receptor-adenylate cyclase system in the trout testis: involvement in the regulation of germ cell proliferation.	2001 Mar	11170272
Electrically evoked release of glutamate in rat hippocampal slices: effects of various drugs and fimbria-fornix lesions.	2001 May	11383708
Neuroprotection by caffeine and A(2A) adenosine receptor inactivation in a model of Parkinson's disease.	2001 May 15	11319241
Effect of adenosine receptor blockade on pial arteriolar dilation during sciatic nerve stimulation.	2001 Nov	11668063
Acute and chronic caffeine administration differentially alters striatal gene expression in wild-type and adenosine A(2A) receptor-deficient mice.	2001 Nov	11574941
Solubilisation and immunoprecipitation of rat striatal adenosine A(2A) receptors.	2001 Nov 16	11728423
Role of adenosine in renal protection induced by a brief episode of ischemic preconditioning in rats.	2001 Oct	11700012
Neuronal mechanisms of the anoxia-induced network oscillations in the rat hippocampus in vitro.	2001 Oct 15	11600686
Inhibitory effect of ischemic preconditioning on leukocyte participation in retinal ischemia-reperfusion injury.	2001 Sep	11527953
Adenosine linking reduced O2 to arteriolar NO release in intestine is not formed from extracellular ATP.	2001 Sep	11514287
[Comparative characteristics of A1-receptor agonists as neuroprotective agents].	2001 Sep-Oct	11764492
Rapid tolerance to focal cerebral ischemia in rats is attenuated by adenosine A1 receptor antagonist.	2002 Feb	11823714
Apparent activation of cardiovascular A1 adenosine receptors by A3 agonists.	2002 Feb	11820196
Pharmacological protection of synaptic function, spatial learning, and memory from transient hypoxia in rats.	2002 Feb	11805198
Use of nasal potential difference and sweat chloride as outcome measures in multicenter clinical trials in subjects with cystic fibrosis.	2002 Feb	11802252
A phase I randomized, multicenter trial of CPX in adult subjects with mild cystic fibrosis.	2002 Feb	11802244
Diverse inhibitors of intracellular signalling act as adenosine receptor antagonists.	2002 Feb	11781134
Intrathecal adenosine following spinal nerve ligation in rat: short residence time in cerebrospinal fluid and no change in A(1) receptor binding.	2002 Jan	11753009
Effects of A(3) adenosine receptor activation and gene knock-out in ischemic-reperfused mouse heart.	2002 Jan	11744023
PDE7A is expressed in human B-lymphocytes and is up-regulated by elevation of intracellular cAMP.	2002 Mar	11812656

Patents

Sample Use Guides

In Vivo Use Guide

Mice: * 3 µg intrathecally * 1, 3, 6 mg/kg systemic administration (i.p.) Rats: 100 ug/kg intravenous

Route of Administration: Other

In Vitro Use Guide

The effects of the A1 adenosine receptor antagonist 1,3-dipropyl-8-cyclopentylxanthine (DPCPX) on force of contraction were examined in isolated electrically driven auricles and papillary muscles from guinea-pigs in the absence and presence of (-)-N6-phenylisopropyladenosine (PIA) and 5'-N-ethylcarboxamidadenosine (NECA). In auricles DPCPX (30-1000 mmol/l) alone increased force of contraction.

Name

Type

Language

8-CYCLOPENTYL-1,3-DIPROPYLXANTHINE

Systematic Name

English

PD-116948

Code

English

1,3-DIPROPYL-8-CYCLOPENTYLXANTHINE

Systematic Name

English

1H-PURINE-2,6-DIONE, 8-CYCLOPENTYL-3,9-DIHYDRO-1,3-DIPROPYL-

Systematic Name

English

CPX

Common Name

English

DPCPX

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

103997