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

Molecular Formula	C16H24N4O2
Molecular Weight	304.3874
Charge	0
Count

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

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
Pharmacology of airway afferent nerve activity.	2001	11686889
Subchronic treatment with methamphetamine and phencyclidine differentially alters the adenosine A1 and A2A receptors in the prefrontal cortex, hippocampus, and striatum of the rat.	2001 Apr	11495346
2-chloro-N(6)-cyclopentyladenosine-elicited attenuation of evoked glutamate release is not sufficient to give complete protection against pilocarpine-induced seizures in rats.	2001 Apr	11311893
[(35)S]GTPgammaS autoradiography reveals a wide distribution of G(i/o)-linked ADP receptors in the nervous system: close similarities with the platelet P2Y(ADP) receptor.	2001 Apr	11299313
Effect of an adenosine A(1) receptor agonist and a novel pyrimidoindole on membrane properties and neurotransmitter release in rat cortical and hippocampal neurons.	2001 Apr	11222919
A depletable pool of adenosine in area CA1 of the rat hippocampus.	2001 Apr 1	11264305
A functional role for adenosine A3 receptors: modulation of synaptic plasticity in the rat hippocampus.	2001 Apr 13	11278110
AMP-activated protein kinase is highly expressed in neurons in the developing rat brain and promotes neuronal survival following glucose deprivation.	2001 Aug	11665862
Allosteric adenosine modulation to reduce allodynia.	2001 Aug	11506115
Adenosine A3 agonist cardioprotection in isolated rat and rabbit hearts is blocked by the A1 antagonist DPCPX.	2001 Aug	11454590
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
A(2b) receptors mediate the antimitogenic effects of adenosine in cardiac fibroblasts.	2001 Feb	11230362
A1 adenosine receptors inhibit multiple voltage-gated Ca2+ channel subtypes in acutely isolated rat basolateral amygdala neurons.	2001 Feb	11181429
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
Regulation of p42/p44 MAPK and p38 MAPK by the adenosine A(1) receptor in DDT(1)MF-2 cells.	2001 Feb 16	11226388
Adenosine A1 receptors regulate the response of the hamster circadian clock to light.	2001 Feb 23	11230994
Cardioprotective effects of adenosine A1 and A3 receptor activation during hypoxia in isolated rat cardiac myocytes.	2001 Jan	11269659
Characterization of prejunctional purinoceptors inhibiting noradrenaline release in rat mesenteric arteries.	2001 Jan	11243573
Withdrawal and bidirectional cross-withdrawal responses in rats treated with adenosine agonists and morphine.	2001 Jul 6	11487090
Inhibition of calcium channels by opioid- and adenosine-receptor agonists in neurons of the nucleus accumbens.	2001 Jun	11375249
Adenosine A(1) receptor-mediated inhibition of protein kinase A-induced calcitonin gene-related peptide release from rat trigeminal neurons.	2001 Jun	11353815
Poly(lactic acid) microspheres for the sustained release of a selective A1 receptor agonist.	2001 Jun 15	11516507
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 inhibits norepinephrine release in the postischemic rat heart: the mechanism of neuronal stunning.	2001 Mar	11230970
Adenosine receptor-adenylate cyclase system in the trout testis: involvement in the regulation of germ cell proliferation.	2001 Mar	11170272
Adenosine enhances neuroexcitability by inhibiting a slow postspike afterhyperpolarization in rabbit vagal afferent neurons.	2001 Mar 6	11238280
Reduced PO(2) and adenosine formation preserve arteriolar nitric oxide synthesis during sympathetic constriction in the rat intestine.	2001 Mar-Apr	11316946
Electrically evoked release of glutamate in rat hippocampal slices: effects of various drugs and fimbria-fornix lesions.	2001 May	11383708
Ameliorative effects of paeoniflorin, a major constituent of peony root, on adenosine A1 receptor-mediated impairment of passive avoidance performance and long-term potentiation in the hippocampus.	2001 May	11379768
Age-dependent decrease in adenosine A1 receptor binding sites in the rat brain. Effect of cis unsaturated free fatty acids.	2001 May	11358511
Determination of amino acid residues that are accessible from the ligand binding crevice in the seventh transmembrane-spanning region of the human A(1) adenosine receptor.	2001 May	11306703
Receptor subtypes mediating adenosine-induced dilation of cerebral arterioles.	2001 May	11299238
Anti-adrenergic effect of adenosine on Na(+)-Ca(2+) exchange current recorded from guinea-pig ventricular myocytes.	2001 May	11292391
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
Mechanism of intracellular calcium ([Ca2+]i) inhibition of lipolysis in human adipocytes.	2001 Nov	11641262
Acute and chronic caffeine administration differentially alters striatal gene expression in wild-type and adenosine A(2A) receptor-deficient mice.	2001 Nov	11574941
Oxygen delivery and oxygen consumption in rat hindlimb during systemic hypoxia: role of adenosine.	2001 Nov 1	11691884
Activation of synaptic NMDA receptors by action potential-dependent release of transmitter during hypoxia impairs recovery of synaptic transmission on reoxygenation.	2001 Nov 1	11606644
Solubilisation and immunoprecipitation of rat striatal adenosine A(2A) receptors.	2001 Nov 16	11728423
Effects of adenosine receptor agonists and antagonists in a genetic animal model of primary paroxysmal dystonia.	2001 Sep	11564652
Systemic adenosine given after ischemia protects renal function via A(2a) adenosine receptor activation.	2001 Sep	11532695
Adenosine-mediated inhibition of striatal GABAergic synaptic transmission during in vitro ischaemia.	2001 Sep	11522587
Smooth muscle does not have a common P2x receptor phenotype: expression, ontogeny and function of P2x1 receptors in mouse ileum, bladder and reproductive systems.	2001 Sep 17	11570704
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
Diverse inhibitors of intracellular signalling act as adenosine receptor antagonists.	2002 Feb	11781134

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:54:42 GMT 2023` Edited by `admin` on `Fri Dec 15 15:54:42 GMT 2023`
Record UNII	9PTP4FOI9E
Record Status	`Validated (UNII)`
Record Version

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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