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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

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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Pharmacology of airway afferent nerve activity.
2001
The sulphydryl reagent, N-ethylmaleimide, disrupts sleep and blocks A1 adenosine receptor-mediated inhibition of intracellular calcium signaling in the in vitro ventromedial preoptic nucleus.
2001
Adenosine preferentially suppresses serotonin2A receptor-enhanced excitatory postsynaptic currents in layer V neurons of the rat medial prefrontal cortex.
2001
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
AMP-activated protein kinase is highly expressed in neurons in the developing rat brain and promotes neuronal survival following glucose deprivation.
2001 Aug
Control of the proinflammatory state in cystic fibrosis lung epithelial cells by genes from the TNF-alphaR/NFkappaB pathway.
2001 Aug
Allosteric adenosine modulation to reduce allodynia.
2001 Aug
Isoflurane-induced protection against myocardial stunning is independent of adenosine 1 (A(1)) receptor in isolated rat heart.
2001 Aug
Adenosine receptor antagonists cancelled the ischemic tolerance phenomenon in gerbil.
2001 Aug 10
Adenosine A1 receptors reduce release from excitatory but not inhibitory synaptic inputs onto lateral horn neurons.
2001 Aug 15
Adenosine A(1) receptor agonism in the immature rat brain and heart.
2001 Aug 31
Adenosine inhibits glutamate exocytosis largely without interfering with Ca2+ influx in rat cerebrocortical synaptosomes.
2001 Aug 31
Depression of excitatory cortico-nucleus accumbens synaptic transmission in rat brain slices by dopamine, but not adenosine, depends upon intracortical mechanisms.
2001 Dec
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
Antagonism of adenosine A(1) receptors in the NTS does not affect the chemoreflex in awake rats.
2001 Dec
Adenosine modulates Mg(2+) uptake in distal convoluted tubule cells via A(1) and A(2) purinoceptors.
2001 Dec
Regulation of K(+) current in human airway epithelial cells by exogenous and autocrine adenosine.
2001 Dec
Modulation of ethanol-induced motor incoordination by mouse striatal A(1) adenosinergic receptor.
2001 Jul 1
Withdrawal and bidirectional cross-withdrawal responses in rats treated with adenosine agonists and morphine.
2001 Jul 6
Poly(lactic acid) microspheres for the sustained release of a selective A1 receptor agonist.
2001 Jun 15
Effect of adenosine receptor blockade on pial arteriolar dilation during sciatic nerve stimulation.
2001 Nov
Mechanism of intracellular calcium ([Ca2+]i) inhibition of lipolysis in human adipocytes.
2001 Nov
Modulation of N-type Ca2+ currents by A1-adenosine receptor activation in male rat pelvic ganglion neurons.
2001 Nov
Cell-based assay for high-throughput quantitative screening of CFTR chloride transport agonists.
2001 Nov
Acute and chronic caffeine administration differentially alters striatal gene expression in wild-type and adenosine A(2A) receptor-deficient mice.
2001 Nov
Oxygen delivery and oxygen consumption in rat hindlimb during systemic hypoxia: role of adenosine.
2001 Nov 1
Activation of synaptic NMDA receptors by action potential-dependent release of transmitter during hypoxia impairs recovery of synaptic transmission on reoxygenation.
2001 Nov 1
Solubilisation and immunoprecipitation of rat striatal adenosine A(2A) receptors.
2001 Nov 16
Role of adenosine in renal protection induced by a brief episode of ischemic preconditioning in rats.
2001 Oct
Adenosine-mediated hypotension in in vivo guinea-pig: receptors involved and role of NO.
2001 Oct
Neuronal mechanisms of the anoxia-induced network oscillations in the rat hippocampus in vitro.
2001 Oct 15
Effects of adenosine receptor agonists and antagonists in a genetic animal model of primary paroxysmal dystonia.
2001 Sep
Systemic adenosine given after ischemia protects renal function via A(2a) adenosine receptor activation.
2001 Sep
Inhibitory effect of ischemic preconditioning on leukocyte participation in retinal ischemia-reperfusion injury.
2001 Sep
The plasma protein extravasation induced by adenosine and its analogues in the rat dorsal skin: evidence for the involvement of capsaicin sensitive primary afferent neurones and mast cells.
2001 Sep
Adenosine-mediated inhibition of striatal GABAergic synaptic transmission during in vitro ischaemia.
2001 Sep
Adenosine linking reduced O2 to arteriolar NO release in intestine is not formed from extracellular ATP.
2001 Sep
Amp 579 reduces contracture and limits infarction in rabbit heart by activating adenosine A2 receptors.
2001 Sep
Effects of angiotensin III and angiotensin IV on pentylenetetrazol seizure susceptibility (threshold and kindling): interaction with adenosine A(1) receptors.
2001 Sep 15
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
[Comparative characteristics of A1-receptor agonists as neuroprotective agents].
2001 Sep-Oct
Rapid tolerance to focal cerebral ischemia in rats is attenuated by adenosine A1 receptor antagonist.
2002 Feb
Apparent activation of cardiovascular A1 adenosine receptors by A3 agonists.
2002 Feb
Pharmacological protection of synaptic function, spatial learning, and memory from transient hypoxia in rats.
2002 Feb
Use of nasal potential difference and sweat chloride as outcome measures in multicenter clinical trials in subjects with cystic fibrosis.
2002 Feb
A phase I randomized, multicenter trial of CPX in adult subjects with mild cystic fibrosis.
2002 Feb
Diverse inhibitors of intracellular signalling act as adenosine receptor antagonists.
2002 Feb
Intrathecal adenosine following spinal nerve ligation in rat: short residence time in cerebrospinal fluid and no change in A(1) receptor binding.
2002 Jan
Effects of A(3) adenosine receptor activation and gene knock-out in ischemic-reperfused mouse heart.
2002 Jan
PDE7A is expressed in human B-lymphocytes and is up-regulated by elevation of intracellular cAMP.
2002 Mar
Patents

Patents

Sample Use Guides

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
  • Download
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
Created by admin on Fri Dec 15 15:54:42 GMT 2023 , Edited by admin on Fri Dec 15 15:54:42 GMT 2023
Code System Code Type Description
PUBCHEM
1329
Created by admin on Fri Dec 15 15:54:42 GMT 2023 , Edited by admin on Fri Dec 15 15:54:42 GMT 2023
PRIMARY
CAS
102146-07-6
Created by admin on Fri Dec 15 15:54:42 GMT 2023 , Edited by admin on Fri Dec 15 15:54:42 GMT 2023
PRIMARY
CHEBI
73282
Created by admin on Fri Dec 15 15:54:42 GMT 2023 , Edited by admin on Fri Dec 15 15:54:42 GMT 2023
PRIMARY
DRUG BANK
DB12946
Created by admin on Fri Dec 15 15:54:42 GMT 2023 , Edited by admin on Fri Dec 15 15:54:42 GMT 2023
PRIMARY
WIKIPEDIA
Dipropylcyclopentylxanthine
Created by admin on Fri Dec 15 15:54:42 GMT 2023 , Edited by admin on Fri Dec 15 15:54:42 GMT 2023
PRIMARY
FDA UNII
9PTP4FOI9E
Created by admin on Fri Dec 15 15:54:42 GMT 2023 , Edited by admin on Fri Dec 15 15:54:42 GMT 2023
PRIMARY
SMS_ID
100000178229
Created by admin on Fri Dec 15 15:54:42 GMT 2023 , Edited by admin on Fri Dec 15 15:54:42 GMT 2023
PRIMARY
EPA CompTox
DTXSID50144706
Created by admin on Fri Dec 15 15:54:42 GMT 2023 , Edited by admin on Fri Dec 15 15:54:42 GMT 2023
PRIMARY
EVMPD
SUB193832
Created by admin on Fri Dec 15 15:54:42 GMT 2023 , Edited by admin on Fri Dec 15 15:54:42 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
BINDING
IC50
LABELED -> NON-LABELED
TARGET -> INHIBITOR
IC50
Related Record Type Details
ACTIVE MOIETY