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
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)
| 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
| Title | Date | PubMed |
|---|---|---|
| PDE7A is expressed in human B-lymphocytes and is up-regulated by elevation of intracellular cAMP. | 2002-03 |
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| Rapid tolerance to focal cerebral ischemia in rats is attenuated by adenosine A1 receptor antagonist. | 2002-02 |
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| Apparent activation of cardiovascular A1 adenosine receptors by A3 agonists. | 2002-02 |
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| Pharmacological protection of synaptic function, spatial learning, and memory from transient hypoxia in rats. | 2002-02 |
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| Use of nasal potential difference and sweat chloride as outcome measures in multicenter clinical trials in subjects with cystic fibrosis. | 2002-02 |
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| A phase I randomized, multicenter trial of CPX in adult subjects with mild cystic fibrosis. | 2002-02 |
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| Diverse inhibitors of intracellular signalling act as adenosine receptor antagonists. | 2002-02 |
|
| [Comparative characteristics of A1-receptor agonists as neuroprotective agents]. | 2002-01-05 |
|
| Intrathecal adenosine following spinal nerve ligation in rat: short residence time in cerebrospinal fluid and no change in A(1) receptor binding. | 2002-01 |
|
| Effects of A(3) adenosine receptor activation and gene knock-out in ischemic-reperfused mouse heart. | 2002-01 |
|
| Depression of excitatory cortico-nucleus accumbens synaptic transmission in rat brain slices by dopamine, but not adenosine, depends upon intracortical mechanisms. | 2001-12 |
|
| Adenosine inhibits excitatory transmission to substantia gelatinosa neurons of the adult rat spinal cord through the activation of presynaptic A(1) adenosine receptor. | 2001-12 |
|
| Antagonism of adenosine A(1) receptors in the NTS does not affect the chemoreflex in awake rats. | 2001-12 |
|
| Adenosine modulates Mg(2+) uptake in distal convoluted tubule cells via A(1) and A(2) purinoceptors. | 2001-12 |
|
| Regulation of K(+) current in human airway epithelial cells by exogenous and autocrine adenosine. | 2001-12 |
|
| Solubilisation and immunoprecipitation of rat striatal adenosine A(2A) receptors. | 2001-11-16 |
|
| Oxygen delivery and oxygen consumption in rat hindlimb during systemic hypoxia: role of adenosine. | 2001-11-01 |
|
| Activation of synaptic NMDA receptors by action potential-dependent release of transmitter during hypoxia impairs recovery of synaptic transmission on reoxygenation. | 2001-11-01 |
|
| Effect of adenosine receptor blockade on pial arteriolar dilation during sciatic nerve stimulation. | 2001-11 |
|
| Mechanism of intracellular calcium ([Ca2+]i) inhibition of lipolysis in human adipocytes. | 2001-11 |
|
| Modulation of N-type Ca2+ currents by A1-adenosine receptor activation in male rat pelvic ganglion neurons. | 2001-11 |
|
| Cell-based assay for high-throughput quantitative screening of CFTR chloride transport agonists. | 2001-11 |
|
| Acute and chronic caffeine administration differentially alters striatal gene expression in wild-type and adenosine A(2A) receptor-deficient mice. | 2001-11 |
|
| Neuronal mechanisms of the anoxia-induced network oscillations in the rat hippocampus in vitro. | 2001-10-15 |
|
| Role of adenosine in renal protection induced by a brief episode of ischemic preconditioning in rats. | 2001-10 |
|
| Adenosine-mediated hypotension in in vivo guinea-pig: receptors involved and role of NO. | 2001-10 |
|
| Smooth muscle does not have a common P2x receptor phenotype: expression, ontogeny and function of P2x1 receptors in mouse ileum, bladder and reproductive systems. | 2001-09-17 |
|
| Effects of angiotensin III and angiotensin IV on pentylenetetrazol seizure susceptibility (threshold and kindling): interaction with adenosine A(1) receptors. | 2001-09-15 |
|
| Effects of adenosine receptor agonists and antagonists in a genetic animal model of primary paroxysmal dystonia. | 2001-09 |
|
| Systemic adenosine given after ischemia protects renal function via A(2a) adenosine receptor activation. | 2001-09 |
|
| Inhibitory effect of ischemic preconditioning on leukocyte participation in retinal ischemia-reperfusion injury. | 2001-09 |
|
| 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. | 2001-09 |
|
| Adenosine-mediated inhibition of striatal GABAergic synaptic transmission during in vitro ischaemia. | 2001-09 |
|
| Adenosine linking reduced O2 to arteriolar NO release in intestine is not formed from extracellular ATP. | 2001-09 |
|
| Amp 579 reduces contracture and limits infarction in rabbit heart by activating adenosine A2 receptors. | 2001-09 |
|
| Adenosine A(1) receptor agonism in the immature rat brain and heart. | 2001-08-31 |
|
| Adenosine inhibits glutamate exocytosis largely without interfering with Ca2+ influx in rat cerebrocortical synaptosomes. | 2001-08-31 |
|
| Adenosine A1 receptors reduce release from excitatory but not inhibitory synaptic inputs onto lateral horn neurons. | 2001-08-15 |
|
| Adenosine receptor antagonists cancelled the ischemic tolerance phenomenon in gerbil. | 2001-08-10 |
|
| AMP-activated protein kinase is highly expressed in neurons in the developing rat brain and promotes neuronal survival following glucose deprivation. | 2001-08 |
|
| Control of the proinflammatory state in cystic fibrosis lung epithelial cells by genes from the TNF-alphaR/NFkappaB pathway. | 2001-08 |
|
| Allosteric adenosine modulation to reduce allodynia. | 2001-08 |
|
| Isoflurane-induced protection against myocardial stunning is independent of adenosine 1 (A(1)) receptor in isolated rat heart. | 2001-08 |
|
| Withdrawal and bidirectional cross-withdrawal responses in rats treated with adenosine agonists and morphine. | 2001-07-06 |
|
| Modulation of ethanol-induced motor incoordination by mouse striatal A(1) adenosinergic receptor. | 2001-07-01 |
|
| Poly(lactic acid) microspheres for the sustained release of a selective A1 receptor agonist. | 2001-06-15 |
|
| Subchronic treatment with methamphetamine and phencyclidine differentially alters the adenosine A1 and A2A receptors in the prefrontal cortex, hippocampus, and striatum of the rat. | 2001-04 |
|
| 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 |
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
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
Edited
Mon Mar 31 18:12:57 GMT 2025
by
admin
on
Mon Mar 31 18:12:57 GMT 2025
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| Record UNII |
9PTP4FOI9E
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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Preferred Name | English | ||
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Systematic Name | English | ||
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
103997
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| Code System | Code | Type | Description | ||
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1329
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102146-07-6
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73282
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DB12946
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Dipropylcyclopentylxanthine
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9PTP4FOI9E
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100000178229
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DTXSID50144706
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SUB193832
Created by
admin on Mon Mar 31 18:12:57 GMT 2025 , Edited by admin on Mon Mar 31 18:12:57 GMT 2025
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TARGET -> INHIBITOR |
BINDING
IC50
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LABELED -> NON-LABELED |
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TARGET -> INHIBITOR |
IC50
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ACTIVE MOIETY |
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