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 |
|---|---|---|
| Epileptogenic action of caffeine during anoxia in the neonatal rat hippocampus. | 1999 Jul |
|
| Estradiol inhibits smooth muscle cell growth in part by activating the cAMP-adenosine pathway. | 2000 Jan |
|
| 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 |
|
| 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 |
|
| [(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 |
|
| A functional role for adenosine A3 receptors: modulation of synaptic plasticity in the rat hippocampus. | 2001 Apr 13 |
|
| 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 |
|
| Distinct modulation of evoked and spontaneous EPSCs by purinoceptors in the nucleus tractus solitarii of the rat. | 2001 Feb 1 |
|
| Adenosine A1 receptors regulate the response of the hamster circadian clock to light. | 2001 Feb 23 |
|
| K(ATP) channel blockers selectively interact with A(1)-adenosine receptor mediated modulation of acetylcholine release in the rat hippocampus. | 2001 Jan 19 |
|
| Inhibition of calcium channels by opioid- and adenosine-receptor agonists in neurons of the nucleus accumbens. | 2001 Jun |
|
| Adenosine A(1) receptor-mediated inhibition of protein kinase A-induced calcitonin gene-related peptide release from rat trigeminal neurons. | 2001 Jun |
|
| Agonist-stimulated [35S]GTPgammaS autoradiography: optimization for high sensitivity. | 2001 Jun 22 |
|
| Adenosine inhibits norepinephrine release in the postischemic rat heart: the mechanism of neuronal stunning. | 2001 Mar |
|
| Adenosine enhances neuroexcitability by inhibiting a slow postspike afterhyperpolarization in rabbit vagal afferent neurons. | 2001 Mar 6 |
|
| Electrically evoked release of glutamate in rat hippocampal slices: effects of various drugs and fimbria-fornix lesions. | 2001 May |
|
| 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 |
|
| Anti-adrenergic effect of adenosine on Na(+)-Ca(2+) exchange current recorded from guinea-pig ventricular myocytes. | 2001 May |
|
| Mechanism of intracellular calcium ([Ca2+]i) inhibition of lipolysis in human adipocytes. | 2001 Nov |
|
| Acute and chronic caffeine administration differentially alters striatal gene expression in wild-type and adenosine A(2A) receptor-deficient mice. | 2001 Nov |
|
| 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 |
|
| Adenosine linking reduced O2 to arteriolar NO release in intestine is not formed from extracellular ATP. | 2001 Sep |
|
| 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 |
|
| PDE7A is expressed in human B-lymphocytes and is up-regulated by elevation of intracellular cAMP. | 2002 Mar |
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
Fri Dec 15 15:54:42 GMT 2023
by
admin
on
Fri Dec 15 15:54:42 GMT 2023
|
| Record UNII |
9PTP4FOI9E
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Systematic Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
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 | ||
|---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
|
