Dipropilciklopentilksantin

Dipropilciklopentilksantin
(IUPAC) ime
	8-ciklopentil-1,3-dipropil-7H-purin-2,6-dion
Klinički podaci
Identifikatori
CAS broj	102146-07-6
ATC kod	nije dodeljen
PubChem	1329
ChemSpider	1289
ChEMBL	CHEMBL183
Hemijski podaci
Formula	C16H24N4O2
Mol. masa	304,386 g/mol
SMILES	eMolekuli & PubHem
InChI
	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) ; Key: FFBDFADSZUINTG-UHFFFAOYSA-N
Fizički podaci
Tačka topljenja	191–194 °C (376–381 °F)
Farmakoinformacioni podaci
Trudnoća	?
Pravni status	Uncontrolled

8-Ciklopentil-1,3-dipropilksantin (DPCPX, PD-116,948) je lek koji deluje kao potentan i selektivan antagonist adenozinskog A₁ receptora.^[5]^[6] On je visoko selektivan za A₁ u odnosu na druge tipove adenozinskog receptora, ali poput drugih derivata ksantina on takođe deluje kao inhibitor fosfodiesteraze, i skoro je jednako potentan kao i rolipram u inhibiranju PDE4.^[7] On se koristi za studiranje funkcije adenozinskog A₁ receptora kod životinja.^[8]^[9] Utvrđeno je da učestvuje u više važnih funkcija kao što su regulacija disanja^[10] i da je aktivan u različitim regionima mozga.^[11]^[12] Za DPCPX je takođe pokazano da proizvodi bihaviouralne efekte, kao što je povišenje halucinogenih odgovora proizvedenih dejstvom 5-HT_2A agonista DOI,^[13] i otpuštanje dopamina indukovanog MDMA-om,^[14] kao i da formira interakcije sa brojnim antikonvulzivnim lekovima.^[15]^[16]

Reference

↑ Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit
↑ Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.
↑ Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit
↑ Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit
↑ Martinson EA, Johnson RA, Wells JN (March 1987). „Potent adenosine receptor antagonists that are selective for the A1 receptor subtype”. Molecular Pharmacology 31 (3): 247–52. PMID 3561384. ^{[mrtav link]}
↑ Lohse MJ, Klotz KN, Lindenborn-Fotinos J, Reddington M, Schwabe U, Olsson RA (August 1987). „8-Cyclopentyl-1,3-dipropylxanthine (DPCPX)--a selective high affinity antagonist radioligand for A1 adenosine receptors”. Naunyn-Schmiedeberg's Archives of Pharmacology 336 (2): 204–10. DOI:10.1007/BF00165806. PMID 2825043.
↑ Ukena D, Schudt C, Sybrecht GW (February 1993). „Adenosine receptor-blocking xanthines as inhibitors of phosphodiesterase isozymes”. Biochemical Pharmacology 45 (4): 847–51. DOI:10.1016/0006-2952(93)90168-V. PMID 7680859.
↑ Coates J, Sheehan MJ, Strong P (May 1994). „1,3-Dipropyl-8-cyclopentyl xanthine (DPCPX): a useful tool for pharmacologists and physiologists?”. General Pharmacology 25 (3): 387–94. PMID 7926579.
↑ Moro S, Gao ZG, Jacobson KA, Spalluto G (March 2006). „Progress in the pursuit of therapeutic adenosine receptor antagonists”. Medicinal Research Reviews 26 (2): 131–59. DOI:10.1002/med.20048. PMID 16380972.
↑ Vandam RJ, Shields EJ, Kelty JD (2008). „Rhythm generation by the pre-Bötzinger complex in medullary slice and island preparations: effects of adenosine A(1) receptor activation”. BMC Neuroscience 9: 95. DOI:10.1186/1471-2202-9-95. PMC 2567986. PMID 18826652.
↑ Migita H, Kominami K, Higashida M, Maruyama R, Tuchida N, McDonald F, Shimada F, Sakurada K (October 2008). „Activation of adenosine A1 receptor-induced neural stem cell proliferation via MEK/ERK and Akt signaling pathways”. Journal of Neuroscience Research 86 (13): 2820–8. DOI:10.1002/jnr.21742. PMID 18618669.
↑ Wu C, Wong T, Wu X, Sheppy E, Zhang L (February 2009). „Adenosine as an endogenous regulating factor of hippocampal sharp waves”. Hippocampus 19 (2): 205–20. DOI:10.1002/hipo.20497. PMID 18785213.
↑ Marek GJ (March 2009). „Activation of adenosine(1) (A(1)) receptors suppresses head shakes induced by a serotonergic hallucinogen in rats”. Neuropharmacology 56 (8): 1082–7. DOI:10.1016/j.neuropharm.2009.03.005. PMC 2706691. PMID 19324062.
↑ Vanattou-Saïfoudine N, Gossen A, Harkin A (January 2011). „A role for adenosine A(1) receptor blockade in the ability of caffeine to promote MDMA "Ecstasy"-induced striatal dopamine release”. European Journal of Pharmacology 650 (1): 220–8. DOI:10.1016/j.ejphar.2010.10.012. PMID 20951694.
↑ De Sarro G, Donato Di Paola E, Falconi U, Ferreri G, De Sarro A (December 1996). „Repeated treatment with adenosine A1 receptor agonist and antagonist modifies the anticonvulsant properties of CPPene”. European Journal of Pharmacology 317 (2-3): 239–45. DOI:10.1016/S0014-2999(96)00746-7. PMID 8997606.
↑ Chwalczuk K, Rubaj A, Swiader M, Czuczwar SJ (2008). „[Influence of the antagonist of adenosine A1 receptors, 8-cyclopentyl-1 ,3-dipropylxanthine, upon the anticonvulsant activity of antiepileptic drugs in mice]” (Polish). Przegla̧d Lekarski 65 (11): 759–63. PMID 19205356.

Povezano

CPX
Ksantin

Spoljašnje veze

	Portal Medicina
	Portal Hemija

Kategorije

[1] Li Q, Cheng T, Wang Y, Bryant SH (2010). „PubChem as a public resource for drug discovery.”. Drug Discov Today 15 (23-24): 1052-7. DOI:10.1016/j.drudis.2010.10.003. PMID 20970519. edit

[2] Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). „Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities”. Annual Reports in Computational Chemistry 4: 217-241. DOI:10.1016/S1574-1400(08)00012-1.

[3] Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). „Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining”. J Cheminform 2 (1): 3. DOI:10.1186/1758-2946-2-3. PMID 20331846. edit

[4] Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). „ChEMBL: a large-scale bioactivity database for drug discovery”. Nucleic Acids Res 40 (Database issue): D1100-7. DOI:10.1093/nar/gkr777. PMID 21948594. edit

[5] Martinson EA, Johnson RA, Wells JN (March 1987). „Potent adenosine receptor antagonists that are selective for the A1 receptor subtype”. Molecular Pharmacology 31 (3): 247–52. PMID 3561384. ^{[mrtav link]}

[6] Lohse MJ, Klotz KN, Lindenborn-Fotinos J, Reddington M, Schwabe U, Olsson RA (August 1987). „8-Cyclopentyl-1,3-dipropylxanthine (DPCPX)--a selective high affinity antagonist radioligand for A1 adenosine receptors”. Naunyn-Schmiedeberg's Archives of Pharmacology 336 (2): 204–10. DOI:10.1007/BF00165806. PMID 2825043.

[pmid7680859-7] Ukena D, Schudt C, Sybrecht GW (February 1993). „Adenosine receptor-blocking xanthines as inhibitors of phosphodiesterase isozymes”. Biochemical Pharmacology 45 (4): 847–51. DOI:10.1016/0006-2952(93)90168-V. PMID 7680859.

[8] Coates J, Sheehan MJ, Strong P (May 1994). „1,3-Dipropyl-8-cyclopentyl xanthine (DPCPX): a useful tool for pharmacologists and physiologists?”. General Pharmacology 25 (3): 387–94. PMID 7926579.

[9] Moro S, Gao ZG, Jacobson KA, Spalluto G (March 2006). „Progress in the pursuit of therapeutic adenosine receptor antagonists”. Medicinal Research Reviews 26 (2): 131–59. DOI:10.1002/med.20048. PMID 16380972.

[10] Vandam RJ, Shields EJ, Kelty JD (2008). „Rhythm generation by the pre-Bötzinger complex in medullary slice and island preparations: effects of adenosine A(1) receptor activation”. BMC Neuroscience 9: 95. DOI:10.1186/1471-2202-9-95. PMC 2567986. PMID 18826652.

[11] Migita H, Kominami K, Higashida M, Maruyama R, Tuchida N, McDonald F, Shimada F, Sakurada K (October 2008). „Activation of adenosine A1 receptor-induced neural stem cell proliferation via MEK/ERK and Akt signaling pathways”. Journal of Neuroscience Research 86 (13): 2820–8. DOI:10.1002/jnr.21742. PMID 18618669.

[12] Wu C, Wong T, Wu X, Sheppy E, Zhang L (February 2009). „Adenosine as an endogenous regulating factor of hippocampal sharp waves”. Hippocampus 19 (2): 205–20. DOI:10.1002/hipo.20497. PMID 18785213.

[13] Marek GJ (March 2009). „Activation of adenosine(1) (A(1)) receptors suppresses head shakes induced by a serotonergic hallucinogen in rats”. Neuropharmacology 56 (8): 1082–7. DOI:10.1016/j.neuropharm.2009.03.005. PMC 2706691. PMID 19324062.

[pmid20951694-14] Vanattou-Saïfoudine N, Gossen A, Harkin A (January 2011). „A role for adenosine A(1) receptor blockade in the ability of caffeine to promote MDMA "Ecstasy"-induced striatal dopamine release”. European Journal of Pharmacology 650 (1): 220–8. DOI:10.1016/j.ejphar.2010.10.012. PMID 20951694.

[pmid8997606-15] De Sarro G, Donato Di Paola E, Falconi U, Ferreri G, De Sarro A (December 1996). „Repeated treatment with adenosine A1 receptor agonist and antagonist modifies the anticonvulsant properties of CPPene”. European Journal of Pharmacology 317 (2-3): 239–45. DOI:10.1016/S0014-2999(96)00746-7. PMID 8997606.

[pmid19205356-16] Chwalczuk K, Rubaj A, Swiader M, Czuczwar SJ (2008). „[Influence of the antagonist of adenosine A1 receptors, 8-cyclopentyl-1 ,3-dipropylxanthine, upon the anticonvulsant activity of antiepileptic drugs in mice]” (Polish). Przegla̧d Lekarski 65 (11): 759–63. PMID 19205356.

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p r u Inhibitori fosfodiesteraze
PDE1	MMPX • SCH-51866 • Vinpocetin
PDE2	BAY 60-7550 • EHNA
PDE3	Amrinon • Anagrelid • Bukladezin • Cilostamid • Cilostazol • Enoksimon • KMUP-1 • Milrinon • Kvazinon • RPL-554 • Siguazodan • Trekvinsin • Vesnarinon • Zardaverin
PDE4	Arofilin • Cilomilast • CP-80633 • Denbutilin • Drotaverin • Etazolat • Filaminast • Glaucin • HT-0712 • Ibudilast • ICI-63197 • Irsogladin • Luteolin • Mesembrin • Piklamilast • Roflumilast • Rolipram • Ro20-1724 • RPL-554 • YM-976
PDE5	Acetildenafil • Aildenafil • Avanafil • Dipiridamol • Ikariin • Lodenafil • Mirodenafil • MY-5445 • Nitrozoprodenafil • Sildenafil • Sulfoaildenafil • T-0156 • Tadalafil • Udenafil • Vardenafil
PDE6	Zaprinast
PDE7	BRL-50481
PDE9	BAY 73-6691 • SCH-51866
PDE10	Papaverin • PF-2545920 • Tofizopam
Nonselektivni	Kafein • Doksofilin • IBMX • Pentoksifilin • Propentofilin • Teofilin

Dipropilciklopentilksantin

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