| Identification | Back Directory | [Name]
CCPA | [CAS]
37739-05-2 | [Synonyms]
CCPA
CCPA USP/EP/BP
2-Chloro-N-cyclop
2-CHLORO-N-CYCLOPENTYLADENOSINE
2-chloro-n-cyclopentyl-adenosin
N-Cyclopentyl-2-chloroadenosine
2-CHLORO-N6-CYCLOPENTYLADENOSINE
Adenosine, 2-chloro-N-cyclopentyl-
2-chloro-N(sup 6)-cyclopentyladenosine
2-Chloro-N6-cyclopentyladenosine hemihydrate
2-Chloro-N≤sup>=6≤/sup>=-cyclopentyladenosine
2-CHLORO-N6-CYCLOPENTYLADENOSINE (CCPA) A1 ADENOSINE RECEPTOR
(2R,3R,4S,5R)-2-[2-Chloro-6-(cyclopentylamino)-9H-purin-9-yl]-5-(hydroxymethyl)tetrahydrofuran-3,4-diol | [Molecular Formula]
C15H20ClN5O4 | [MDL Number]
MFCD00078574 | [MOL File]
37739-05-2.mol | [Molecular Weight]
369.8 |
| Chemical Properties | Back Directory | [Boiling point ]
656.1±65.0 °C(Predicted) | [density ]
1.87±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
H2O: 1.7 mg/mL, insoluble | [form ]
solid | [pka]
13.06±0.70(Predicted) | [color ]
off-white to light yellow | [InChI]
1S/C15H20ClN5O4/c16-15-19-12(18-7-3-1-2-4-7)9-13(20-15)21(6-17-9)14-11(24)10(23)8(5-22)25-14/h6-8,10-11,14,22-24H,1-5H2,(H,18,19,20)/t8-,10-,11-,14-/m1/s1 | [InChIKey]
XSMYYYQVWPZWIZ-IDTAVKCVSA-N | [SMILES]
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(NC4CCCC4)nc(Cl)nc23 |
| Safety Data | Back Directory | [Safety Statements ]
24/25 | [WGK Germany ]
3 | [RTECS ]
AU7357555 | [HS Code ]
29349990 | [Storage Class]
11 - Combustible Solids | [Toxicity]
mouse,LD,intraperitoneal,> 100mg/kg (100mg/kg),BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY),Arzneimittel-Forschung. Drug Research. Vol. 44, Pg. 1305, 1994. |
| Hazard Information | Back Directory | [Chemical Properties]
Solid | [Uses]
2-Chloro-N6-cyclopentyl Adenosine is a selective adenosine receptor agonist (1,2). It inhibits angiotensin II induced cardiomyocyte hypertrophy via the calcineurin signaling pathway (2). | [Uses]
2-Chloro-N6-cyclopentyladenosine (CCPA) may be used as an A1 adenosine receptor agonist with high selectivity. CCPA is often used with other adenosine receptor agonists and antagonist to resolve A(1), A(2A) and A(3) receptor functions. These include DPCPX (A(1) receptor antagonist), 4-(2-[7-amino-2-(2-furyl)[1,2,4]triazolo[2,3-α][1,3,5]triazin-5-ylamino]ethyl)phenol (A(2A) receptor antagonist), and 4-[2-[[6-amino-9-(N-ethyl-β-D-ribofuranuronamidosyl)-9H-purin-2-yl]amino]ethyl]benzenepropanoic acid hydrochloride (A(2A) receptor agonist), and Cl-IB-MECA, (A(3)) receptor agonist). | [Uses]
Adenosine receptors are for treating central nervous system (CNS) disorders.
Adenosine A1 receptor agonists include e.g. CCPA, 8-cyclopentyl-1,3-dipropylxanthine, R-phenylisopropyl adenosine. A2A rec
eptor agonists include e.g. regadenoson (Lexiscan), apadenoson, binodenoson. | [Biological Activity]
Potent and selective adenosine A 1 receptor agonist (K i values are 0.8, 2300 and 42 nM for human A 1 , A 2A and A 3 receptors respectively; EC 50 = 18800 nM for hA 2B ). Centrally active following systemic administration in vivo . | [Biochem/physiol Actions]
A1 adenosine receptor agonist with high selectivity: reportedly 10,000-fold for A1 over A2 receptors. | [storage]
Desiccate at RT | [References]
[1]. lohse mj, klotz kn, schwabe u, et al. 2-chloro-n6-cyclopentyladenosine: a highly selective agonist at a1 adenosine receptors. naunyn schmiedebergs arch pharmacol, 1988, 337(6): 687-689.
[2]. monopoli a, conti a, dionisotti s, et al. pharmacology of the highly selective a1 adenosine receptor agonist 2-chloro-n6-cyclopentyladenosine. arzneimittelforschung, 1994, 44(12): 1305-1312.
[3]. concas a, santoro g, mascia mp, et al. anticonvulsant doses of 2-chloro-n6-cyclopentyladenosine, an adenosine a1 receptor agonist, reduce gabaergic transmission in different areas of the mouse brain. j pharmacol exp ther, 1993, 267(2): 844-851.
[4]. sandoli d, chiu pj, chintala m, et al. in vivo and ex vivo effects of adenosine a1 and a2 receptor agonists on platelet aggregation in the rabbit. eur j pharmacol, 1994, 259(1): 43-49. |
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