Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H18N6O4 |
| Molecular Weight | 358.3519 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(NC2=CC=CC=C2)=NC3=C1N=CN3[C@@H]4O[C@H](CO)[C@@H](O)[C@H]4O
InChI
InChIKey=SCNILGOVBBRMBK-SDBHATRESA-N
InChI=1S/C16H18N6O4/c17-13-10-14(21-16(20-13)19-8-4-2-1-3-5-8)22(7-18-10)15-12(25)11(24)9(6-23)26-15/h1-5,7,9,11-12,15,23-25H,6H2,(H3,17,19,20,21)/t9-,11-,12-,15-/m1/s1
| Molecular Formula | C16H18N6O4 |
| Molecular Weight | 358.3519 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
2-Phenylaminoadenosine (CV-1808) is an adenosine A2 receptor agonist. CV-1808 is a coronary vasodilator, antihypertensive and antipsychotic following systemic administration in vivo. CV-1808 appeared to be effective for salvaging ischemic myocardium. The effect might be related to improvement of coronary circulation and inhibition of release of vasoactive substances, including TXA2, from the ischemic myocardium. Development of CV-1808 has been discontinued in the United States.
CNS Activity
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Characterization of purine receptors in fetal lamb pulmonary circulation. | 2000-01 |
|
| Differences in the order of potency for agonists but not antagonists at human and rat adenosine A2A receptors. | 1999-01-01 |
|
| Characterization of human A2A adenosine receptors with the antagonist radioligand [3H]-SCH 58261. | 1997-06 |
|
| Further confirmation of the role of adenyl cyclase and of cAMP-dependent protein kinase in primary afferent hyperalgesia. | 1991 |
|
| Hemodynamic effects of adenosine agonists in the conscious spontaneously hypertensive rat. | 1990-09 |
|
| [3H]CGS 21680, a selective A2 adenosine receptor agonist directly labels A2 receptors in rat brain. | 1989-12 |
|
| Adenosine A1 receptor activation mediates suppression of (-) bicuculline methiodide-induced seizures in rat prepiriform cortex. | 1989-12 |
|
| A selective binding site for 3H-NECA that is not an adenosine A2 receptor. | 1989-11-01 |
|
| CGS 21680C, an A2 selective adenosine receptor agonist with preferential hypotensive activity. | 1989-10 |
|
| Effects of adenosine A2 receptor agonists on nucleoside transport. | 1989-10 |
|
| Two phases of contractile response in rat isolated vas deferens and their regulation by adenosine and alpha-receptors. | 1989-08-29 |
|
| An unusual receptor mediates adenosine-induced SA nodal bradycardia in dogs. | 1989-06 |
|
| NECA-induced hypomotility in mice: evidence for a predominantly central site of action. | 1989-02 |
|
| Effect of selective agonists and antagonists on atrial adenosine receptors and their interaction with Bay K 8644 and [3H]-nitrendipine. | 1989-02 |
|
| Comparison of the behavioral effects of adenosine agonists and dopamine antagonists in mice. | 1989 |
|
| Correlation between binding affinities for brain A1 and A2 receptors of adenosine agonists and antagonists and their effects on heart rate and coronary vascular tone. | 1988-12 |
|
| Identification of A1 and A2 adenosine receptors in the rat spinal cord. | 1987-09 |
|
| Definition of subclasses of adenosine receptors associated with adenylate cyclase: interaction of adenosine analogs with inhibitory A1 receptors and stimulatory A2 receptors. | 1987-03 |
|
| Characterization of the A2 adenosine receptor labeled by [3H]NECA in rat striatal membranes. | 1986-04 |
|
| Inhibition of coronary circulatory failure and thromboxane A2 release during coronary occlusion and reperfusion by 2-phenylaminoadenosine (CV-1808) in anesthetized dogs. | 1984-05-01 |
|
| Potentiation of the negative chronotropic and inotropic effects of adenosine by 2-phenylaminoadenosine. | 1983-01-01 |
|
| Interaction of 2-phenylaminoadenosine (CV 1808) with adenosine systems in rat tissues. | 1982-12-03 |
|
| Quantitation of 6-amino-2-phenylamino-9-beta-D-ribofuranosyl-9-H-purine (CV-1808) and its metabolite, 2-(2-hydroxyphenyl)aminoadenosine, in human serum and urine by high performance liquid chromatography using a fluorimetric detector. | 1982-11 |
|
| Effect of 2-phenylaminoadenosine (CV-1808) on ischemic ST-segment elevation in anesthetized dogs. | 1981-11-01 |
|
| Coronary and cardiohemodynamic effects of 2-phenylamino-adenosine (CV-1808) in anesthetized dogs and cats. | 1980 |
Sample Use Guides
Dogs: 2-Phenylaminoadenosine (0.25 ug/kg/min i.v. infusion throughout the experimental period, starting 10 min before coronary occlusion) inhibited coronary circulatory failure and TXA2 release.
Route of Administration:
Intravenous
In Vitro Use Guide
Curator's Comment: A2 receptor activation was measured by the ability of the adenosine agonists to relax porcine coronary smooth muscle. Nucleoside transport was measured as the nitrobenzylthioinosine-sensitive cellular accumulation of [3H]uridine into guinea pig erythrocytes at 22 degrees C.
CV-1808 (2-phenylaminoadenosine) inhibited nucleoside transport with an EC50 of 140 nM.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:59:48 GMT 2025
by
admin
on
Mon Mar 31 18:59:48 GMT 2025
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| Record UNII |
K40I59G1EF
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| Record Status |
Validated (UNII)
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| Record Version |
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C026708
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DTXSID70967878
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6917803
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K40I59G1EF
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