2-PHENYLAMINOADENOSINE

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

Structure Search

SMILES

NC1=C2N=CN([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C2=NC(NC4=CC=CC=C4)=N1

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8105493 | https://www.ncbi.nlm.nih.gov/pubmed/6202970

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adenosine A2a receptor 30 Target ID: CHEMBL251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2016707 \| https://www.ncbi.nlm.nih.gov/pubmed/9179373 \| https://www.ncbi.nlm.nih.gov/pubmed/9920286 \| https://www.ncbi.nlm.nih.gov/pubmed/2795469	Agonist 2678		76.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Schizophrenia 298 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8105493	Primary		Preclinical	Unknown Approved Use Unknown
Coronary heart disease 41 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6202970 http://adisinsight.springer.com/drugs/800002475 https://www.ncbi.nlm.nih.gov/pubmed/6173517	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Coronary and cardiohemodynamic effects of 2-phenylamino-adenosine (CV-1808) in anesthetized dogs and cats.	1980	7191290
Effect of 2-phenylaminoadenosine (CV-1808) on ischemic ST-segment elevation in anesthetized dogs.	1981 Nov-Dec	6173517
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 Nov	7165879
Inhibition of coronary circulatory failure and thromboxane A2 release during coronary occlusion and reperfusion by 2-phenylaminoadenosine (CV-1808) in anesthetized dogs.	1984 May-Jun	6202970
Characterization of the A2 adenosine receptor labeled by [3H]NECA in rat striatal membranes.	1986 Apr	3010074
Definition of subclasses of adenosine receptors associated with adenylate cyclase: interaction of adenosine analogs with inhibitory A1 receptors and stimulatory A2 receptors.	1987 Mar	3580959
Identification of A1 and A2 adenosine receptors in the rat spinal cord.	1987 Sep	3656118
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 Dec	2849674
CGS 21680C, an A2 selective adenosine receptor agonist with preferential hypotensive activity.	1989 Oct	2795469
Effects of adenosine A2 receptor agonists on nucleoside transport.	1989 Oct	2795461
Characterization of human A2A adenosine receptors with the antagonist radioligand [3H]-SCH 58261.	1997 Jun	9179373
Differences in the order of potency for agonists but not antagonists at human and rat adenosine A2A receptors.	1999 Jan 1	9920286
Characterization of purine receptors in fetal lamb pulmonary circulation.	2000 Jan	10625091

Patents

Sample Use Guides

In Vivo Use Guide

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

CV-1808 (2-phenylaminoadenosine) inhibited nucleoside transport with an EC50 of 140 nM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:59:27 GMT 2023` Edited by `admin` on `Fri Dec 15 17:59:27 GMT 2023`
Record UNII	K40I59G1EF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2-PHENYLAMINOADENOSINE

Systematic Name

English

CV-1808

Code

English

ADENOSINE, 2-PHENYLAMINO

Common Name

English

2-PHENYLAMINO ADENOSINE

Systematic Name

English

CV 1808

Code

English

Code System Code Type Description

CAS

53296-10-9