Lexiscan (CED0006393)

Record Information

Version

1.0

Creation Date

2016-05-22 07:20:49 UTC

Update Date

2026-08-19 11:03:18 UTC

Accession Number

CHEM020710

Identification

Common Name

Lexiscan

Class

Small Molecule

Description

Lexiscan is an organic compound with the formula C15H18N8O5 and an average molecular weight of 390.35 g/mol. Lexiscan belongs to the purine nucleosides, a class of nucleosides, nucleotides, and analogues within the organic compounds. The substance is found in or released from three recorded sources, which include cardiac preparations within healthcare, pharmaceuticals, and veterinary products, as well as television systems and antennas within electrical and electronic equipment. The recorded route of exposure for this compound is intravenous. In terms of biological activity, Lexiscan has one recorded protein target, acting as an agonist of the adenosine receptor A2a (ADORA2A).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Lexiscan	Kegg
1-{6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-2-yl}-N-methyl-1H-pyrazole-4-carboximidate	Generator

Chemical Formula

C₁₅H₁₈N₈O₅

Average Molecular Mass

390.354 g/mol

Monoisotopic Mass

390.140 g/mol

CAS Registry Number

313348-27-5

IUPAC Name

1-{6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-9H-purin-2-yl}-N-methyl-1H-pyrazole-4-carboxamide

Traditional Name

regadenoson

SMILES

CNC(=O)C1=CN(N=C1)C1=NC2=C(N=CN2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)C(N)=N1

InChI Identifier

InChI=1S/C15H18N8O5/c1-17-13(27)6-2-19-23(3-6)15-20-11(16)8-12(21-15)22(5-18-8)14-10(26)9(25)7(4-24)28-14/h2-3,5,7,9-10,14,24-26H,4H2,1H3,(H,17,27)(H2,16,20,21)/t7-,9-,10-,14-/m1/s1

InChI Key

LZPZPHGJDAGEJZ-AKAIJSEGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleosides

Sub Class

Not Available

Direct Parent

Purine nucleosides

Alternative Parents

Substituents

Purine nucleoside
Glycosyl compound
N-glycosyl compound
6-aminopurine
Pentose monosaccharide
Imidazopyrimidine
Purine
Pyrazole-4-carboxamide
Aminopyrimidine
Monosaccharide
N-substituted imidazole
Imidolactam
Pyrimidine
Azole
Imidazole
Heteroaromatic compound
Vinylogous amide
Pyrazole
Tetrahydrofuran
Secondary carboxylic acid amide
Secondary alcohol
Amino acid or derivatives
Carboxamide group
Azacycle
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Primary amine
Alcohol
Organic oxide
Organopnictogen compound
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.85 g/L	ALOGPS
logP	-0.89	ALOGPS
logP	-2.3	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	1.63	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	186.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.48 m³·mol⁻¹	ChemAxon
Polarizability	37.48 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0095000000-da650c0d5369ec8b71ae	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-2090000000-8f4b2f74d1b6e5dfb3bf	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zfr-0090000000-b8e03ad5fc14c7a898fa	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052r-0159000000-fed68aaf4ee7c4aa91bd	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-1690000000-38161bf0f7e21d763c4a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0abc-4980000000-7c8006c697803ba0bfef	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2454.0	Log mg/kg	[1400:4400]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
288	Cardiac preparations	Healthcare, pharmaceuticals & veterinary products	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available

Pathways

2 pathways

Regadenoson Drug Metabolism

Regadenoson Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	5-hydroxytryptamine receptor 2A	P28223	Humans	Predicted (SEA)	83.6101
Click to view 3D structure	CD99 antigen	P14209	Humans	Predicted (SEA)	1.16774
Click to view 3D structure	Adenosine receptor A1	P28190	Bos taurus	Predicted (SEA)	17.1268
Click to view 3D structure	High affinity choline transporter 1	Q9GZV3	Humans	Predicted (SEA)	5.52729
Click to view 3D structure	NAD kinase	Q5HH78	Staphylococcus aureus (strain COL)	Predicted (SEA)	4.5931
Click to view 3D structure	NAD kinase 1	Q8Y8D7	Listeria monocytogenes serovar 1/2a (strain ATCC BAA-679 / EGD-e)	Predicted (SEA)	4.5931
Click to view 3D structure	P2Y purinoceptor 1	P47900	Humans	Predicted (SEA)	14.8692
Click to view 3D structure	Adenosine deaminase	P56658	Bos taurus	Predicted (SEA)	4.67095
Click to view 3D structure	P2Y purinoceptor 1	P49651	Rattus norvegicus	Predicted (SEA)	7.08428
Click to view 3D structure	Adenosine receptor A2a	P46616	Cavia porcellus	Predicted (SEA)	11.2103
Click to view 3D structure	P2Y purinoceptor 1	P49652	Meleagris gallopavo	Predicted (SEA)	11.2103
Click to view 3D structure	Serine--tRNA ligase	P95689	Staphylococcus aureus (strain NCTC 8325 / PS 47)	Predicted (SEA)	4.20386
Click to view 3D structure	Adenosine receptor A3	Q61618	Mus musculus	Predicted (SEA)	17.7496
Click to view 3D structure	Adenosine receptor A1	Q60612	Mus musculus	Predicted (SEA)	17.8275
Click to view 3D structure	P2X purinoceptor 3	P56373	Humans	Predicted (SEA)	12.378
Click to view 3D structure	Adenosine receptor A2a	P30543	Rattus norvegicus	Predicted (SEA)	7.00643
Click to view 3D structure	Adenosine receptor A2a	P29274	Humans	Predicted (SEA)	10.6653
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	22.4206
Click to view 3D structure	Adenosine receptor A1	P30542	Humans	Predicted (SEA)	23.5883
Click to view 3D structure	Adenosine receptor A1	P25099	Rattus norvegicus	Predicted (SEA)	23.9776
Click to view 3D structure	Adenosine receptor A3	P28647	Rattus norvegicus	Predicted (SEA)	15.2584
Click to view 3D structure	Heat shock protein HSP 90-alpha	P07900	Humans	Predicted (SEA)	9.809
Click to view 3D structure	Endoplasmin	P14625	Humans	Predicted (SEA)	7.55137
Click to view 3D structure	Adenosine receptor A1	P47745	Cavia porcellus	Predicted (SEA)	7.16213
Click to view 3D structure	Adenosine receptor A2b	P29275	Humans	Predicted (SEA)	31.7625