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Compound Detail

CHEMBL2105747

TOZADENANT
🧪 Phase III
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🧪 Phase III
COc1ccc(N2CCOCC2)c2sc(NC(=O)N3CCC(C)(O)CC3)nc12
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2105747
Name TOZADENANT
Phase Phase III
Structure Type MOL
InChI Key XNBRWUQWSKXMPW-UHFFFAOYSA-N

Known Names

A-2A (3) A2A (3) A2A-(3) RO-4494351 RO-4494351-000 RO-4494351-002 RO-4494351000 RO4494351 RO4494351-000 RO4494351-002 SYN-115 SYN115 +1 more
5
Targets
21
Activities
1
Assay Types
10
PK Parameters
20
Publications
13
Known Names
3
Indications
1
Mechanisms

Molecular Properties

406.5
MW (Da)
2.52
ALogP
7
HBA
2
HBD
87.2
PSA (Ų)
0.81
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -adenant
USAN Year 2011

Extended Properties

Molecular Formula C19H26N4O4S
MW 406.51
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -1.42

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Adenosine A2a receptor antagonist ANTAGONIST Adenosine receptor A2a ✓ ✓

Indications

Parkinson Disease Liver Diseases Cocaine-Related Disorders

Activity Summary

Ki 21 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adenosine receptor A2a
CHEMBL251
 Ki 9.52 8.3667 0.3 9
Adenosine receptor A2a
CHEMBL302
 Ki 7.73 7.73 18.7 1
Adenosine receptor A2b
CHEMBL255
 Ki 6.16 5.8733 700.0 3
Adenosine receptor A1
CHEMBL226
 Ki 5.87 5.7333 1350.0 6
Adenosine receptor A3
CHEMBL256
 Ki 5.8 5.55 1570.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 11.0 mL.min-1.kg-1 Rattus norvegicus
CL 8.0 mL.min-1.kg-1 Canis lupus familiaris
Cmax 829.01 nM Mus musculus
F 77.0 % Rattus norvegicus
F 88.0 % Canis lupus familiaris
T1/2 4.0 hr Rattus norvegicus
T1/2 2.2 hr Canis lupus familiaris
T1/2 0.184 hr Mus musculus
Vd 1.4 L.kg-1 Rattus norvegicus
Vd 1.2 L.kg-1 Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adenosine receptor A2a Ki = 0.3 nM 9.52 Antagonist activity at human adenosine A2A receptor expressed in HEK293 cell mem... 28055204
Adenosine receptor A2a Ki = 3.4 nM 8.47 Binding affinity to human adenosine A2A receptor measured by radioligand-based a... 34695776
Adenosine receptor A2a Ki = 3.9 nM 8.41 Displacement of [3H]-ZM241385 from recombinant human A2A receptor expressed in C... 33548636
Adenosine receptor A2a Ki = 5.0 nM 8.3 Inhibition of human recombinant adenosine receptor A2a 24164628
Adenosine receptor A2a Ki = 5.0 nM 8.3 Antagonist activity at human adenosine 2A receptor (409 to 412 residues) express... 32667814
Adenosine receptor A2a Ki = 5.0 nM 8.3 Antagonist activity at adenosine A2A receptor (unknown origin) 34695776
Adenosine receptor A2a Ki = 8.3 nM 8.08 Displacement of [3H]MSX2 from human adenosine receptor A2A expressed in HEK293 c... 31780082
Adenosine receptor A2a Ki = 11.0 nM 7.96 Displacement of [3H]ZM241385 from human adenosine A2A receptor expressed in HEK2... 28055204
Adenosine receptor A2a Ki = 11.0 nM 7.96 Antagonist activity at human adenosine A2A receptor 35462165
Adenosine receptor A2a Ki = 18.7 nM 7.73 Displacement of [3H]-ZM241385 from A2A receptor in rat brain corpora striata inc... 33548636
Adenosine receptor A2b Ki = 700.0 nM 6.16 Inhibition of human recombinant adenosine receptor A2b 24164628
Adenosine receptor A2b Ki = 700.0 nM 6.16 Inhibition of human adenosine 2B receptor 32667814
Adenosine receptor A1 Ki = 1350.0 nM 5.87 Inhibition of human recombinant adenosine A1 receptor 24164628
Adenosine receptor A1 Ki = 1350.0 nM 5.87 Inhibition of human adenosine A1 receptor 32667814
Adenosine receptor A3 Ki = 1570.0 nM 5.8 Inhibition of human recombinant adenosine A3 receptor 24164628
Adenosine receptor A1 Ki = 1700.0 nM 5.77 Displacement of [3H]-DPCPX from human adenosine A1 receptor expressed in HEK293 ... 28055204
Adenosine receptor A1 Ki = 1700.0 nM 5.77 Antagonist activity at human adenosine A1 receptor 35462165
Adenosine receptor A1 Ki = 2240.0 nM 5.65 Displacement of [3H]CCPA from human adenosine receptor A1 expressed in CHO cell ... 31780082
Adenosine receptor A1 Ki = 3380.0 nM 5.47 Displacement of [3H]-DPCPX from recombinant human A1 receptor expressed in CHO-K... 33548636
Adenosine receptor A2b Ki = 5000.0 nM 5.3 Displacement of [3H]-MRS-1754 from human adenosine A2B receptor expressed in HEK... 28055204

Literature References

PubMed DOI Target Context # Activities
24164628 10.1021/jm4011669 Rattus norvegicus 4
24164628 10.1021/jm4011669 Canis familiaris 4
32667814 10.1021/acs.jmedchem.0c00237 ADMET 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
33548636 10.1016/j.ejmech.2021.113214 Adenosine receptor A2a 2
34695776 10.1016/j.ejmech.2021.113907 Adenosine receptor A2a 2
28055204 10.1021/acs.jmedchem.6b01584 Adenosine receptor A2a 2
28055204 10.1021/acs.jmedchem.6b01584 Adenosine receptor A1 2
28055204 10.1021/acs.jmedchem.6b01584 Adenosine receptor A2b 2
24164628 10.1021/jm4011669 Unchecked 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
28055204 10.1021/acs.jmedchem.6b01584 Adenosine receptor A3 1
- 10.21203/rs.3.rs-23951/v1 SARS-CoV-2 1
35462165 10.1016/j.ejmech.2022.114378 Adenosine receptor A1 1
28055204 10.1021/acs.jmedchem.6b01584 Cytochrome P450 2C19 1
28055204 10.1021/acs.jmedchem.6b01584 Cytochrome P450 2C9 1
28055204 10.1021/acs.jmedchem.6b01584 Rattus norvegicus 1
28055204 10.1021/acs.jmedchem.6b01584 Cytochrome P450 1A2 1
24164628 10.1021/jm4011669 Adenosine receptor A1 1
24164628 10.1021/jm4011669 Adenosine receptor A2a 1

Data from ChEMBL 36 via Core Engine