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Compound Detail

CHEMBL13852

CIRAZOLINE
🧪 Phase II
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🧪 Phase II
c1ccc(C2CC2)c(OCC2=NCCN2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL13852
Name CIRAZOLINE
Phase Phase II
Structure Type MOL
InChI Key YAORIDZYZDUZCM-UHFFFAOYSA-N

Known Names

Cirazolina Cirazoline Ld-3098
12
Targets
32
Activities
3
Assay Types
0
PK Parameters
20
Publications
3
Known Names

Molecular Properties

216.3
MW (Da)
1.94
ALogP
3
HBA
1
HBD
33.6
PSA (Ų)
0.83
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Achiral

Flags

Natural Product
USAN Stem -azoline

Extended Properties

Molecular Formula C13H16N2O
MW 216.28
Aromatic Rings 1
Heavy Atoms 16
NP-Likeness -0.28

Activity Summary

EC50 16 meas. best 7.9
Ki 14 meas. best 8.41
IC50 2 meas. best 7.23

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 Ki 8.41 7.7267 3.9 3
Nischarin
CHEMBL3923
 Ki 8.4 7.4667 4.0 3
Alpha-1A adrenergic receptor
CHEMBL229
 EC50 7.9 7.9 12.6 4
5-hydroxytryptamine receptor 1A
CHEMBL214
 Ki 7.46 7.46 34.7 1
Alpha-2A adrenergic receptor
CHEMBL1867
 Ki 7.23 7.23 58.9 2
Adrenergic receptor alpha-2
CHEMBL2093864
 IC50 7.23 7.23 59.0 1
Alpha-1B adrenergic receptor
CHEMBL232
 EC50 7.2 7.2 63.1 4
Alpha-1D adrenergic receptor
CHEMBL223
 EC50 6.9 6.9 125.9 4
Alpha-2C adrenergic receptor
CHEMBL1916
 EC50 6.4 6.4 398.1 2
Alpha-2B adrenergic receptor
CHEMBL1942
 Ki 6.28 6.28 524.8 2
Alpha-2C adrenergic receptor
CHEMBL1916
 Ki 6.26 6.26 549.5 2
Adrenergic receptor alpha-1
CHEMBL1907610
 IC50 6.05 6.05 890.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
 EC50 6.0 6.0 1000.0 2
Nischarin
CHEMBL5221
 Ki 5.76 5.76 1737.8 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 3.89 nM 8.41 Binding affinity to I2 imidazoline binding site (unknown origin) -
Nischarin Ki = 3.981 nM 8.4 Binding affinity for imidazoline receptor I-2 in rabbit kidney homogenate (relat... 10737743
Unchecked Ki = 4.467 nM 8.35 Binding affinity to I2 imidazoline binding site in rat brain membrane 24900763
Alpha-1A adrenergic receptor EC50 = 12.59 nM 7.9 Activation of recombinant human adrenergic,alpha-1A receptor expressed in rat-1 ... 11814822
Alpha-1A adrenergic receptor EC50 = 12.59 nM 7.9 In vitro activation of human alpha-1A receptor expressed in rat-1 fibroblasts vi... 11844675
Alpha-1A adrenergic receptor EC50 = 12.59 nM 7.9 Activation of human alpha-1A adrenergic receptor expressed in rat-1 fibroblasts 12419381
Alpha-1A adrenergic receptor EC50 = 12.59 nM 7.9 Agonist potency against cloned human alpha 1A adrenoceptor expressed in rat-1 fi... 11597419
5-hydroxytryptamine receptor 1A Ki = 34.67 nM 7.46 Binding affinity at human 5HT1A receptor 24900763
Adrenergic receptor alpha-2 IC50 = 59.0 nM 7.23 Binding affinity against Alpha-2 adrenergic receptor is the ability to inhibit t... 6142954
Alpha-2A adrenergic receptor Ki = 58.88 nM 7.23 Binding affinity at human alpha2A AR 24900763
Alpha-2A adrenergic receptor Ki = 58.88 nM 7.23 Displacement of [3H]RX821002 from human alpha2A adrenoceptor expressed in CHO ce... 19886609
Alpha-1B adrenergic receptor EC50 = 63.1 nM 7.2 Potency against cloned human alpha 1B adrenoceptor expressed in rat-1 fibroblast... 11597419
Alpha-1B adrenergic receptor EC50 = 63.1 nM 7.2 Activation of human alpha-1B adrenergic receptors expressed in rat-1 fibroblasts 12419381
Alpha-1B adrenergic receptor EC50 = 63.1 nM 7.2 In vitro activation of human Alpha-1B receptor expressed in rat-1 fibroblasts vi... 11844675
Alpha-1B adrenergic receptor EC50 = 63.1 nM 7.2 Activation of recombinant human adrenergic, alpha-1B receptor expressed in rat-1... 11814822
Nischarin Ki = 99.0 nM 7.0 Displacement of [125I]PIC from human imidazoline receptor 1 in human platelets a... 18621536
Nischarin Ki = 99.08 nM 7.0 Displacement of [125I]PIC from human imidazoline receptor 1 in human platelets a... 18621536
Alpha-1D adrenergic receptor EC50 = 125.89 nM 6.9 Activation of human Alpha-1D adrenergic receptors expressed in rat-1 fibroblasts 12419381
Alpha-1D adrenergic receptor EC50 = 125.89 nM 6.9 In vitro activation of human alpha-1D receptor expressed in rat-1 fibroblasts vi... 11844675
Alpha-1D adrenergic receptor EC50 = 125.89 nM 6.9 Activation of recombinant human adrenergic, alpha-1D receptor expressed in rat-1... 11814822

Literature References

PubMed DOI Target Context # Activities
19886609 10.1021/jm901262f Alpha-2B adrenergic receptor 3
2993616 10.1021/jm00147a026 Rattus norvegicus 3
19886609 10.1021/jm901262f Alpha-2C adrenergic receptor 3
11814822 10.1016/s0960-894x(01)00764-8 Alpha-1D adrenergic receptor 2
18621536 10.1016/j.bmc.2008.06.051 Unchecked 2
18621536 10.1016/j.bmc.2008.06.051 Nischarin 2
12419381 10.1016/s0960-894x(02)00753-9 Alpha-1D adrenergic receptor 2
12419381 10.1016/s0960-894x(02)00753-9 Alpha-1B adrenergic receptor 2
12419381 10.1016/s0960-894x(02)00753-9 Alpha-1A adrenergic receptor 2
19886609 10.1021/jm901262f Alpha-2A adrenergic receptor 2
24900763 10.1021/ml400232p 5-hydroxytryptamine receptor 1A 2
24900763 10.1021/ml400232p Alpha-2B adrenergic receptor 2
11814822 10.1016/s0960-894x(01)00764-8 Alpha-1B adrenergic receptor 2
11814822 10.1016/s0960-894x(01)00764-8 Alpha-1A adrenergic receptor 2
11597419 10.1016/s0960-894x(01)00569-8 Alpha-1D adrenergic receptor 2
11597419 10.1016/s0960-894x(01)00569-8 Alpha-1B adrenergic receptor 2
11597419 10.1016/s0960-894x(01)00569-8 Alpha-1A adrenergic receptor 2
24900763 10.1021/ml400232p Alpha-2A adrenergic receptor 2
24900763 10.1021/ml400232p Alpha-2C adrenergic receptor 2
11844675 10.1016/s0960-894x(01)00822-8 Alpha-1A adrenergic receptor 1

Data from ChEMBL 36 via Core Engine