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Compound Detail

CHEMBL497939

CYTISINICLINE
🧪 Phase III
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🧪 Phase III
O=c1cccc2n1C[C@@H]1CNC[C@H]2C1

Basic Information

ChEMBL ID CHEMBL497939
Name CYTISINICLINE
Phase Phase III
Structure Type MOL
InChI Key ANJTVLIZGCUXLD-DTWKUNHWSA-N

Known Names

6039 Sopharma Baptitoxine Citisiniclina Cytisine Cytisinicline Cytiton NSC-407282 Sophorine Tabex Ulexine
19
Targets
97
Activities
4
Assay Types
0
PK Parameters
20
Publications
10
Known Names
3
Indications
1
Mechanisms

Molecular Properties

190.2
MW (Da)
0.56
ALogP
3
HBA
1
HBD
34.0
PSA (Ų)
0.65
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Stem -nicline
USAN Year 2018

Extended Properties

Molecular Formula C11H14N2O
MW 190.25
Aromatic Rings 1
Heavy Atoms 14
NP-Likeness -0.21

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Neuronal acetylcholine receptor; alpha4/beta2 partial agonist PARTIAL AGONIST Neuronal acetylcholine receptor; alpha4/beta2

Indications

Smoking Cessation Tobacco Use Disorder Kidney Diseases

ATC Classification

N07BA04
cytisine
Level 1: NERVOUS SYSTEM
Level 2: OTHER NERVOUS SYSTEM DRUGS

Activity Summary

Ki 72 meas. best 9.91
EC50 17 meas. best 9.38
IC50 7 meas. best 7.3
Kd 1 meas. best 9.84

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
Ki 9.91 9.21 0.1 19
Unchecked
CHEMBL612545
Kd 9.84 9.84 0.1 1
Unchecked
CHEMBL612545
Ki 9.8 7.2156 0.2 9
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
Ki 9.64 9.17 0.2 6
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
EC50 9.38 6.5 0.4 3
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL4980
Ki 9.05 6.295 0.9 12
Neuronal acetylcholine receptor; alpha2/beta2
CHEMBL1907592
Ki 8.97 8.91 1.1 2
Neuronal acetylcholine receptor; alpha4/beta4
CHEMBL1907595
Ki 8.68 8.67 2.1 2
Neuronal acetylcholine receptor
CHEMBL2094110
Ki 8.6 8.6 2.5 1
Neuronal acetylcholine receptor; alpha2/beta4
CHEMBL1907590
Ki 8.27 8.27 5.4 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
EC50 8.06 8.06 8.8 1
Acetylcholine receptor; alpha1/beta1/delta/gamma
CHEMBL1907588
EC50 7.96 7.96 11.0 1
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907593
EC50 7.6 7.6 25.0 1
Neuronal acetylcholine receptor; alpha3/beta2
CHEMBL1907587
Ki 7.43 7.43 37.0 2
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907589
IC50 7.3 5.925 50.0 2
Rattus norvegicus
CHEMBL376
EC50 7.22 7.22 60.0 1
Neuronal acetylcholine receptor; alpha4/beta2
CHEMBL1907596
IC50 7.16 7.16 69.2 1
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907594
Ki 6.99 6.2738 103.0 8
Unchecked
CHEMBL612545
IC50 6.85 6.71 140.0 2
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907593
Ki 6.69 6.6767 203.0 3
Acetylcholine receptor; alpha1/beta1/delta/gamma
CHEMBL1907588
Ki 6.6 6.6 250.0 1
Acetylcholine receptor
CHEMBL2096975
Ki 6.6 6.6 250.0 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
Ki 6.16 5.655 691.0 4
Unchecked
CHEMBL612545
EC50 6.05 5.0425 900.0 4
Nicotinic acetylcholine receptor alpha 5 subunit
CHEMBL2366408
Ki 5.91 5.91 1230.0 1
Acetylcholine receptor subunit alpha
CHEMBL3097
IC50 5.45 5.45 3530.0 1
Neuronal acetylcholine receptor
CHEMBL2094110
EC50 5.0 5.0 10000.0 1
Neuronal acetylcholine receptor; alpha3/beta4
CHEMBL1907594
EC50 4.58 4.58 26000.0 1
Neuronal acetylcholine receptor; alpha3/beta2
CHEMBL2109234
EC50 4.17 4.17 67000.0 1
Neuronal acetylcholine receptor subunit alpha-7
CHEMBL2492
EC50 4.15 4.15 71000.0 2
Acetylcholine receptor subunit delta
CHEMBL3916
EC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.122 nM 9.91 Displacement of [3H]-epibatidine from rat forebrain alpha4beta2 nAChR 24156938
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.122 nM 9.91 Displacement of [3H]epibatidine from Sprague-Dawley rat brain alpha4beta2 nAChR ... 24145137
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.123 nM 9.91 In vitro binding affinity towards (alpha-4)2(beta-2)3 neuronal nicotinic acetylc... 12747776
Unchecked Kd = 0.145 nM 9.84 Binding affinity to Sprague-Dawley rat brain nAChR incubated for 75 min by scatc... 33120080
Unchecked Ki = 0.16 nM 9.8 Displacement of [3H]Cytisine from Sprague-Dawley rat brain nAChR 33120080
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.17 nM 9.77 Inhibition of [3H]nicotine binding to nicotinic acetylcholine receptor alpha4-be... 15887955
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.17 nM 9.77 Inhibition of [3H]-nicotine binding to nicotinic acetylcholine receptor alpha4-b... 15908213
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.23 nM 9.64 Binding affinity for human Nicotinic acetylcholine receptor alpha4-beta2 express... 16171993
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.23 nM 9.64 Binding affinity against nicotinic acetylcholine receptor alpha4-beta2 in human ... 15908213
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.28 nM 9.55 Displacement of [3H]cytisine from human alpha4beta2 nAChR by Cheng-Prusoff equat... 33120080
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.34 nM 9.47 Displacement of [3H]cytisine from alpha4beta2 nicotinic acetylcholine receptor i... 19548687
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.4 nM 9.4 Displacement of [3H]nicotine from rat alpha4beta2 nAChR by liquid scintillation ... 33120080
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.4 nM 9.4 Displacement of (+/-)-[3H]epibatidine from alpha4beta2 nAChR in rat cortical mem... 20478710
Neuronal acetylcholine receptor; alpha4/beta2 EC50 = 0.42 nM 9.38 Change in membrane potential in K-177 cells expressing acetylcholine central neu... 15686946
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.43 nM 9.37 Displacement of [3H]nicotine from alpha4beta2 nAChR in Sprague-Dawley rat brain ... 18356044
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 0.48 nM 9.32 Displacement of (+/-)-[3H]epibatidine from alpha4beta2 nicotinic acetylcholine r... 19548687
Neuronal acetylcholine receptor subunit alpha-7 Ki = 0.9 nM 9.05 In vitro binding affinity towards Nicotinic acetylcholine receptor alpha7 using ... 11741488
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 1.0 nM 9.0 Binding affinity to rat alpha4beta2 nAChR 23025891
Neuronal acetylcholine receptor; alpha4/beta2 Ki = 1.06 nM 8.97 Displacement of [3H]cytisine from rat alpha4beta2 nAChR in rat brain cell membra... 20880707
Neuronal acetylcholine receptor; alpha2/beta2 Ki = 1.07 nM 8.97 Displacement of [3H]epibatidine from rat alpha-2-beta-2 nACHR expressed in human... 16640326

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5724801 HEK-293T 320
- 10.6019/CHEMBL5724801 U2OS 320
- 10.6019/CHEMBL5724801 Fibroblast 320
- 10.6019/CHEMBL5303304 HEK-293T 7
- 10.6019/CHEMBL5303304 Fibroblast 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
- 10.6019/CHEMBL5303304 U2OS 5
24901260 10.1021/jm401937a Neuronal acetylcholine receptor; alpha4/beta2 5
15050613 10.1016/j.bmcl.2003.09.105 Unchecked 5
16033252 10.1021/jm040219e Unchecked 4
33120080 10.1016/j.bmc.2020.115820 Unchecked 4
15908213 10.1016/j.bmcl.2005.04.036 Neuronal acetylcholine receptor; alpha4/beta2 4
15686946 10.1016/j.bmcl.2004.11.073 Neuronal acetylcholine receptor; alpha4/beta2 3
15686946 10.1016/j.bmcl.2004.11.073 Neuronal acetylcholine receptor; alpha3/beta4 3
10377231 10.1021/jm9910223 Rattus norvegicus 3
15887955 10.1021/jm050069n Neuronal acetylcholine receptor; alpha4/beta2 3
16171993 10.1016/j.bmcl.2005.08.035 Neuronal acetylcholine receptor; alpha4/beta2 3
16033252 10.1021/jm040219e Neuronal acetylcholine receptor; alpha3/beta4 3
16033252 10.1021/jm040219e Neuronal acetylcholine receptor; alpha4/beta4 3
16033252 10.1021/jm040219e Neuronal acetylcholine receptor; alpha4/beta2 3

Data from ChEMBL 36 via Core Engine