Cytisinicline

Summary

Cytisinicline (CHEMBL497939) is an approved small-molecule nicotinic acetylcholine receptor agonist (ATC N07BA04); indicated across 3 conditions including nicotine dependence and kidney disorder.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: N07BA04
• Indications: 3 conditions
• Clinical trials: 30
• Chemistry: 190.24 Da · C11H14N2O

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL497939
Name	Cytisinicline
Type	Small molecule
Max phase	3
FDA approved	yes
PubChem CID	10235
ChEBI	CHEBI:4055
ATC	N07BA04
Molecular formula	C11H14N2O
Molecular weight	190.24
InChIKey	ANJTVLIZGCUXLD-DTWKUNHWSA-N

SMILES: C1[C@H]2CNC[C@@H]1C3=CC=CC(=O)N3C2

IUPAC name: (1R,9S)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one

ChEBI definition: An organic heterotricyclic compound that is the toxic principle in Laburnum seeds and is found in many members of the Fabaceae (legume, pea or bean) family. An acetylcholine agonist, it is widely used throughout Eastern Europe as an aid to giving up smoking.

Pharmacological roles (ChEBI): nicotinic acetylcholine receptor agonist, phytotoxin.

Other ChEBI roles (chemical / environmental): plant metabolite.

Also known as: 6039 Sopharma, Baptitoxine, Citisiniclina, Cytisine, Cytisinicline, Cytiton, NSC-407282, Sophorine, Tabex, Ulexine, (-)-cytisine, cytisine

Patent coverage: 1,240 distinct patent families (2,766 SureChEMBL compound mentions), from 1 matched compound structure(s). Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 23 (assay-derived). Sample: Microtubule-associated protein tau, Lysine-specific demethylase 4E, Prelamin-A/C, Inositol monophosphatase 1, Neuronal acetylcholine receptor; alpha3/beta2, Acetylcholine receptor; alpha1/beta1/delta/gamma, Neuronal acetylcholine receptor; alpha4/beta2, Neuronal acetylcholine receptor; alpha2/beta4, Neuronal acetylcholine receptor; alpha2/beta2, Neuronal acetylcholine receptor; alpha3/beta4.

Bioactivity

ChEMBL activities: 79 potent at pChembl ≥ 5 of 94 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
P09483	9.91	Ki	0.12	nM	CHEMBL_ACT_1125240
P09483	9.91	Ki	0.12	nM	CHEMBL_ACT_13853871
P09483	9.91	Ki	0.12	nM	CHEMBL_ACT_13858648
P09483	9.77	Ki	0.17	nM	CHEMBL_ACT_1482202
P09483	9.77	Ki	0.17	nM	CHEMBL_ACT_1513639
CHRNB2	9.7	Ki	0.2	nM	CHEMBL_ACT_29199813
CHRNB2	9.7	Ki	0.2	nM	CHEMBL_ACT_29199822
CHRNB2	9.68	Kd	0.21	nM	CHEMBL_ACT_29199857
CHRNB2	9.64	Ki	0.23	nM	CHEMBL_ACT_1482201
CHRNB2	9.64	Ki	0.23	nM	CHEMBL_ACT_1615704
CHRNB2	9.55	Ki	0.28	nM	CHEMBL_ACT_22432896
P09483	9.47	Ki	0.34	nM	CHEMBL_ACT_2296446
P09483	9.4	Ki	0.4	nM	CHEMBL_ACT_22432906
P09483	9.4	Ki	0.4	nM	CHEMBL_ACT_3330618
CHRNB2	9.38	EC50	0.42	nM	CHEMBL_ACT_1421289
P09483	9.37	Ki	0.43	nM	CHEMBL_ACT_2122671
P09483	9.32	Ki	0.48	nM	CHEMBL_ACT_2296390
Q05941	9.05	Ki	0.9	nM	CHEMBL_ACT_811395
P09483	9	Ki	1	nM	CHEMBL_ACT_12156121
P12389	8.97	Ki	1.07	nM	CHEMBL_ACT_1711746
P09483	8.97	Ki	1.06	nM	CHEMBL_ACT_3530597
CHRNB2	8.9	Ki	1.27	nM	CHEMBL_ACT_29015918
P12389	8.85	Ki	1.4	nM	CHEMBL_ACT_284556
P09483	8.82	Ki	1.51	nM	CHEMBL_ACT_1711782
P09483	8.82	Ki	1.5	nM	CHEMBL_ACT_284560
P09483	8.81	Ki	1.53	nM	CHEMBL_ACT_3561636
P09483	8.72	Ki	1.92	nM	CHEMBL_ACT_1711800
CHRNB2	8.7	Ki	2	nM	CHEMBL_ACT_15023463
P09483	8.68	Ki	2.1	nM	CHEMBL_ACT_12700357
P09483	8.68	Ki	2.1	nM	CHEMBL_ACT_1711791

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

3 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
nicotine dependence	3	MONDO:0008575	EFO:0003768
kidney disorder	1	MONDO:0005240	EFO:0003086

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 30.

Phase distribution

Phase	Trials
PHASE3	8
PHASE1	7
Not specified	5
PHASE4	4
PHASE2	4
PHASE2/PHASE3	1
PHASE1/PHASE2	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT06579846	PHASE4	NOT_YET_RECRUITING	12-Month Efficacy of Exercise and Cytisinicline for Tobacco Abstinence
NCT06832085	PHASE4	RECRUITING	Combination Nicotine Replacement Therapy, Cytisine, or Varenicline for Smoking Cessation
NCT04126135	PHASE4	COMPLETED	Comparative Effectiveness of Cystine Versus Nicotine Replacement Therapy
NCT05729243	PHASE4	COMPLETED	Cytisine for Smoking Cessation
NCT05102123	PHASE3	ACTIVE_NOT_RECRUITING	PeRiopEratiVE SmokiNg CessaTion Trial
NCT07392125	PHASE3	NOT_YET_RECRUITING	Phase 3 Trial Evaluating the Efficacy and Safety of Cytisinicline for Vaping Cessation in Adults Using Nicotine-Containing E Cigarettes
NCT02797587	PHASE2/PHASE3	COMPLETED	Studying Partial-agonists for Ethanol and Tobacco Elimination in Russians With HIV (St PETER HIV)
NCT02957786	PHASE3	COMPLETED	Cytisine Versus Varenicline for Smoking Cessation
NCT04015414	PHASE3	COMPLETED	Varenicline Versus Cytisine for Smoking Cessation in Primary Care Setting
NCT04576949	PHASE3	COMPLETED	A Study of Cytisinicline for Smoking Cessation in Adult Smokers
NCT05206370	PHASE3	COMPLETED	A Second Study of Cytisinicline for Smoking Cessation in Adult Smokers
NCT05311085	PHASE3	COMPLETED	Cytisine and E-cigarettes With Supportive Text-messaging for Smoking Cessation (Cess@Tion)
NCT06435221	PHASE3	COMPLETED	Safety Study of Cytisinicline in Adult Combustible and/or E-cigarette Smokers
NCT03654105	PHASE2	ACTIVE_NOT_RECRUITING	Screening and Multiple Intervention on Lung Epidemics
NCT06617312	PHASE2	RECRUITING	Examining the Effects of Cytisinicline on Neural Substrates of Cigarette Cue-reactivity
NCT03303911	PHASE1/PHASE2	TERMINATED	A Pharmacokinetic and Pharmacodynamic Evaluation of Cytisine in Healthy Smokers
NCT03709823	PHASE2	COMPLETED	Trial of Cytisine in Adult Smokers
NCT05431387	PHASE2	COMPLETED	A Study of Cytisinicline for Vaping Cessation in Adult Smokers
NCT02585024	PHASE1	TERMINATED	Cytisine Pharmacokinetics and Dose Response (C-DRAKS 3 and C-DRAKS 4)
NCT03268343	PHASE1	COMPLETED	A Study in Healthy Volunteers to Investigate the Effect of Food on the Bioavailability of Cytisine
NCT03509948	PHASE1	COMPLETED	A Study in Healthy Smokers to Investigate the Effect of Food on the Bioavailability of Cytisine in a New Formulation
NCT03848208	PHASE1	COMPLETED	A Single Dose-escalation Study of Cytisine in Adult Smokers
NCT05566288	PHASE1	COMPLETED	Study to Evaluate Electrocardiographic Effects of Therapeutic & Supratherapeutic Doses of Cytisinicline in Healthy Smokers
NCT05631938	PHASE1	COMPLETED	Study to Evaluate the Effect of Renal Impairment and Dialysis Treatment on the Pharmacokinetics of a Single 3 mg Cytisinicline Dose
NCT05981768	PHASE1	COMPLETED	Study to Evaluate Effect of Food on Bioavailability of Single 3 mg Tablet and Pharmacokinetics (PK) of Multiple 3 mg Doses in Healthy Adult Smokers
NCT03249428	Not specified	ENROLLING_BY_INVITATION	Cytisine vs Nicotine Replacement Therapy
NCT06439303	Not specified	RECRUITING	Analysis and Evaluation of Smoking Treatment With Cytisine
NCT06885970	Not specified	RECRUITING	The Effect of Cytisine Treatment for Smoking Cessation on Cardiovascular Function in Adult Smokers
NCT07274475	Not specified	NOT_YET_RECRUITING	Smoking Harm Reduction Using E-cigarettes and Cytisine
NCT04286295	Not specified	TERMINATED	Cytisine Compared to Combination NRT in Relapsed Smokers

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).