Xylometazoline

Summary

Xylometazoline (CHEMBL312448) is an approved small molecule (ATC S01GA53) targeting ADRA1D, ADRA2A, and ADRA2B; indicated across 3 conditions including eye allergy and common cold.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: S01GA53 (+3 more)
• Targets: 4 (ADRA1D, ADRA2A, ADRA2B…)
• Indications: 3 conditions
• Clinical trials: 10
• Chemistry: 244.37 Da · C16H24N2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL312448
Name	Xylometazoline
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	5709
ATC	S01GA53, R01AA07, R01AB06, S01GA03
Molecular formula	C16H24N2
Molecular weight	244.37
InChIKey	HUCJFAOMUPXHDK-UHFFFAOYSA-N

SMILES: CC1=CC(=CC(=C1CC2=NCCN2)C)C(C)(C)C

IUPAC name: 2-[(4-tert-butyl-2,6-dimethylphenyl)methyl]-4,5-dihydro-1H-imidazole

Also known as: Balminil, Xilometazolina, Xylometazoline, SID11111974, SID11111975, SID90340774, SID50100368, SID50104259, SID174007471, XYLOMETAZOLINE, XYLOMETAZOLINE HYDROCHLORIDE, xylometazoline

Parent form; salt/anhydrous children: CHEMBL1256400

Patent coverage: 1,954 distinct patent families (7,459 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 7,458 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
	TAAR4P	Full agonist
ADRA1D	α1D-adrenoceptor	Agonist	6	0.2%	P25100
ADRA2A	α2A-adrenoceptor	Partial agonist	7.6	0.1%	P08913
ADRA2B	α2B-adrenoceptor	Agonist	5.4	0.2%	P18089
ADRA2C	α2C-adrenoceptor	Agonist	7	0%	P18825

Broader ChEMBL bioactivity targets: 28 (assay-derived). Sample: Prelamin-A/C, 5-hydroxytryptamine receptor 2B, Alpha-2A adrenergic receptor, 5-hydroxytryptamine receptor 1B, Adrenergic receptor alpha-1, Alpha-2C adrenergic receptor, Alpha-2B adrenergic receptor, Thyrotropin receptor, 5-hydroxytryptamine receptor 1D, Adrenergic receptor alpha-2.

Bioactivity

ChEMBL activities: 37 potent at pChembl ≥ 5 of 46 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
ADRA1A	9.52	AC50	0.3	nM	CHEMBL_ACT_25208616
HTR1D	9.15	Ki	0.7	nM	CHEMBL_ACT_1449520
HTR1D	9.15	Ki	0.7	nM	CHEMBL_ACT_454929
ADRA1A	8.64	AC50	2.3	nM	CHEMBL_ACT_25229779
P15823	8.32	Ki	4.8	nM	CHEMBL_ACT_14624392
ADRA2A	8.3	AC50	5	nM	CHEMBL_ACT_25157076
HTR1B	7.89	Ki	13	nM	CHEMBL_ACT_1449519
HTR1B	7.85	Ki	14	nM	CHEMBL_ACT_454928
HTR1A	7.75	AC50	17.8	nM	CHEMBL_ACT_25216978
P19328	7.64	IC50	23	nM	CHEMBL_ACT_164196
ADRA2A	7.52	AC50	30	nM	CHEMBL_ACT_25155930
ADRA2A	7.21	AC50	61.6	nM	CHEMBL_ACT_25219853
ADRA1A	7.04	Ki	91	nM	CHEMBL_ACT_1449522
ADRA2A	7.04	Ki	91	nM	CHEMBL_ACT_454931
ADRA2B	6.68	AC50	207.8	nM	CHEMBL_ACT_25143659
HTR2A	6.68	AC50	210	nM	CHEMBL_ACT_25225134
HTR2A	6.64	AC50	231.4	nM	CHEMBL_ACT_25226298
ADRA2C	6.62	AC50	239.4	nM	CHEMBL_ACT_25147835
HTR1D	6.43	EC50	369	nM	CHEMBL_ACT_454937
P15823	6.24	IC50	580	nM	CHEMBL_ACT_164195
HTR2B	5.93	AC50	1164	nM	CHEMBL_ACT_25228675
ADRA1A	5.9	AC50	1271	nM	CHEMBL_ACT_25137904
HTR2B	5.81	AC50	1559	nM	CHEMBL_ACT_25164098
TP53	5.5	Potency	3162	nM	CHEMBL_ACT_4838377
HTR2A	5.46	AC50	3500	nM	CHEMBL_ACT_25173600
DRD3	5.41	AC50	3873	nM	CHEMBL_ACT_25193484
TSHR	5.4	Potency	3981	nM	CHEMBL_ACT_3937309
TSHR	5.4	Potency	3981	nM	CHEMBL_ACT_4703381
CYP2D6	5.4	Potency	3981	nM	CHEMBL_ACT_4998405
CYP2D6	5.4	AC50	3981	nM	CHEMBL_ACT_5988745

Target pathways

Aggregated over 4 target gene(s): ADRA1D, ADRA2A, ADRA2B, ADRA2C.

Top Reactome pathways

21 total, by targets touching each:

Pathway	Targets	Genes
Signal Transduction	4	ADRA1D, ADRA2A, ADRA2B, ADRA2C
Signaling by GPCR	4	ADRA1D, ADRA2A, ADRA2B, ADRA2C
Class A/1 (Rhodopsin-like receptors)	4	ADRA1D, ADRA2A, ADRA2B, ADRA2C
Amine ligand-binding receptors	4	ADRA1D, ADRA2A, ADRA2B, ADRA2C
GPCR downstream signalling	4	ADRA1D, ADRA2A, ADRA2B, ADRA2C
Adrenoceptors	4	ADRA1D, ADRA2A, ADRA2B, ADRA2C
GPCR ligand binding	4	ADRA1D, ADRA2A, ADRA2B, ADRA2C
Hemostasis	3	ADRA2A, ADRA2B, ADRA2C
Adrenaline signalling through Alpha-2 adrenergic receptor	3	ADRA2A, ADRA2B, ADRA2C
G alpha (i) signalling events	3	ADRA2A, ADRA2B, ADRA2C
G alpha (z) signalling events	3	ADRA2A, ADRA2B, ADRA2C
Platelet activation, signaling and aggregation	3	ADRA2A, ADRA2B, ADRA2C
Platelet Aggregation (Plug Formation)	3	ADRA2A, ADRA2B, ADRA2C
Metabolism	2	ADRA2A, ADRA2C
Integration of energy metabolism	2	ADRA2A, ADRA2C
Metabolism of proteins	2	ADRA2A, ADRA2C
Adrenaline,noradrenaline inhibits insulin secretion	2	ADRA2A, ADRA2C
Regulation of insulin secretion	2	ADRA2A, ADRA2C
Surfactant metabolism	2	ADRA2A, ADRA2C
G alpha (q) signalling events	1	ADRA1D
G alpha (12/13) signalling events	1	ADRA1D

Dominant GO biological processes

GO term	Targets
G protein-coupled receptor signaling pathway	4
positive regulation of MAPK cascade	4
signal transduction	4
adrenergic receptor signaling pathway	4
cell-cell signaling	3
epidermal growth factor receptor signaling pathway	3
negative regulation of norepinephrine secretion	3
regulation of vasoconstriction	3
platelet activation	3
negative regulation of epinephrine secretion	3
positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transduction	3
adenylate cyclase-inhibiting adrenergic receptor signaling pathway	3
regulation of smooth muscle contraction	3
positive regulation of cell population proliferation	2
adenylate cyclase-activating adrenergic receptor signaling pathway	2

Indications & clinical

Indications

3 indications (2 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
eye allergy	4	MONDO:0005551	EFO:0005751
common cold	3	MONDO:0005709	EFO:0007214

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

Clinical trials

Total trials: 10.

Phase distribution

Phase	Trials
Not specified	6
PHASE4	2
PHASE3	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT00630474	PHASE4	COMPLETED	Nasal Decongestion and Obstructive Sleep Apnea
NCT05334017	PHASE4	COMPLETED	Xylometazoline and Cocaine for Nasal Vasoconstriction
NCT00452270	PHASE3	COMPLETED	Decongestant Effect, Timing of Effect and Impact on Sleep and General Well-Being of Xylometazoline in Subjects With a Common Cold
NCT06443255	PHASE3	COMPLETED	Cocaine, Lidocaine/xylometazoline and Saline for Nasal Analgesia
NCT00480194	Not specified	COMPLETED	Evaluation of Safety of ZyComb® In Patients With Common Cold - ZIP 3000 (XY-005-IM)
NCT00622817	Not specified	COMPLETED	The Influence of Inhaled Adrenalin Versus Decongestant as a Local Nasal Treatment in Bronchiolitis
NCT03072173	Not specified	UNKNOWN	The Role of the Nose in Snoring and Sleep Apnea
NCT03424889	Not specified	COMPLETED	Xylometazoline During Nasal Flexible Bronchoscopy
NCT05804123	Not specified	COMPLETED	LiveSpo Navax® Supports the Treatment of Acute Rhinosinusitis and Otitis Media
NCT05999955	Not specified	COMPLETED	Safety and Efficacy of DSM 32444 Postbiotic in the Treatment of Acute Rhinosinusitis

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

616 molecules share ≥1 primary target. Top 60 by shared-target count:

Molecule	Source	Status	Shared targets
CLOZAPINE	ChEMBL + PubChem	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
DIHYDROERGOTAMINE	ChEMBL + PubChem	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
GENTIAN VIOLET	ChEMBL + PubChem	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
OLANZAPINE	ChEMBL + PubChem	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
Pramipexole	ChEMBL + PubChem	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
TAMSULOSIN	ChEMBL + PubChem	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
TEGASEROD	ChEMBL + PubChem	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
ALFUZOSIN	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
AMITRIPTYLINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
AMOXAPINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
APOMORPHINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
APRACLONIDINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
ARIPIPRAZOLE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
ASENAPINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
ASTEMIZOLE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
AZELASTINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
BENZTROPINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
BREXPIPRAZOLE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
BRIMONIDINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
BROMOCRIPTINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
CARIPRAZINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
CARVEDILOL	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
CHLORPROMAZINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
CINNARIZINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
CISAPRIDE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
CLEMASTINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
CLOMIPRAMINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
CLONIDINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
CLOTRIMAZOLE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
CYPROHEPTADINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
DEXMEDETOMIDINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
DIETHYLSTILBESTROL	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
DOBUTAMINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
DOMPERIDONE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
DOXAZOSIN	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
DOXEPIN	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
DROPERIDOL	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
EBASTINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
ECONAZOLE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
EPINEPHRINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
ERGOTAMINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
FLUPHENAZINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
GUANABENZ	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
GUANFACINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
HALOPERIDOL	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
HYDROXYCHLOROQUINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
INDORAMIN	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
KETOTIFEN	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
LABETALOL	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
MAPROTILINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
MIANSERIN	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
MOXISYLYTE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
NAFTOPIDIL	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
NEFAZODONE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
NOREPINEPHRINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
NORTRIPTYLINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
OXYMETAZOLINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
PERGOLIDE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
PHENTOLAMINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C
PIPAMAZINE	ChEMBL	Phase 4 (approved)	ADRA1D, ADRA2A, ADRA2B, ADRA2C