Tolazoline
drugOn this page
Also known as NSC-35110TolazineTolazolinaSID11112156TOLAZOLINE HYDROCHLORIDE
Summary
Tolazoline (CHEMBL770) is an approved small-molecule α-adrenergic antagonist (ATC M02AX02) targeting ADRA2A, ADRA2B, and ADRA2C; indicated across 3 conditions including cardiovascular disorder.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: M02AX02 (+1 more)
- Targets: 3 (ADRA2A, ADRA2B, ADRA2C)
- Indications: 3 conditions
- Chemistry: 160.22 Da · C10H12N2
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL770 |
| Name | Tolazoline |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 5504 |
| ChEBI | CHEBI:28502 |
| ATC | M02AX02, C04AB02 |
| Molecular formula | C10H12N2 |
| Molecular weight | 160.22 |
| InChIKey | JIVZKJJQOZQXQB-UHFFFAOYSA-N |
SMILES: C1CN=C(N1)CC2=CC=CC=C2
IUPAC name: 2-benzyl-4,5-dihydro-1H-imidazole
ChEBI definition: A member of the class of imidazoles that is 4,5-dihydro-1H-imidazole substituted by a benzyl group.
Pharmacological roles (ChEBI): α-adrenergic antagonist, antihypertensive agent, vasodilator agent.
Also known as: NSC-35110, Tolazine, Tolazolina, Tolazoline, tolazoline, SID11112156, TOLAZOLINE, TOLAZOLINE HYDROCHLORIDE
Parent form; salt/anhydrous children: CHEMBL1689
Patent coverage: 3,468 distinct patent families (10,239 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
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 |
|---|---|---|---|---|---|
| ADRA2A | α2A-adrenoceptor | Antagonist | 6.7 | 0.1% | P08913 |
| ADRA2B | α2B-adrenoceptor | Antagonist | 5.5 | 0.2% | P18089 |
| ADRA2C | α2C-adrenoceptor | Antagonist | 5.43 | 0% | P18825 |
Broader ChEMBL bioactivity targets: 12 (assay-derived). Sample: Prelamin-A/C, Alpha-2A adrenergic receptor, Adrenergic receptor alpha-1, Alpha-2C adrenergic receptor, Alpha-2B adrenergic receptor, Thyrotropin receptor, Adrenergic receptor alpha-2, Adrenergic receptor alpha-1, Alpha-1A adrenergic receptor, Cytochrome P450 2D6.
Bioactivity
ChEMBL activities: 13 potent at pChembl ≥ 5 of 17 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| LMNA | 6.75 | Potency | 177.8 | nM | CHEMBL_ACT_3639842 |
| P19328 | 6.75 | Ki | 180 | nM | CHEMBL_ACT_538351 |
| P19328 | 6.55 | IC50 | 280 | nM | CHEMBL_ACT_170363 |
| ADRA2A | 6.08 | AC50 | 840 | nM | CHEMBL_ACT_25220563 |
| P19328 | 5.82 | Kd | 1514 | nM | CHEMBL_ACT_170359 |
| TAAR1 | 5.79 | Ki | 1640 | nM | CHEMBL_ACT_12188260 |
| ADRA1A | 5.72 | AC50 | 1900 | nM | CHEMBL_ACT_25230376 |
| P15823 | 5.68 | IC50 | 2100 | nM | CHEMBL_ACT_170362 |
| P15823 | 5.66 | Kd | 2188 | nM | CHEMBL_ACT_170358 |
| ADRA1D | 5.41 | Kd | 3890 | nM | CHEMBL_ACT_170360 |
| ADRA2C | 5.3 | AC50 | 5000 | nM | CHEMBL_ACT_25148589 |
| ADRA2B | 5.11 | AC50 | 7800 | nM | CHEMBL_ACT_25144389 |
| CYP1A2 | 5 | AC50 | 10000 | nM | CHEMBL_ACT_6051135 |
Target pathways
Aggregated over 3 target gene(s): ADRA2A, ADRA2B, ADRA2C.
Top Reactome pathways
19 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Hemostasis | 3 | ADRA2A, ADRA2B, ADRA2C |
| Signal Transduction | 3 | ADRA2A, ADRA2B, ADRA2C |
| Signaling by GPCR | 3 | ADRA2A, ADRA2B, ADRA2C |
| Class A/1 (Rhodopsin-like receptors) | 3 | ADRA2A, ADRA2B, ADRA2C |
| Amine ligand-binding receptors | 3 | ADRA2A, ADRA2B, ADRA2C |
| GPCR downstream signalling | 3 | ADRA2A, ADRA2B, ADRA2C |
| Adrenoceptors | 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 |
| GPCR ligand binding | 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 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| epidermal growth factor receptor signaling pathway | 3 |
| G protein-coupled 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 MAPK cascade | 3 |
| positive regulation of phosphatidylinositol 3-kinase/protein kinase B signal transduction | 3 |
| adrenergic receptor signaling pathway | 3 |
| adenylate cyclase-inhibiting adrenergic receptor signaling pathway | 3 |
| regulation of smooth muscle contraction | 3 |
| signal transduction | 3 |
| adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway | 2 |
| female pregnancy | 2 |
| negative regulation of insulin secretion | 2 |
Indications & clinical
Indications
3 indications (3 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 |
|---|---|---|---|
| cardiovascular disorder | 4 | MONDO:0004995 | EFO:0000319 |
2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 0.
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.
607 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| ACLIDINIUM BROMIDE | ChEMBL + PubChem | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| Afatinib | ChEMBL + PubChem | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| Almotriptan | ChEMBL + PubChem | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| CHENODIOL | ChEMBL + PubChem | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| CLOZAPINE | ChEMBL + PubChem | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| CRIZOTINIB | ChEMBL + PubChem | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| DESLORATADINE | ChEMBL + PubChem | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| DIHYDROERGOTAMINE | ChEMBL + PubChem | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| GENTIAN VIOLET | ChEMBL + PubChem | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| NAPHAZOLINE | ChEMBL + PubChem | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| OLANZAPINE | ChEMBL + PubChem | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| OLODATEROL | ChEMBL + PubChem | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| PALIPERIDONE | ChEMBL + PubChem | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| PRAMIPEXOLE | ChEMBL + PubChem | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| TAMSULOSIN | ChEMBL + PubChem | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| TEGASEROD | ChEMBL + PubChem | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| ACETOPHENAZINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| ALFUZOSIN | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| AMISULPRIDE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| AMITRIPTYLINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| AMOXAPINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| APOMORPHINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| APRACLONIDINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| ARIPIPRAZOLE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| ASENAPINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| ASTEMIZOLE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| AZELASTINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| BAZEDOXIFENE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| BENFLUOREX | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| BENPERIDOL | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| BENZBROMARONE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| BENZQUINAMIDE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| BENZTHIAZIDE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| BENZTROPINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| BITHIONOL | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| BREXPIPRAZOLE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| BRIMONIDINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| BROMOCRIPTINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| BROMPERIDOL | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| CABERGOLINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| CANDESARTAN CILEXETIL | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| CARIPRAZINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| CARVEDILOL | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| CHLORHEXIDINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| CHLOROQUINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| CHLORPROMAZINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| CINNARIZINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| CISAPRIDE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| CLEMASTINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| CLOMIPRAMINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| CLONIDINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| CLOTRIMAZOLE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| CYPROHEPTADINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| DANAZOL | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| DARIFENACIN | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| DEXMEDETOMIDINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| DIETHYLSTILBESTROL | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| DOBUTAMINE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| DOMPERIDONE | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
| DOTHIEPIN | ChEMBL | Phase 4 (approved) | ADRA2A, ADRA2B, ADRA2C |
Related Atlas pages
- Genes: ADRA2A, ADRA2B, ADRA2C
- Diseases: cardiovascular disorder
- Drugs: Aclidinium Bromide, Afatinib, Almotriptan, Chenodiol, Clozapine, Crizotinib, Desloratadine, Dihydroergotamine, Naphazoline, Olanzapine, Olodaterol, Paliperidone, Pramipexole, Tamsulosin, Tegaserod, Acetophenazine, Alfuzosin, Amisulpride, Amitriptyline, Amoxapine, Apomorphine, Apraclonidine, Aripiprazole, Asenapine, Astemizole, Azelastine, Bazedoxifene, Benfluorex, Benperidol, Benzbromarone, Benzquinamide, Benzthiazide, Benztropine, Bithionol, Brexpiprazole, Brimonidine, Bromocriptine, Bromperidol, Cabergoline, Candesartan Cilexetil, Cariprazine, Carvedilol, Chlorhexidine, Chloroquine, Chlorpromazine, Cinnarizine, Cisapride, Clemastine, Clomipramine, Clonidine, Clotrimazole, Cyproheptadine, Danazol, Darifenacin, Dexmedetomidine, Diethylstilbestrol, Dobutamine, Domperidone, Dothiepin