Metaproterenol
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Also known as OrciprenalinaOrciprenalineSID26748125SID90340962C0164839
Summary
Metaproterenol (CHEMBL776) is an approved small molecule (ATC R03AB03) targeting ADRB2; indicated across 1 condition including obstructive lung disease.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: R03AB03 (+1 more)
- Targets: 1 (ADRB2)
- Indications: 1 condition
- Chemistry: 211.26 Da · C11H17NO3
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL776 |
| Name | Metaproterenol |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 4086 |
| ChEBI | CHEBI:83329 |
| ATC | R03AB03, R03CB03 |
| Molecular formula | C11H17NO3 |
| Molecular weight | 211.26 |
| InChIKey | LMOINURANNBYCM-UHFFFAOYSA-N |
SMILES: CC(C)NCC(C1=CC(=CC(=C1)O)O)O
IUPAC name: 5-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,3-diol
ChEBI definition: A member of the class of resorcinols bearing an additional 1-hydroxy-2-(isopropanylamino)ethyl substituent at position 5 of resorcinol itself.
Also known as: Orciprenalina, Orciprenaline, metaproterenol, Metaproterenol, SID26748125, SID90340962, METAPROTERENOL, C0164839, orciprenaline
Parent form; salt/anhydrous children: CHEMBL1568057, CHEMBL1628446, CHEMBL2164775
Patent coverage: 5,271 distinct patent families (22,054 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 |
|---|---|---|---|---|---|
| ADRB2 | β2-adrenoceptor | Agonist | 5.32 | 0.4% | P07550 |
Broader ChEMBL bioactivity targets: 4 (assay-derived). Sample: Nuclear receptor ROR-gamma, Beta-2 adrenergic receptor, Alpha-1A adrenergic receptor, Beta-2 adrenergic receptor.
Bioactivity
ChEMBL activities: 5 potent at pChembl ≥ 5 of 5 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| ADRB2 | 6.3 | Kd | 501.2 | nM | CHEMBL_ACT_13449576 |
| ADRA1A | 5.51 | AC50 | 3106 | nM | CHEMBL_ACT_25208382 |
| ADRB2 | 5.32 | Kd | 4810 | nM | CHEMBL_ACT_2688155 |
| P51450 | 5.25 | Potency | 5623 | nM | CHEMBL_ACT_4996322 |
| Q28044 | 5.04 | Kd | 9120 | nM | CHEMBL_ACT_477233 |
Target pathways
Aggregated over 1 target gene(s): ADRB2.
Top Reactome pathways
16 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Signal Transduction | 1 | ADRB2 |
| Membrane Trafficking | 1 | ADRB2 |
| Signaling by GPCR | 1 | ADRB2 |
| Class A/1 (Rhodopsin-like receptors) | 1 | ADRB2 |
| Amine ligand-binding receptors | 1 | ADRB2 |
| GPCR downstream signalling | 1 | ADRB2 |
| Adrenoceptors | 1 | ADRB2 |
| Metabolism of proteins | 1 | ADRB2 |
| G alpha (s) signalling events | 1 | ADRB2 |
| GPCR ligand binding | 1 | ADRB2 |
| Vesicle-mediated transport | 1 | ADRB2 |
| Deubiquitination | 1 | ADRB2 |
| Ub-specific processing proteases | 1 | ADRB2 |
| Post-translational protein modification | 1 | ADRB2 |
| Cargo recognition for clathrin-mediated endocytosis | 1 | ADRB2 |
| Clathrin-mediated endocytosis | 1 | ADRB2 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| diet induced thermogenesis | 1 |
| norepinephrine-epinephrine-mediated vasodilation involved in regulation of systemic arterial blood pressure | 1 |
| regulation of sodium ion transport | 1 |
| transcription by RNA polymerase II | 1 |
| receptor-mediated endocytosis | 1 |
| smooth muscle contraction | 1 |
| cell surface receptor signaling pathway | 1 |
| adenylate cyclase-modulating G protein-coupled receptor signaling pathway | 1 |
| endosome to lysosome transport | 1 |
| response to cold | 1 |
| positive regulation of cardiac muscle cell apoptotic process | 1 |
| negative regulation of cardiac muscle cell apoptotic process | 1 |
| positive regulation of bone mineralization | 1 |
| heat generation | 1 |
| negative regulation of multicellular organism growth | 1 |
Indications & clinical
Indications
1 indication (1 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 |
|---|---|---|---|
| obstructive lung disease | 4 | MONDO:0002267 | HP:0006536 |
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.
188 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| DESLORATADINE | ChEMBL + PubChem | Phase 4 (approved) | ADRB2 |
| DIHYDROERGOTAMINE | ChEMBL + PubChem | Phase 4 (approved) | ADRB2 |
| OLODATEROL | ChEMBL + PubChem | Phase 4 (approved) | ADRB2 |
| PRAMIPEXOLE | ChEMBL + PubChem | Phase 4 (approved) | ADRB2 |
| ACEBUTOLOL | ChEMBL | Phase 4 (approved) | ADRB2 |
| ADENOSINE | ChEMBL | Phase 4 (approved) | ADRB2 |
| ALBUTEROL | ChEMBL | Phase 4 (approved) | ADRB2 |
| AMITRIPTYLINE | ChEMBL | Phase 4 (approved) | ADRB2 |
| AMLODIPINE | ChEMBL | Phase 4 (approved) | ADRB2 |
| AMOXAPINE | ChEMBL | Phase 4 (approved) | ADRB2 |
| ARFORMOTEROL | ChEMBL | Phase 4 (approved) | ADRB2 |
| ARIPIPRAZOLE | ChEMBL | Phase 4 (approved) | ADRB2 |
| ATENOLOL | ChEMBL | Phase 4 (approved) | ADRB2 |
| BENPERIDOL | ChEMBL | Phase 4 (approved) | ADRB2 |
| BETAXOLOL | ChEMBL | Phase 4 (approved) | ADRB2 |
| BISOPROLOL | ChEMBL | Phase 4 (approved) | ADRB2 |
| BREXPIPRAZOLE | ChEMBL | Phase 4 (approved) | ADRB2 |
| BROMOCRIPTINE | ChEMBL | Phase 4 (approved) | ADRB2 |
| CANDESARTAN CILEXETIL | ChEMBL | Phase 4 (approved) | ADRB2 |
| CARTEOLOL | ChEMBL | Phase 4 (approved) | ADRB2 |
| CARVEDILOL | ChEMBL | Phase 4 (approved) | ADRB2 |
| CELIPROLOL | ChEMBL | Phase 4 (approved) | ADRB2 |
| CHLORHEXIDINE | ChEMBL | Phase 4 (approved) | ADRB2 |
| CLEMASTINE | ChEMBL | Phase 4 (approved) | ADRB2 |
| CLOMIPRAMINE | ChEMBL | Phase 4 (approved) | ADRB2 |
| CLOTRIMAZOLE | ChEMBL | Phase 4 (approved) | ADRB2 |
| CLOZAPINE | ChEMBL | Phase 4 (approved) | ADRB2 |
| DARIFENACIN | ChEMBL | Phase 4 (approved) | ADRB2 |
| DEXAMETHASONE | ChEMBL | Phase 4 (approved) | ADRB2 |
| DIPIVEFRIN | ChEMBL | Phase 4 (approved) | ADRB2 |
| DOBUTAMINE | ChEMBL | Phase 4 (approved) | ADRB2 |
| DOMPERIDONE | ChEMBL | Phase 4 (approved) | ADRB2 |
| DOPAMINE | ChEMBL | Phase 4 (approved) | ADRB2 |
| DOXAZOSIN | ChEMBL | Phase 4 (approved) | ADRB2 |
| ELAGOLIX | ChEMBL | Phase 4 (approved) | ADRB2 |
| EPINEPHRINE | ChEMBL | Phase 4 (approved) | ADRB2 |
| EPINEPHRINE BITARTRATE | ChEMBL | Phase 4 (approved) | ADRB2 |
| ERGOTAMINE | ChEMBL | Phase 4 (approved) | ADRB2 |
| ESMOLOL | ChEMBL | Phase 4 (approved) | ADRB2 |
| FENOTEROL | ChEMBL | Phase 4 (approved) | ADRB2 |
| FLUSPIRILENE | ChEMBL | Phase 4 (approved) | ADRB2 |
| FORMOTEROL | ChEMBL | Phase 4 (approved) | ADRB2 |
| HALOPERIDOL | ChEMBL | Phase 4 (approved) | ADRB2 |
| INDACATEROL | ChEMBL | Phase 4 (approved) | ADRB2 |
| ISOETHARINE | ChEMBL | Phase 4 (approved) | ADRB2 |
| ISOPROTERENOL | ChEMBL | Phase 4 (approved) | ADRB2 |
| LABETALOL | ChEMBL | Phase 4 (approved) | ADRB2 |
| LEVOBUNOLOL | ChEMBL | Phase 4 (approved) | ADRB2 |
| LEVOSALBUTAMOL | ChEMBL | Phase 4 (approved) | ADRB2 |
| LOFEPRAMINE | ChEMBL | Phase 4 (approved) | ADRB2 |
| LOPERAMIDE | ChEMBL | Phase 4 (approved) | ADRB2 |
| LOXAPINE | ChEMBL | Phase 4 (approved) | ADRB2 |
| MEBEVERINE | ChEMBL | Phase 4 (approved) | ADRB2 |
| METOPROLOL | ChEMBL | Phase 4 (approved) | ADRB2 |
| MIFEPRISTONE | ChEMBL | Phase 4 (approved) | ADRB2 |
| MONTELUKAST | ChEMBL | Phase 4 (approved) | ADRB2 |
| NADOLOL | ChEMBL | Phase 4 (approved) | ADRB2 |
| NEBIVOLOL | ChEMBL | Phase 4 (approved) | ADRB2 |
| NITAZOXANIDE | ChEMBL | Phase 4 (approved) | ADRB2 |
| NOREPINEPHRINE | ChEMBL | Phase 4 (approved) | ADRB2 |
Related Atlas pages
- Genes: ADRB2
- Diseases: obstructive lung disease
- Drugs: Desloratadine, Dihydroergotamine, Olodaterol, Pramipexole, Acebutolol, Adenosine, Albuterol, Amitriptyline, Amlodipine, Amoxapine, Arformoterol, Aripiprazole, Atenolol, Benperidol, Betaxolol, Bisoprolol, Brexpiprazole, Bromocriptine, Candesartan Cilexetil, Carteolol, Carvedilol, Celiprolol, Chlorhexidine, Clemastine, Clomipramine, Clotrimazole, Clozapine, Darifenacin, Dexamethasone, Dipivefrin, Dobutamine, Domperidone, Dopamine, Doxazosin, Elagolix, Epinephrine, Ergotamine, Esmolol, Fenoterol, Fluspirilene, Formoterol, Haloperidol, Indacaterol, Isoetharine, Isoproterenol, Labetalol, Levobunolol, Levosalbutamol, Lofepramine, Loperamide, Loxapine, Mebeverine, Metoprolol, Mifepristone, Montelukast, Nadolol, Nebivolol, Nitazoxanide, Norepinephrine