Opipramol
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Also known as NSC-169867Opipramol duraSID90341209SID26755651SID29216400
Summary
Opipramol (CHEMBL370753) is a phase-3 clinical-stage small molecule (ATC N06AA05) targeting SIGMAR1; indicated across 6 conditions including anxiety and dementia.
At a glance
- Status: Max clinical phase 3 (not approved)
- Modality: Small molecule
- ATC class: N06AA05
- Targets: 1 (SIGMAR1)
- Indications: 6 conditions
- Clinical trials: 3
- Chemistry: 363.5 Da · C23H29N3O
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL370753 |
| Name | Opipramol |
| Type | Small molecule |
| Max phase | 3 |
| FDA approved | no |
| PubChem CID | 9417 |
| ATC | N06AA05 |
| Molecular formula | C23H29N3O |
| Molecular weight | 363.5 |
| InChIKey | YNZFUWZUGRBMHL-UHFFFAOYSA-N |
SMILES: C1CN(CCN1CCCN2C3=CC=CC=C3C=CC4=CC=CC=C42)CCO
IUPAC name: 2-[4-(3-benzo[b][1]benzazepin-11-ylpropyl)piperazin-1-yl]ethanol
Also known as: NSC-169867, Opipramol, Opipramol dura, SID90341209, SID26755651, SID29216400, OPIPRAMOL, opipramol
Parent form; salt/anhydrous children: CHEMBL1524185
Patent coverage: 1,278 distinct patent families (4,875 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 4,863 (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 |
|---|---|---|---|---|---|
| SIGMAR1 | sigma non-opioid intracellular receptor 1 | Agonist | 9.7 | 2.6% | Q99720 |
Broader ChEMBL bioactivity targets: 23 (assay-derived). Sample: Alpha-2A adrenergic receptor, Alpha-2C adrenergic receptor, Alpha-2B adrenergic receptor, D(1A) dopamine receptor, Muscarinic acetylcholine receptor M2, 5-hydroxytryptamine receptor 1A, Muscarinic acetylcholine receptor M1, D(2) dopamine receptor, Prostaglandin G/H synthase 1, Sodium-dependent noradrenaline transporter.
Bioactivity
ChEMBL activities: 17 potent at pChembl ≥ 5 of 28 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| SIGMAR1 | 9.7 | Ki | 0.2 | nM | CHEMBL_ACT_1483838 |
| EBP | 7.89 | Ki | 13 | nM | CHEMBL_ACT_1483837 |
| P32352 | 7.77 | Ki | 17 | nM | CHEMBL_ACT_1483839 |
| HRH1 | 7.09 | AC50 | 81 | nM | CHEMBL_ACT_25212205 |
| DRD3 | 6.38 | AC50 | 420 | nM | CHEMBL_ACT_25194404 |
| DRD2 | 6.05 | AC50 | 884.6 | nM | CHEMBL_ACT_25140029 |
| ADRA1A | 5.97 | AC50 | 1070 | nM | CHEMBL_ACT_25218747 |
| DRD1 | 5.89 | AC50 | 1290 | nM | CHEMBL_ACT_25115089 |
| DRD3 | 5.88 | AC50 | 1323 | nM | CHEMBL_ACT_25193231 |
| ADRA1A | 5.85 | AC50 | 1412 | nM | CHEMBL_ACT_25138368 |
| DRD1 | 5.65 | AC50 | 2239 | nM | CHEMBL_ACT_25114656 |
| SLC6A2 | 5.18 | AC50 | 6620 | nM | CHEMBL_ACT_25145879 |
| ADRA2C | 5.17 | AC50 | 6700 | nM | CHEMBL_ACT_25147572 |
| HTR1A | 5.03 | AC50 | 9250 | nM | CHEMBL_ACT_25164903 |
| ADRA2A | 5.02 | AC50 | 9600 | nM | CHEMBL_ACT_25156308 |
| CHRM2 | 5.02 | AC50 | 9580 | nM | CHEMBL_ACT_25195615 |
| ADRA2B | 5 | AC50 | 10000 | nM | CHEMBL_ACT_25143406 |
Target pathways
Aggregated over 1 target gene(s): SIGMAR1.
Top Reactome pathways
5 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Disease | 1 | SIGMAR1 |
| Infectious disease | 1 | SIGMAR1 |
| Potential therapeutics for SARS | 1 | SIGMAR1 |
| SARS-CoV Infections | 1 | SIGMAR1 |
| Viral Infection Pathways | 1 | SIGMAR1 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| lipid transport | 1 |
| nervous system development | 1 |
| regulation of neuron apoptotic process | 1 |
| protein homotrimerization | 1 |
| response to alcohol | 1 |
| regulation of postsynapse assembly | 1 |
| G protein-coupled opioid receptor signaling pathway | 1 |
Indications & clinical
Indications
6 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 |
|---|---|---|---|
| anxiety | 3 | MONDO:0011918 | EFO:0005230 |
| dementia | 3 | MONDO:0001627 | HP:0000726 |
| depressive disorder | 3 | MONDO:0002050 | MONDO:0002050 |
| drug dependence | 0 | MONDO:0005303 | EFO:0003890 |
2 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 3.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE3 | 1 |
| EARLY_PHASE1 | 1 |
| Not specified | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT02374567 | PHASE3 | TERMINATED | Pharmacovigilance in Gerontopsychiatric Patients |
| NCT03065998 | EARLY_PHASE1 | UNKNOWN | Double Blind Placebo Control Opipramol-Baclofen Treatment for Addiction |
| NCT03083405 | Not specified | ENROLLING_BY_INVITATION | Selected Disorders and Sleep Bruxism |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline, but PharmGKB curates 1 clinical and 5 variant annotation(s) for this drug (gene-keyed; see PharmGKB).
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.
143 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| METHAMPHETAMINE | ChEMBL + PubChem | Phase 4 (approved) | SIGMAR1 |
| AMANTADINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| AMIODARONE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| AMITRIPTYLINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| ASTEMIZOLE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| AZELASTINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| BENZTROPINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| BETAXOLOL | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| BREXPIPRAZOLE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| BROMHEXINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| BUFLOMEDIL | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| BUSPIRONE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| BUTENAFINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| CARBETAPENTANE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| CHLOROQUINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| CHLORPROMAZINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| CINACALCET | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| CINNARIZINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| CISAPRIDE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| CITALOPRAM | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| CLEMASTINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| CLOMIPRAMINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| CLOZAPINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| COCAINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| DEXCHLORPHENIRAMINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| DEXFENFLURAMINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| DEXTROMETHORPHAN | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| DICYCLOMINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| DIHYDROERGOTAMINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| DIMENHYDRINATE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| DIPHENIDOL | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| DOBUTAMINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| DONEPEZIL | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| DOXEPIN | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| ECONAZOLE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| FENTANYL | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| FLUOXETINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| FLUPHENAZINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| FLUVOXAMINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| HALOPERIDOL | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| HYDROXYCHLOROQUINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| ILOPERIDONE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| KETANSERIN | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| LABETALOL | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| LASMIDITAN | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| LEVAMFETAMINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| LEVOBUNOLOL | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| LOPERAMIDE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| MAZINDOL | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| MEPAZINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| METHYSERGIDE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| MIFEPRISTONE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| NAFTIFINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| OXYBUTYNIN | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| PAROXETINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| PENTAZOCINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| PERHEXILINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| PHENTOLAMINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| PIPAMAZINE | ChEMBL | Phase 4 (approved) | SIGMAR1 |
| PITOLISANT | ChEMBL | Phase 4 (approved) | SIGMAR1 |
Related Atlas pages
- Genes: SIGMAR1
- Diseases: anxiety, dementia, depressive disorder
- Drugs: Methamphetamine, Amantadine, Amiodarone, Amitriptyline, Astemizole, Azelastine, Benztropine, Betaxolol, Brexpiprazole, Bromhexine, Buflomedil, Buspirone, Butenafine, Carbetapentane, Chloroquine, Chlorpromazine, Cinacalcet, Cinnarizine, Cisapride, Citalopram, Clemastine, Clomipramine, Clozapine, Cocaine, Dexchlorpheniramine, Dexfenfluramine, Dextromethorphan, Dicyclomine, Dihydroergotamine, Dimenhydrinate, Diphenidol, Dobutamine, Donepezil, Doxepin, Econazole, Fentanyl, Fluoxetine, Fluphenazine, Fluvoxamine, Haloperidol, Hydroxychloroquine, Iloperidone, Ketanserin, Labetalol, Lasmiditan, Levamfetamine, Levobunolol, Loperamide, Mazindol, Mepazine, Methysergide, Mifepristone, Naftifine, Oxybutynin, Paroxetine, Pentazocine, Perhexiline, Phentolamine, Pipamazine, Pitolisant