Trimipramine
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Also known as 7162 RPIL 6001IL-6001TrimeproprimineTrimipraminaSID90341093SID50111256
Summary
Trimipramine (CHEMBL644) is an approved small-molecule antidepressant (ATC N06AA06) targeting SLC6A2, SLC6A3, and SLC6A4; indicated across 5 conditions including depressive disorder and anxiety.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: N06AA06
- Targets: 3 (SLC6A2, SLC6A3, SLC6A4)
- Indications: 5 conditions
- Clinical trials: 3
- Chemistry: 294.4 Da · C20H26N2
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL644 |
| Name | Trimipramine |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 5584 |
| ChEBI | CHEBI:9738 |
| ATC | N06AA06 |
| Molecular formula | C20H26N2 |
| Molecular weight | 294.4 |
| InChIKey | ZSCDBOWYZJWBIY-UHFFFAOYSA-N |
SMILES: CC(CN1C2=CC=CC=C2CCC3=CC=CC=C31)CN(C)C
IUPAC name: 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N,2-trimethylpropan-1-amine
ChEBI definition: A dibenzoazepine that is 10,11-dihydro-5H-dibenzo[b,f]azepine substituted by a 3-(dimethylamino)-2-methylpropyl group at the nitrogen atom. It is used as an antidepressant.
Pharmacological roles (ChEBI): antidepressant.
Other ChEBI roles (chemical / environmental): environmental contaminant, xenobiotic.
Also known as: 7162 RP, IL 6001, IL-6001, Trimeproprimine, Trimipramina, Trimipramine, trimipramine, SID90341093, SID50111256, TRIMIPRAMINE
Parent form; salt/anhydrous children: CHEMBL1200948
Patent coverage: 5,114 distinct patent families (19,638 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 19,585 (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 |
|---|---|---|---|---|---|
| SLC6A2 | NET | Inhibition | 5.61 | 0.4% | P23975 |
| SLC6A3 | DAT | Inhibition | 5.42 | 0.2% | Q01959 |
| SLC6A4 | SERT | Inhibition | 6.83 | 0.7% | P31645 |
Broader ChEMBL bioactivity targets: 15 (assay-derived). Sample: Alpha-2A adrenergic receptor, D(1A) dopamine receptor, Thromboxane A2 receptor, Muscarinic acetylcholine receptor M2, 5-hydroxytryptamine receptor 1A, Muscarinic acetylcholine receptor M1, Sodium-dependent noradrenaline transporter, Sodium-dependent serotonin transporter, Alpha-1A adrenergic receptor, Mu-type opioid receptor, D(3) dopamine receptor, Sodium-dependent dopamine transporter, Voltage-gated inwardly rectifying potassium channel KCNH2, Voltage-dependent N-type calcium channel subunit alpha-1B, Solute carrier family 22 member 1.
Bioactivity
ChEMBL activities: 10 potent at pChembl ≥ 5 of 15 total. Top 100 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| DRD3 | 7.75 | AC50 | 17.8 | nM | CHEMBL_ACT_25194772 |
| DRD1 | 6.83 | AC50 | 148.5 | nM | CHEMBL_ACT_25115466 |
| CHRM2 | 6.8 | AC50 | 158.1 | nM | CHEMBL_ACT_25195992 |
| ADRA1A | 6.79 | AC50 | 163.6 | nM | CHEMBL_ACT_25219064 |
| CHRM1 | 6.51 | AC50 | 310.8 | nM | CHEMBL_ACT_25210425 |
| SLC6A4 | 6.24 | AC50 | 578.7 | nM | CHEMBL_ACT_25151583 |
| ADRA2A | 5.9 | AC50 | 1270 | nM | CHEMBL_ACT_25156685 |
| OPRM1 | 5.24 | AC50 | 5695 | nM | CHEMBL_ACT_25158431 |
| KCNH2 | 5.05 | AC50 | 8900 | nM | CHEMBL_ACT_25118123 |
| TBXA2R | 5.02 | AC50 | 9638 | nM | CHEMBL_ACT_25211350 |
Target pathways
Aggregated over 3 target gene(s): SLC6A2, SLC6A3, SLC6A4.
Top Reactome pathways
15 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| SLC-mediated transport of neurotransmitters | 3 | SLC6A2, SLC6A3, SLC6A4 |
| Neurotransmitter clearance | 2 | SLC6A3, SLC6A4 |
| Transmission across Chemical Synapses | 2 | SLC6A3, SLC6A4 |
| Neuronal System | 2 | SLC6A3, SLC6A4 |
| Disease | 2 | SLC6A2, SLC6A3 |
| Transport of small molecules | 2 | SLC6A2, SLC6A3 |
| R-HSA-425366 | 2 | SLC6A2, SLC6A3 |
| SLC-mediated transmembrane transport | 2 | SLC6A2, SLC6A3 |
| SLC transporter disorders | 2 | SLC6A2, SLC6A3 |
| Disorders of transmembrane transporters | 2 | SLC6A2, SLC6A3 |
| Dopamine clearance from the synaptic cleft | 1 | SLC6A3 |
| Serotonin clearance from the synaptic cleft | 1 | SLC6A4 |
| Defective neurotransmitter clearance by SLC6A3 causes Parkinsonism-dystonia infantile (PKDYS) | 1 | SLC6A3 |
| Defective SLC6A2 causes orthostatic intolerance (OI) | 1 | SLC6A2 |
| Defective transport of neurotransmitters by SLC6A3 causes Parkinsonism-dystonia infantile (PKDYS) | 1 | SLC6A3 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| neurotransmitter transport | 3 |
| amino acid transport | 3 |
| response to xenobiotic stimulus | 3 |
| obsolete monoamine transport | 3 |
| sodium ion transmembrane transport | 3 |
| transmembrane transport | 3 |
| dopamine uptake involved in synaptic transmission | 2 |
| norepinephrine uptake | 2 |
| neurotransmitter reuptake | 2 |
| chemical synaptic transmission | 1 |
| obsolete norepinephrine transport | 1 |
| response to pain | 1 |
| neuron cellular homeostasis | 1 |
| catecholamine uptake | 1 |
| chloride transmembrane transport | 1 |
Indications & clinical
Indications
1 approved indication. FDA phase 4, plus an anticancer drug’s labelled cancer uses (which ChEMBL often logs at phase 3).
| Indication | Phase | MONDO | EFO |
|---|---|---|---|
| depressive disorder | 4 | MONDO:0002050 | MONDO:0002050 |
2 diseases in clinical trials (phase 1–3, investigational — not approved indications). Highest ChEMBL trial phase per disease; a non-cancer approved use is occasionally logged at phase 3 here.
| Disease (in trials) | Phase | MONDO | EFO |
|---|---|---|---|
| anxiety | 3 | MONDO:0011918 | EFO:0005230 |
| dementia | 3 | MONDO:0001627 | HP:0000726 |
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 |
|---|---|
| PHASE4 | 1 |
| PHASE3 | 1 |
| PHASE2 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT02237937 | PHASE4 | UNKNOWN | Optimizing Antidepressant Treatment by Genotype-dependent Adjustment of Medication According to the ABCB1 Gene |
| NCT02374567 | PHASE3 | TERMINATED | Pharmacovigilance in Gerontopsychiatric Patients |
| NCT07263438 | PHASE2 | RECRUITING | Efficacy of the Combination of Trimipramine and Atezolizumab With Bevacizumab in Patients With Recurrent Glioblastoma: a Phase 2 Trial |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
PharmGKB dosing guidelines (1) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):
| Guideline | Source | Gene(s) | Dosing | Recommendation |
|---|---|---|---|---|
| Annotation of CPIC Guideline for trimipramine and CYP2C19, CYP2D6 | CPIC | CYP2C19;CYP2D6 | yes | yes |
PharmGKB also curates 3 clinical and 13 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.
664 molecules share ≥1 primary target. Top 100 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| Afatinib | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| AMITRIPTYLINE | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CRIZOTINIB | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| GENTIAN VIOLET | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| Idelalisib | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| Olodaterol | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| PIMAVANSERIN | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| REGORAFENIB | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| Tadalafil | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| TAFENOQUINE | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| UMECLIDINIUM | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| VORAPAXAR | ChEMBL + PubChem | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| ACETOPHENAZINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| AMIODARONE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| AMOXAPINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| ARIPIPRAZOLE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| ASENAPINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| ASTEMIZOLE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| ATOMOXETINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| AZELASTINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| BAZEDOXIFENE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| BENFLUOREX | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| BENZPHETAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| BENZTROPINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| BENZYDAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| BEPRIDIL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| BOSUTINIB | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| BREXPIPRAZOLE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| BROMHEXINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| BROMODIPHENHYDRAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| BROMPERIDOL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| BROMPHENIRAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| BUPROPION | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CABERGOLINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CALCITRIOL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CARBINOXAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CARVEDILOL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CELECOXIB | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CETIRIZINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CHLORHEXIDINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CHLORPHENIRAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CHLORPHENTERMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CHLORPROMAZINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CHLORPROTHIXENE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CINACALCET | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CINNARIZINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CITALOPRAM | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CLEMASTINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CLOMIPHENE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CLOMIPRAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CLOTRIMAZOLE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| COBIMETINIB | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| COCAINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| CYPROHEPTADINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DANAZOL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DAUNORUBICIN | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DEQUALINIUM | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DESIPRAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DESLORATADINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DESOGESTREL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DESVENLAFAXINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DEXBROMPHENIRAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DEXCHLORPHENIRAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DEXTROAMPHETAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DIETHYLSTILBESTROL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DIPHENHYDRAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DOBUTAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DOMPERIDONE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DOTHIEPIN | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DOXAZOSIN | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DRONEDARONE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| DULOXETINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| EBASTINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| ECONAZOLE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| EPALRESTAT | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| ERDAFITINIB | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| ETHINYL ESTRADIOL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| FEDRATINIB | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| FENOLDOPAM | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| FENOTEROL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| FIPEXIDE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| FLUOXETINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| FLUPHENAZINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| FLUSPIRILENE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| FLUVOXAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| GUANABENZ | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| HALOPERIDOL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| HALOPROGIN | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| HEXAFLUORENIUM | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| HEXETIDINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| IDARUBICIN | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| ILOPERIDONE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| IMIPRAMINE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| INDACATEROL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| INDOCYANINE GREEN ACID FORM | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| ISOCONAZOLE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| KETOCONAZOLE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| LABETALOL | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| LASOFOXIFENE | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
| LEVOMILNACIPRAN | ChEMBL | Phase 4 (approved) | SLC6A2, SLC6A3, SLC6A4 |
Related Atlas pages
- Genes: SLC6A2, SLC6A3, SLC6A4
- Indicated for: depressive disorder
- In clinical trials for: anxiety, dementia
- Drugs: Afatinib, Amitriptyline, Crizotinib, Idelalisib, Olodaterol, Pimavanserin, Regorafenib, Tadalafil, Tafenoquine, Umeclidinium, Vorapaxar, Acetophenazine, Amiodarone, Amoxapine, Aripiprazole, Asenapine, Astemizole, Atomoxetine, Azelastine, Bazedoxifene, Benfluorex, Benzphetamine, Benztropine, Benzydamine, Bepridil, Bosutinib, Brexpiprazole, Bromhexine, Bromodiphenhydramine, Bromperidol, Brompheniramine, Bupropion, Cabergoline, Calcitriol, Carbinoxamine, Carvedilol, Celecoxib, Cetirizine, Chlorhexidine, Chlorpheniramine, Chlorphentermine, Chlorpromazine, Chlorprothixene, Cinacalcet, Cinnarizine, Citalopram, Clemastine, Clomiphene, Clomipramine, Clotrimazole, Cobimetinib, Cocaine, Cyproheptadine, Danazol, Daunorubicin, Dequalinium, Desipramine, Desloratadine, Desogestrel, Desvenlafaxine, Dexbrompheniramine, Dextroamphetamine, Diethylstilbestrol, Diphenhydramine, Dobutamine, Domperidone, Dothiepin, Doxazosin, Dronedarone, Duloxetine, Ebastine, Econazole, Epalrestat, Erdafitinib, Ethinyl Estradiol, Fedratinib, Fenoldopam, Fenoterol, Fipexide, Fluoxetine, Fluphenazine, Fluspirilene, Fluvoxamine, Guanabenz, Haloperidol, Haloprogin, Hexafluorenium, Hexetidine, Idarubicin, Iloperidone, Imipramine, Indacaterol, Indocyanine Green Acid Form, Isoconazole, Ketoconazole, Labetalol, Lasofoxifene, Levomilnacipran