Levallorphan
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Also known as LevallorphaneLevalorfanoNaloxiphanLevellorphanSID144205558SID170465778Levallorphan tartrate
Summary
Levallorphan (CHEMBL1254682) is an approved small molecule targeting OPRM1.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- Targets: 1 (OPRM1)
- Chemistry: 283.4 Da · C19H25NO
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1254682 |
| Name | Levallorphan |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 5359371 |
| Molecular formula | C19H25NO |
| Molecular weight | 283.4 |
| InChIKey | OZYUPQUCAUTOBP-QXAKKESOSA-N |
SMILES: C=CCN1CC[C@]23CCCC[C@H]2[C@H]1CC4=C3C=C(C=C4)O
IUPAC name: (1R,9R,10R)-17-prop-2-enyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-trien-4-ol
Also known as: Levallorphan, Levallorphane, Levalorfano, Naloxiphan, levallorphan, Levellorphan, SID144205558, SID170465778, Levallorphan tartrate, LEVALLORPHAN
Parent form; salt/anhydrous children: CHEMBL2062276
Patent coverage: 1,672 distinct patent families (7,151 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 7,108 (99%) 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 |
|---|---|---|---|---|---|
| OPRM1 | μ receptor | Antagonist | 9.32 | 0% | P35372 |
Broader ChEMBL bioactivity targets: 11 (assay-derived). Sample: Opioid receptor, Opioid receptors; mu & kappa, Muscarinic acetylcholine receptor M2, 5-hydroxytryptamine receptor 1A, Acetylcholinesterase, Prostaglandin G/H synthase 1, Mu-type opioid receptor, D(3) dopamine receptor, Voltage-gated inwardly rectifying potassium channel KCNH2, Mu-type opioid receptor.
Bioactivity
ChEMBL activities: 11 potent at pChembl ≥ 5 of 16 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| OPRM1 | 9.32 | Ki | 0.48 | nM | CHEMBL_ACT_6262899 |
| P33533 | 9.27 | IC50 | 0.54 | nM | CHEMBL_ACT_1248408 |
| P33535 | 9.2 | IC50 | 0.63 | nM | CHEMBL_ACT_6357148 |
| OPRM1 | 9.17 | IC50 | 0.67 | nM | CHEMBL_ACT_1248410 |
| P33533 | 8.96 | IC50 | 1.1 | nM | CHEMBL_ACT_1248407 |
| OPRM1 | 8.89 | Ki | 1.29 | nM | CHEMBL_ACT_6262887 |
| OPRM1 | 8.77 | Ki | 1.69 | nM | CHEMBL_ACT_6262893 |
| OPRM1 | 8.59 | IC50 | 2.6 | nM | CHEMBL_ACT_1248411 |
| OPRM1 | 8.52 | AC50 | 3 | nM | CHEMBL_ACT_25158252 |
| PTGS1 | 5.07 | AC50 | 8536 | nM | CHEMBL_ACT_25205301 |
| CHRM2 | 5.05 | AC50 | 8914 | nM | CHEMBL_ACT_25195813 |
Target pathways
Aggregated over 1 target gene(s): OPRM1.
Top Reactome pathways
6 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Opioid Signalling | 1 | OPRM1 |
| G-protein activation | 1 | OPRM1 |
| Peptide ligand-binding receptors | 1 | OPRM1 |
| G alpha (i) signalling events | 1 | OPRM1 |
| Interleukin-4 and Interleukin-13 signaling | 1 | OPRM1 |
| MECP2 regulates neuronal receptors and channels | 1 | OPRM1 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| G protein-coupled receptor signaling pathway | 1 |
| G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger | 1 |
| adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway | 1 |
| adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathway | 1 |
| phospholipase C-activating G protein-coupled receptor signaling pathway | 1 |
| neuropeptide signaling pathway | 1 |
| sensory perception | 1 |
| negative regulation of cell population proliferation | 1 |
| sensory perception of pain | 1 |
| G protein-coupled opioid receptor signaling pathway | 1 |
| negative regulation of nitric oxide biosynthetic process | 1 |
| behavioral response to ethanol | 1 |
| positive regulation of neurogenesis | 1 |
| negative regulation of cytosolic calcium ion concentration | 1 |
| negative regulation of Wnt protein secretion | 1 |
Indications & clinical
Indications
0 indications (0 at ChEMBL trial phase 4).
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.
400 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| Dihydroergotamine | ChEMBL + PubChem | Phase 4 (approved) | OPRM1 |
| ELUXADOLINE | ChEMBL + PubChem | Phase 4 (approved) | OPRM1 |
| GENTIAN VIOLET | ChEMBL + PubChem | Phase 4 (approved) | OPRM1 |
| MAVORIXAFOR | ChEMBL + PubChem | Phase 4 (approved) | OPRM1 |
| PIMAVANSERIN | ChEMBL + PubChem | Phase 4 (approved) | OPRM1 |
| PROPOXYPHENE | ChEMBL + PubChem | Phase 4 (approved) | OPRM1 |
| REGORAFENIB | ChEMBL + PubChem | Phase 4 (approved) | OPRM1 |
| VORAPAXAR | ChEMBL + PubChem | Phase 4 (approved) | OPRM1 |
| ALFENTANIL | ChEMBL | Phase 4 (approved) | OPRM1 |
| ALOGLIPTIN | ChEMBL | Phase 4 (approved) | OPRM1 |
| ALPIDEM | ChEMBL | Phase 4 (approved) | OPRM1 |
| ALVIMOPAN | ChEMBL | Phase 4 (approved) | OPRM1 |
| AMBENONIUM | ChEMBL | Phase 4 (approved) | OPRM1 |
| AMILORIDE | ChEMBL | Phase 4 (approved) | OPRM1 |
| AMIODARONE | ChEMBL | Phase 4 (approved) | OPRM1 |
| AMITRIPTYLINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| AMLODIPINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| AMODIAQUINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| AMOXAPINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| ANTAZOLINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| ARIPIPRAZOLE | ChEMBL | Phase 4 (approved) | OPRM1 |
| ASTEMIZOLE | ChEMBL | Phase 4 (approved) | OPRM1 |
| ATOMOXETINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| AZELASTINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| BAZEDOXIFENE | ChEMBL | Phase 4 (approved) | OPRM1 |
| BENFLUOREX | ChEMBL | Phase 4 (approved) | OPRM1 |
| BENZBROMARONE | ChEMBL | Phase 4 (approved) | OPRM1 |
| BENZIODARONE | ChEMBL | Phase 4 (approved) | OPRM1 |
| BENZTROPINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| BENZYDAMINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| BEPRIDIL | ChEMBL | Phase 4 (approved) | OPRM1 |
| BEXAROTENE | ChEMBL | Phase 4 (approved) | OPRM1 |
| BITHIONOL | ChEMBL | Phase 4 (approved) | OPRM1 |
| BOSUTINIB | ChEMBL | Phase 4 (approved) | OPRM1 |
| BROMOCRIPTINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| BROMODIPHENHYDRAMINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| BROMPERIDOL | ChEMBL | Phase 4 (approved) | OPRM1 |
| BUPRENORPHINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| BUTORPHANOL | ChEMBL | Phase 4 (approved) | OPRM1 |
| CANDESARTAN CILEXETIL | ChEMBL | Phase 4 (approved) | OPRM1 |
| CANNABIDIOL | ChEMBL | Phase 4 (approved) | OPRM1 |
| CARVEDILOL | ChEMBL | Phase 4 (approved) | OPRM1 |
| CASPOFUNGIN | ChEMBL | Phase 4 (approved) | OPRM1 |
| CETRORELIX | ChEMBL | Phase 4 (approved) | OPRM1 |
| CHLORHEXIDINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| CHLORPROMAZINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| CHLORPROTHIXENE | ChEMBL | Phase 4 (approved) | OPRM1 |
| CINACALCET | ChEMBL | Phase 4 (approved) | OPRM1 |
| CINNARIZINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| CITALOPRAM | ChEMBL | Phase 4 (approved) | OPRM1 |
| CLEMASTINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| CLOMIPHENE | ChEMBL | Phase 4 (approved) | OPRM1 |
| CLOMIPRAMINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| CLOPIDOGREL | ChEMBL | Phase 4 (approved) | OPRM1 |
| CLOTRIMAZOLE | ChEMBL | Phase 4 (approved) | OPRM1 |
| COBIMETINIB | ChEMBL | Phase 4 (approved) | OPRM1 |
| CODEINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| CYCLIZINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| CYPROHEPTADINE | ChEMBL | Phase 4 (approved) | OPRM1 |
| DANAZOL | ChEMBL | Phase 4 (approved) | OPRM1 |
Related Atlas pages
- Genes: OPRM1
- Drugs: Dihydroergotamine, Eluxadoline, Mavorixafor, Pimavanserin, Propoxyphene, Regorafenib, Vorapaxar, Alfentanil, Alogliptin, Alpidem, Alvimopan, Ambenonium, Amiloride, Amiodarone, Amitriptyline, Amlodipine, Amodiaquine, Amoxapine, Antazoline, Aripiprazole, Astemizole, Atomoxetine, Azelastine, Bazedoxifene, Benfluorex, Benzbromarone, Benziodarone, Benztropine, Benzydamine, Bepridil, Bexarotene, Bithionol, Bosutinib, Bromocriptine, Bromodiphenhydramine, Bromperidol, Buprenorphine, Butorphanol, Candesartan Cilexetil, Cannabidiol, Carvedilol, Caspofungin, Cetrorelix, Chlorhexidine, Chlorpromazine, Chlorprothixene, Cinacalcet, Cinnarizine, Citalopram, Clemastine, Clomiphene, Clomipramine, Clopidogrel, Clotrimazole, Cobimetinib, Codeine, Cyclizine, Cyproheptadine, Danazol