Levonordefrin
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Also known as (-)-cobefrinBA 2818BA-2818CorbadrinaCorbadrineL-.alpha.-methylnoradrenalineL-nordefrinNeo-cobefrinNordefrin (-)-formNordefrinl-NSC-757084SID11111073SID11112447SID170464794SID144205604
Summary
Levonordefrin (CHEMBL677) is an approved small-molecule α-adrenergic agonist targeting ADRA1D.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- Targets: 1 (ADRA1D)
- Clinical trials: 1
- Chemistry: 183.2 Da · C9H13NO3
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL677 |
| Name | Levonordefrin |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 164739 |
| ChEBI | CHEBI:141146 |
| Molecular formula | C9H13NO3 |
| Molecular weight | 183.2 |
| InChIKey | GEFQWZLICWMTKF-CDUCUWFYSA-N |
SMILES: C[C@@H]([C@@H](C1=CC(=C(C=C1)O)O)O)N
IUPAC name: 4-[(1R,2S)-2-amino-1-hydroxypropyl]benzene-1,2-diol
ChEBI definition: A catecholamine in which the 2-aminoethyl group is substituted with a hydroxy group at C-1 and a methyl group at C-2, with configurations 1R,2S. A metabolite of α-methyl-L-dopa, it is an alpha2-adrenergic agonist and acts as a topical nasal decongestant and vasoconstrictor, most often used in dentistry.
Pharmacological roles (ChEBI): α-adrenergic agonist, vasoconstrictor agent, nasal decongestant.
Also known as: (-)-cobefrin, BA 2818, BA-2818, Corbadrina, Corbadrine, L-.alpha.-methylnoradrenaline, L-nordefrin, Levonordefrin, Neo-cobefrin, Nordefrin (-)-form, Nordefrin, l-
Patent coverage: 369 distinct patent families (1,187 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 1,175 (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 |
|---|---|---|---|---|---|
| ADRA1D | α1D-adrenoceptor | Full agonist | 5.6 | 0.2% | P25100 |
Broader ChEMBL bioactivity targets: 15 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Lysine-specific demethylase 4E, Fructose-bisphosphate aldolase, Prelamin-A/C, ATP-dependent DNA helicase Q1, 4’-phosphopantetheinyl transferase ffp, Thrombopoietin, Adrenergic receptor alpha-1, Thyrotropin receptor, Adrenergic receptor alpha-2.
Bioactivity
ChEMBL activities: 21 potent at pChembl ≥ 5 of 29 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| P19328 | 8.11 | Ki | 7.7 | nM | CHEMBL_ACT_538350 |
| HSD17B10 | 7 | Potency | 100 | nM | CHEMBL_ACT_4829625 |
| P19328 | 6.69 | Ki | 205 | nM | CHEMBL_ACT_1038577 |
| LMNA | 6.6 | Potency | 251.2 | nM | CHEMBL_ACT_3667018 |
| TDP1 | 6.45 | Potency | 354.8 | nM | CHEMBL_ACT_3931858 |
| HIF1A | 6.3 | Potency | 501.2 | nM | CHEMBL_ACT_4128014 |
| HIF1A | 6.3 | Potency | 501.2 | nM | CHEMBL_ACT_4520623 |
| P15823 | 6.11 | EC50 | 776 | nM | CHEMBL_ACT_476429 |
| HSD17B10 | 6 | Potency | 1000 | nM | CHEMBL_ACT_4821724 |
| RECQL | 5.75 | Potency | 1778 | nM | CHEMBL_ACT_3699840 |
| Q27686 | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_3692503 |
| Q27686 | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_3701131 |
| HSD17B10 | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_3710966 |
| HIF1A | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_4127984 |
| ALOX15 | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_4468824 |
| HIF1A | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_4520593 |
| P15823 | 5.44 | Ki | 3600 | nM | CHEMBL_ACT_1110175 |
| KDM4E | 5.35 | Potency | 4467 | nM | CHEMBL_ACT_3746771 |
| A8B2U2 | 5.15 | Potency | 7063 | nM | CHEMBL_ACT_4600137 |
| P15823 | 5.14 | Ki | 7300 | nM | CHEMBL_ACT_1124590 |
| P15823 | 5.04 | Ki | 9221 | nM | CHEMBL_ACT_1038576 |
Target pathways
Aggregated over 1 target gene(s): ADRA1D.
Top Reactome pathways
9 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Signal Transduction | 1 | ADRA1D |
| Signaling by GPCR | 1 | ADRA1D |
| Class A/1 (Rhodopsin-like receptors) | 1 | ADRA1D |
| Amine ligand-binding receptors | 1 | ADRA1D |
| GPCR downstream signalling | 1 | ADRA1D |
| Adrenoceptors | 1 | ADRA1D |
| G alpha (q) signalling events | 1 | ADRA1D |
| G alpha (12/13) signalling events | 1 | ADRA1D |
| GPCR ligand binding | 1 | ADRA1D |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| G protein-coupled receptor signaling pathway | 1 |
| adenylate cyclase-modulating G protein-coupled receptor signaling pathway | 1 |
| phospholipase C-activating G protein-coupled receptor signaling pathway | 1 |
| positive regulation of cytosolic calcium ion concentration | 1 |
| cell-cell signaling | 1 |
| positive regulation of cell population proliferation | 1 |
| positive regulation of MAPK cascade | 1 |
| positive regulation of vasoconstriction | 1 |
| adenylate cyclase-activating adrenergic receptor signaling pathway | 1 |
| neuron-glial cell signaling | 1 |
| signal transduction | 1 |
| adrenergic receptor signaling pathway | 1 |
Indications & clinical
Indications
0 indications (0 at ChEMBL trial phase 4).
Clinical trials
Total trials: 1.
Phase distribution
| Phase | Trials |
|---|---|
| Not specified | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT05875519 | Not specified | COMPLETED | Healing Process and Blood Sugar Level Following Local Anesthetic Infiltration With and Without Vasoconstrictor |
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.
122 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| DIHYDROERGOTAMINE | ChEMBL + PubChem | Phase 4 (approved) | ADRA1D |
| ALFUZOSIN | ChEMBL | Phase 4 (approved) | ADRA1D |
| AMITRIPTYLINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| AMLODIPINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| AMOXAPINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| APOMORPHINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| APRACLONIDINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| ARIPIPRAZOLE | ChEMBL | Phase 4 (approved) | ADRA1D |
| ASENAPINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| ASTEMIZOLE | ChEMBL | Phase 4 (approved) | ADRA1D |
| ATENOLOL | ChEMBL | Phase 4 (approved) | ADRA1D |
| ATROPINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| AZELASTINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| BENZTROPINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| BREXPIPRAZOLE | ChEMBL | Phase 4 (approved) | ADRA1D |
| BRIMONIDINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| BROMOCRIPTINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| BUSPIRONE | ChEMBL | Phase 4 (approved) | ADRA1D |
| CARIPRAZINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| CARVEDILOL | ChEMBL | Phase 4 (approved) | ADRA1D |
| CHLORPROMAZINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| CINNARIZINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| CISAPRIDE | ChEMBL | Phase 4 (approved) | ADRA1D |
| CITALOPRAM | ChEMBL | Phase 4 (approved) | ADRA1D |
| CLEMASTINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| CLOMIPRAMINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| CLONIDINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| CLOTRIMAZOLE | ChEMBL | Phase 4 (approved) | ADRA1D |
| CLOZAPINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| CYCLIZINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| CYPROHEPTADINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| DAPIPRAZOLE | ChEMBL | Phase 4 (approved) | ADRA1D |
| DEXCHLORPHENIRAMINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| DEXMEDETOMIDINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| DIETHYLSTILBESTROL | ChEMBL | Phase 4 (approved) | ADRA1D |
| DIMENHYDRINATE | ChEMBL | Phase 4 (approved) | ADRA1D |
| DOBUTAMINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| DOMPERIDONE | ChEMBL | Phase 4 (approved) | ADRA1D |
| DOPAMINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| DOXAZOSIN | ChEMBL | Phase 4 (approved) | ADRA1D |
| DOXEPIN | ChEMBL | Phase 4 (approved) | ADRA1D |
| DROPERIDOL | ChEMBL | Phase 4 (approved) | ADRA1D |
| EBASTINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| ECONAZOLE | ChEMBL | Phase 4 (approved) | ADRA1D |
| EPINEPHRINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| ERGOTAMINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| FENOLDOPAM | ChEMBL | Phase 4 (approved) | ADRA1D |
| FLUPHENAZINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| GENTIAN VIOLET | ChEMBL | Phase 4 (approved) | ADRA1D |
| GUANABENZ | ChEMBL | Phase 4 (approved) | ADRA1D |
| GUANFACINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| HALOPERIDOL | ChEMBL | Phase 4 (approved) | ADRA1D |
| HYDROXYCHLOROQUINE | ChEMBL | Phase 4 (approved) | ADRA1D |
| IMIQUIMOD | ChEMBL | Phase 4 (approved) | ADRA1D |
| INDACATEROL | ChEMBL | Phase 4 (approved) | ADRA1D |
| INDORAMIN | ChEMBL | Phase 4 (approved) | ADRA1D |
| ISOPROTERENOL | ChEMBL | Phase 4 (approved) | ADRA1D |
| KETOTIFEN | ChEMBL | Phase 4 (approved) | ADRA1D |
| LABETALOL | ChEMBL | Phase 4 (approved) | ADRA1D |
| MAPROTILINE | ChEMBL | Phase 4 (approved) | ADRA1D |
Related Atlas pages
- Genes: ADRA1D
- Drugs: Dihydroergotamine, Alfuzosin, Amitriptyline, Amlodipine, Amoxapine, Apomorphine, Apraclonidine, Aripiprazole, Asenapine, Astemizole, Atenolol, Atropine, Azelastine, Benztropine, Brexpiprazole, Brimonidine, Bromocriptine, Buspirone, Cariprazine, Carvedilol, Chlorpromazine, Cinnarizine, Cisapride, Citalopram, Clemastine, Clomipramine, Clonidine, Clotrimazole, Clozapine, Cyclizine, Cyproheptadine, Dapiprazole, Dexchlorpheniramine, Dexmedetomidine, Diethylstilbestrol, Dimenhydrinate, Dobutamine, Domperidone, Dopamine, Doxazosin, Doxepin, Droperidol, Ebastine, Econazole, Epinephrine, Ergotamine, Fenoldopam, Fluphenazine, Guanabenz, Guanfacine, Haloperidol, Hydroxychloroquine, Imiquimod, Indacaterol, Indoramin, Isoproterenol, Ketotifen, Labetalol, Maprotiline