Ephedrine
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Also known as (-)-ephedrineanhydrousEphedrinumL-ephedrineNSC-170951NSC-8971XenadrineSID124892369(1R,2S)-(-)-ephedrinePSEUDOEPHEDRINE HYDROCHLORIDEEPHEDRINE HYDROCHLORIDEEPHEDRINE (1R;2S) HYDROCHLORIDE
Summary
Ephedrine (CHEMBL211456) is an approved small-molecule sympathomimetic agent (ATC C01CA26) targeting ADRB2; indicated across 9 conditions including obesity disorder and cardiovascular disorder.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: C01CA26 (+4 more)
- Targets: 1 (ADRB2)
- Indications: 9 conditions
- Clinical trials: 89
- Chemistry: 165.23 Da · C10H15NO
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL211456 |
| Name | Ephedrine |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 9294 |
| ChEBI | CHEBI:15407 |
| ATC | C01CA26, R01AB05, A08AA56, R01AA03, S01FB02 |
| Molecular formula | C10H15NO |
| Molecular weight | 165.23 |
| InChIKey | KWGRBVOPPLSCSI-WPRPVWTQSA-N |
SMILES: C[C@@H]([C@@H](C1=CC=CC=C1)O)NC
IUPAC name: (1R,2S)-2-(methylamino)-1-phenylpropan-1-ol
ChEBI definition: A phenethylamine alkaloid that is 2-phenylethanamine substituted by a methyl group at the amino nitrogen and a methyl and a hydroxy group at position 2 and 1 respectively.
Pharmacological roles (ChEBI): nasal decongestant, sympathomimetic agent, vasoconstrictor agent.
Other ChEBI roles (chemical / environmental): xenobiotic, environmental contaminant, plant metabolite, bacterial metabolite.
Also known as: (-)-ephedrine, Ephedrine, anhydrous, Ephedrinum, L-ephedrine, NSC-170951, NSC-8971, Xenadrine, ephedrine, SID124892369, (1R,2S)-(-)-ephedrine, EPHEDRINE
Parent form; salt/anhydrous children: CHEMBL526872, CHEMBL1523964, CHEMBL2146102
Patent coverage: 14,540 distinct patent families (43,915 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 43,914 (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 |
|---|---|---|---|---|---|
| ADRB2 | β2-adrenoceptor | Partial agonist | 5.6 | 0.4% | P07550 |
Broader ChEMBL bioactivity targets: 2 (assay-derived). Sample: Muscarinic acetylcholine receptor M2, Alpha-1A adrenergic receptor.
Bioactivity
No ChEMBL bioactivity rows at pChembl ≥ 5 (expected for biologics / antibodies).
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
9 indications (3 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 |
|---|---|---|---|
| obesity disorder | 4 | MONDO:0011122 | EFO:0001073 |
| cardiovascular disorder | 4 | MONDO:0004995 | EFO:0000319 |
| hypotensive disorder | 3 | MONDO:0005468 | EFO:0005251 |
| preeclampsia | 3 | MONDO:0005081 | EFO:0000668 |
| blood coagulation disease | 2 | MONDO:0001531 | EFO:0009314 |
4 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 89.
Phase distribution
| Phase | Trials |
|---|---|
| Not specified | 38 |
| PHASE4 | 27 |
| PHASE3 | 8 |
| PHASE2 | 7 |
| PHASE2/PHASE3 | 4 |
| PHASE1 | 3 |
| PHASE1/PHASE2 | 2 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT05873218 | PHASE4 | RECRUITING | Impact of Prophylactic Ephedrine on Fetal Heart Tracing and Uterine Tetanic Contraction After CSE |
| NCT06257316 | PHASE4 | NOT_YET_RECRUITING | Appropriate Dosage of Vasopressor in Neonates and Infants |
| NCT06681662 | PHASE4 | RECRUITING | Ephedrine for Reducing Onset Time of Rocurinium in Elderly Patients |
| NCT07322419 | PHASE4 | RECRUITING | Hemodynamics During Cesarean Delivery Under Spinal Anesthesia With Norepinephrine Versus Ephedrine |
| NCT07379710 | PHASE4 | NOT_YET_RECRUITING | Norepinephrine With Ephedrine Versus Norepinephrine Alone During Spinal Anesthesia for Cesarean Delivery |
| NCT00991627 | PHASE4 | COMPLETED | Different Approaches to Maternal Hypotension During Cesarean Section |
| NCT01243970 | PHASE4 | TERMINATED | Ephedrine vs Phenylephrine - ECG Changes |
| NCT01509521 | PHASE4 | COMPLETED | The Oxygenation of the Brain During Caesarean Section |
| NCT01794273 | PHASE4 | COMPLETED | Compared Efficacy and Tolerance of Two Vasopressors Used to Treat Preoperative Hypotension During Carotid Surgery |
| NCT02025426 | PHASE4 | TERMINATED | Phenylephrine Versus Ephedrine in Pre-eclampsia |
| NCT02062801 | PHASE4 | COMPLETED | Prophylactic Ephedrine and Combined Spinal Epidurals for Labor |
| NCT02327923 | PHASE4 | COMPLETED | Intraoperative Lidocaine Infusion vs. Esmolol Infusion for Postoperative Analgesia in Laparoscopic Cholecystectomy |
| NCT02477501 | PHASE4 | COMPLETED | Ephedrine vs. Nor Epinephrine Infusion in Preventing Hypotension After Spinal Anesthesia for Cesarean Section |
| NCT02522858 | PHASE4 | COMPLETED | Anticholinergic Premedication for Sedation With Dexmedetomidine During Spinal Anesthesia |
| NCT02713087 | PHASE4 | COMPLETED | Vasopressor Effects in Anesthetized Patients |
| NCT03704909 | PHASE4 | COMPLETED | Manging Post Spinal Hypotension During Elective Cesarean Section |
| NCT03719625 | PHASE4 | UNKNOWN | Norepinephrine Versus Ephedrin for Prevention of Post Spinal Anesthesia in Cesarean Section |
| NCT03767296 | PHASE4 | COMPLETED | Influence of a Bolus Administration of Ephedrine and Phenylephrine on the Spinal Oxygen Saturation, Measured With NIRS. |
| NCT03864094 | PHASE4 | COMPLETED | Hemodynamics During Induction of General Anesthesia After Prophylactic Ephedrine, Phenylephrine or Norepinephrine. |
| NCT03984526 | PHASE4 | COMPLETED | Atropine or Ephedrine Pretreatment for Preventing Bradycardia in Elderly Patients |
| NCT05127876 | PHASE4 | COMPLETED | Ephedrine Versus Ondansetron During Cesarean Delivery |
| NCT05498857 | PHASE4 | UNKNOWN | Intramuscular Ephedrine in the Prevention of Hypotension in Patients Undergoing Spinal Anesthesia |
| NCT05892913 | PHASE4 | COMPLETED | The Effect of Low-dose Atropine on Sympathetic Blockade in Spinal Cesarean Section Patients |
| NCT05941494 | PHASE4 | UNKNOWN | Cerebral Flow-metabolism Coupling During Adult Surgery |
| NCT05993182 | PHASE4 | COMPLETED | Comparative Study Among Different Doses of Ephedrine During Elective Cesarean Section Under Subarachnoid Block. |
| NCT06668337 | PHASE4 | COMPLETED | Ephedrine Doses to Prevent Maternal Hypotension After Spinal Anesthesia in Cesarean Section |
| NCT06921473 | PHASE4 | COMPLETED | Effect of Ephedrine vs. Norepinephrine on Prevention of Fetal Acidosis During Cesarean Section Under Spinal Anesthesia |
| NCT00146926 | PHASE3 | UNKNOWN | Comparison of Three Different Strategies to Prevent Propofol Induced Pain During Infusion |
| NCT01451060 | PHASE3 | WITHDRAWN | Maternal and Neonatal Outcomes of the Use of Vasopressors to Treat Hypotension During Spinal Anesthesia for Cesarean |
| NCT01858090 | PHASE3 | COMPLETED | Intrathecal Levobupivacaine With Opioids for Caesarean Section |
| NCT02048215 | PHASE3 | COMPLETED | Effect on Energy Metabolism at Cellular Level of Diet Plus Treatment With Ephedrine and Caffeine in Obesity |
| NCT02277730 | PHASE2/PHASE3 | COMPLETED | A Novel Closed-loop Integrated System for the Maintenance of Haemodynamic Stability |
| NCT02428062 | PHASE2/PHASE3 | SUSPENDED | Target Hemodynamics and Brain Injury During General Anesthesia in the Elderly |
| NCT02658721 | PHASE3 | COMPLETED | Effects of Systemic or Adjunct Tramadol Addition to Lidocaine Used for IVRA in Patients Undergoing Hand Surgery |
| NCT03047109 | PHASE2/PHASE3 | COMPLETED | Ephedrine and Phenylephrine for Spinal Hypotension |
| NCT04025918 | PHASE2/PHASE3 | COMPLETED | Closed-loop Double-vasopressor Automated System to Treat Hypotension During Spinal Anaesthesia for Caesarean Section |
| NCT05276596 | PHASE3 | COMPLETED | Evaluation of the Early Use of Norepinephrine in Major Abdominal Surgery on Postoperative Organ Dysfunction |
| NCT05497700 | PHASE3 | UNKNOWN | Comparative Efficacity of Ephedrine Versus Norepinephrine to Correct Anesthesia Induction Related Hypotension |
| NCT05725031 | PHASE3 | COMPLETED | Intubation Conditions After RSI Using Rocuronium with Ephedrine Pretreatment |
| NCT00000752 | PHASE2 | WITHDRAWN | Preventing Frequent Sinus Infections in HIV-Infected Patients |
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.
189 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 |
| METAPROTERENOL | 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 |
Related Atlas pages
- Genes: ADRB2
- Diseases: obesity disorder, cardiovascular disorder, hypotensive disorder, preeclampsia
- 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, Metaproterenol, Metoprolol, Mifepristone, Montelukast, Nadolol, Nebivolol, Nitazoxanide