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Phenylephrine

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Also known as (-)-phenylephrine(r)-phenylephrineAB-101 (PHENYLEPHRINE)CyclomydrilDuo-medihalerFenilefrinaJ8.601KM-oxedrineM-sympatholM-sympatolM-synephrineMeta-synephrineMetasynephrinePhenylephrine minimsPhenylephrine, (r)-R(-)-mezatonSID11111644SID90340906L-PHENYLEPHRINE

Summary

Phenylephrine (CHEMBL1215) is an approved small-molecule α-adrenergic agonist (ATC R01AA04) targeting ADRA1A, ADRA1B, and ADRA1D; indicated across 31 conditions including cardiovascular disorder and eye allergy.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: R01AA04 (+8 more)
  • Targets: 3 (ADRA1A, ADRA1B, ADRA1D)
  • Indications: 31 conditions
  • Clinical trials: 186
  • Chemistry: 167.2 Da · C9H13NO2

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL1215
NamePhenylephrine
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID6041
ChEBICHEBI:8093
ATCR01AA04, R01BA53, R01BA03, S01FB01, S01GA05, C01CA06, S01GA55, C05AX06, R01AB01
Molecular formulaC9H13NO2
Molecular weight167.2
InChIKeySONNWYBIRXJNDC-VIFPVBQESA-N

SMILES: CNC[C@@H](C1=CC(=CC=C1)O)O

IUPAC name: 3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol

ChEBI definition: A member of the class of the class of phenylethanolamines that is (1R)-2-(methylamino)-1-phenylethan-1-ol carrying an additional hydroxy substituent at position 3 on the phenyl ring.

Pharmacological roles (ChEBI): α-adrenergic agonist, cardiotonic drug, mydriatic agent, protective agent, vasoconstrictor agent, sympathomimetic agent, nasal decongestant.

Also known as: (-)-phenylephrine, (r)-phenylephrine, AB-101 (PHENYLEPHRINE), Cyclomydril, Duo-medihaler, Fenilefrina, J8.601K, M-oxedrine, M-sympathol, M-sympatol, M-synephrine, Meta-synephrine

Parent form; salt/anhydrous children: CHEMBL1200339, CHEMBL2062264

Patent coverage: 11,190 distinct patent families (37,782 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 37,671 (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).

GeneTargetActionpAffinityCancer dependencyUniProt
ADRA1Aα1A-adrenoceptorFull agonist8.3P35348
ADRA1Bα1B-adrenoceptorAgonist3.90%P35368
ADRA1Dα1D-adrenoceptorFull agonist4.70.2%P25100

Broader ChEMBL bioactivity targets: 26 (assay-derived). Sample: Ras-related protein Rab-9A, Alpha-2A adrenergic receptor, Adrenergic receptor alpha-1, Alpha-2C adrenergic receptor, Alpha-2B adrenergic receptor, Thyrotropin receptor, D(1A) dopamine receptor, Adrenergic receptor alpha-2, Adrenergic receptor beta, Adrenergic receptor alpha-2.

Bioactivity

ChEMBL activities: 46 potent at pChembl ≥ 5 of 53 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
ADRA1B9.07EC500.86nMCHEMBL_ACT_16764916
ADRA1A8.55AC502.8nMCHEMBL_ACT_25229622
ADRA1A8.38AC504.2nMCHEMBL_ACT_25208475
ADRA1B8.23EC505.9nMCHEMBL_ACT_15186180
P181308.05EC509nMCHEMBL_ACT_16896949
ADRA1A7.26EC5055nMCHEMBL_ACT_15186179
ADRA1A7.25EC5055.99nMCHEMBL_ACT_16764854
P193287.11IC5078nMCHEMBL_ACT_1268733
P239446.81EC50154.9nMCHEMBL_ACT_143192
P239446.79Ki162.2nMCHEMBL_ACT_143183
HIF1A6.6Potency251.2nMCHEMBL_ACT_4117732
HIF1A6.6Potency251.2nMCHEMBL_ACT_4519783
P193286.57Ki270nMCHEMBL_ACT_524944
ADRA2A6.51EC50306nMCHEMBL_ACT_16896929
ADRA2C6.47EC50340nMCHEMBL_ACT_16896939
P193286.41Ki390nMCHEMBL_ACT_1018774
ADRA2A6.41Ki390nMCHEMBL_ACT_419870
ADRA2A6.32EC50476.6nMCHEMBL_ACT_25751160
P193286.28IC50520nMCHEMBL_ACT_164140
ADRA2A6.19AC50639.6nMCHEMBL_ACT_25156368
ADRA2A6.05AC50890nMCHEMBL_ACT_25157068
P181306.03Ki933.2nMCHEMBL_ACT_143181
P431406.01Ki977.2nMCHEMBL_ACT_143180
HTR75.96Ki1110nMCHEMBL_ACT_25740732
P188415.9Ki1259nMCHEMBL_ACT_143182
HTR1A5.88AC501310nMCHEMBL_ACT_25164963
ADRA2A5.8AC501600nMCHEMBL_ACT_25219669
P431405.78EC501660nMCHEMBL_ACT_143186
P158235.7IC502000nMCHEMBL_ACT_164139
ADRA2A5.64AC502268nMCHEMBL_ACT_25155871

Target pathways

Aggregated over 3 target gene(s): ADRA1A, ADRA1B, ADRA1D.

Top Reactome pathways

9 total, by targets touching each:

PathwayTargetsGenes
Signal Transduction3ADRA1A, ADRA1B, ADRA1D
Signaling by GPCR3ADRA1A, ADRA1B, ADRA1D
Class A/1 (Rhodopsin-like receptors)3ADRA1A, ADRA1B, ADRA1D
Amine ligand-binding receptors3ADRA1A, ADRA1B, ADRA1D
GPCR downstream signalling3ADRA1A, ADRA1B, ADRA1D
Adrenoceptors3ADRA1A, ADRA1B, ADRA1D
G alpha (q) signalling events3ADRA1A, ADRA1B, ADRA1D
G alpha (12/13) signalling events3ADRA1A, ADRA1B, ADRA1D
GPCR ligand binding3ADRA1A, ADRA1B, ADRA1D

Dominant GO biological processes

GO termTargets
signal transduction3
G protein-coupled receptor signaling pathway3
phospholipase C-activating G protein-coupled receptor signaling pathway3
positive regulation of cytosolic calcium ion concentration3
cell-cell signaling3
positive regulation of MAPK cascade3
adenylate cyclase-activating adrenergic receptor signaling pathway3
neuron-glial cell signaling3
adrenergic receptor signaling pathway3
positive regulation of cardiac muscle hypertrophy2
intracellular signal transduction2
positive regulation of vasoconstriction2
regulation of muscle contraction2
regulation of vasoconstriction2
regulation of cardiac muscle contraction2

Indications & clinical

Indications

31 indications (4 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).

IndicationTrial phaseMONDOEFO
cardiovascular disorder4MONDO:0004995EFO:0000319
eye allergy4MONDO:0005551EFO:0005751
hemorrhoid4MONDO:0004872EFO:0009552
stroke disorder3MONDO:0005098EFO:0000712
seasonal allergic rhinitis3MONDO:0005324EFO:0003956
eye disorder3MONDO:0005328EFO:0003966
hypotensive disorder3MONDO:0005468EFO:0005251
common cold3MONDO:0005709EFO:0007214
influenza3MONDO:0005812EFO:0007328
respiratory tract infectious disorder3MONDO:0024355MONDO:0024355
post-traumatic stress disorder2MONDO:0005146EFO:0001358
acute lung injury2MONDO:0015796EFO:0004610
toxic shock syndrome2MONDO:0001881EFO:0006834
bronchiolitis2MONDO:0002465HP:0011950
hypertensive disorder1MONDO:0005044EFO:0000537
neoplasm1MONDO:0005070EFO:0000616
orthostatic hypotension1MONDO:0005469EFO:0005252
stomatitis1MONDO:0004842EFO:0009688
postural orthostatic tachycardia syndrome1MONDO:0011479EFO:1000645
mucositis1MONDO:0020579EFO:1001898
ovarian cyst1MONDO:0003282HP:0000138
ocular hypertension1MONDO:0006875EFO:1001069
vascular disorder0MONDO:0005385EFO:0004264
obesity disorder0MONDO:0011122EFO:0001073

7 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 186.

Phase distribution

PhaseTrials
Not specified70
PHASE452
PHASE318
PHASE216
PHASE110
EARLY_PHASE19
PHASE2/PHASE37
PHASE1/PHASE24

Top trials by phase / activity

NCTPhaseStatusTitle
NCT02118467PHASE4RECRUITINGVasoactive Drugs in Intensive Care Unit
NCT02323399PHASE4RECRUITINGStudy to Determine the Pharmacokinetics and Pharmacodynamic Effects of Phenylephrine on BP Via IV
NCT04934748PHASE4ENROLLING_BY_INVITATIONThe GUARDIAN Trial - Vasopressor Sub-Study
NCT06802224PHASE4RECRUITINGThe Choice of Vasopressor to Prevent Postoperative Acute Kidney Injury After Major Non-Cardiac Surgery
NCT00199784PHASE4COMPLETEDHemodynamic Measurements During Cesarean Section With Spinal Anesthesia
NCT00781157PHASE4COMPLETEDPhenylephrine for Spinal Induced Hypotension
NCT00796328PHASE4TERMINATEDUp-Down Determination of the ED90 of Phenylephrine for Hypotension Prophylaxis in Cesarean Delivery
NCT00846651PHASE4COMPLETEDSpinal Anesthesia Induced Hypotension During Cesarean Section
NCT00996190PHASE4COMPLETEDBest Regimen for Phenylephrine Administration During Cesarean Section
NCT01243970PHASE4TERMINATEDEphedrine vs Phenylephrine - ECG Changes
NCT01332578PHASE4COMPLETEDA Comparison of Solid and Soluble Forms of Cold and Influenza Remedies
NCT01378325PHASE4COMPLETEDVariable Rate Phenylephrine Infusion for Prevention of Spinal-induced Hypotension for Cesarean Delivery
NCT01481740PHASE4COMPLETEDPreventing Hypotension in Parturients With an Elevated Body Mass Index (BMI)
NCT01509521PHASE4COMPLETEDThe Oxygenation of the Brain During Caesarean Section
NCT01794273PHASE4COMPLETEDCompared Efficacy and Tolerance of Two Vasopressors Used to Treat Preoperative Hypotension During Carotid Surgery
NCT02025426PHASE4TERMINATEDPhenylephrine Versus Ephedrine in Pre-eclampsia
NCT02062710PHASE4COMPLETEDAntitussive Effect of a Naturally Flavored Syrup Containing Diphenhydramine, Compared With Dextromethorphan and Placebo
NCT02177539PHASE4UNKNOWNA New More Efficient Cycloplegia Scheme
NCT02203630PHASE4TERMINATEDPhenylephrine Versus Norepinephrine for Septic Shock in Critically Ill Patients
NCT02354833PHASE4COMPLETEDPhenylephrine vs. Norepinephrine Infusion After Spinal Anesthesia for Cesarean Delivery
NCT02373137PHASE4UNKNOWNDescemet Endothelial Thickness Comparison Trial
NCT02376192PHASE4COMPLETEDMaternal Microcirculation & SDF Imaging
NCT02675868PHASE4COMPLETEDEffects of Vasopressors on Immune Response
NCT02713087PHASE4COMPLETEDVasopressor Effects in Anesthetized Patients
NCT02739399PHASE4COMPLETEDEffects of Phenylephrine on Cardiac Preload
NCT02748265PHASE4COMPLETEDNebulized Epoprostenol (FLOLAN) and Phenylephrine on One Lung Ventilation (OLV)
NCT02802683PHASE4COMPLETEDHemodynamic Impact of Hyperbaric Versus Isobaric for Spinal Anesthesia During Cesarean Delivery
NCT02854787PHASE4COMPLETEDIntravenous Bolus of Phenylephrine vs. Norepinephrine in Preventing Hypotension After Spinal Anesthesia
NCT02885168PHASE4COMPLETEDModulation of Vasoreactivity in Septic Shock: Impact of Recombinant Protein C
NCT02969239PHASE4UNKNOWNNorepinephrine and Phenylephrine for Maternal Cardiac Output During Spinal Anesthesia for Elective Cesarean Delivery
NCT02979405PHASE4COMPLETEDEffectiveness of Phenylefrine in Prevention of Hypotension During Spinal Anesthesia for Cesarean Delivery
NCT03163914PHASE4COMPLETEDEffect of Vasopressors on Spinal Anaesthesia Induced Hypotension
NCT03248791PHASE4UNKNOWNVasopressor Infusion in Cesarean Delivery
NCT03328533PHASE4COMPLETEDNorepinephrine Versus Phenylephrine Continuous Variable Infusion in Cesarean Delivery
NCT03638726PHASE4UNKNOWNSubconjunctival Atropine and Intracameral Epinephrine for Pupil Dilation in Phacoemulsification
NCT03767296PHASE4COMPLETEDInfluence of a Bolus Administration of Ephedrine and Phenylephrine on the Spinal Oxygen Saturation, Measured With NIRS.
NCT03846765PHASE4COMPLETEDInfluence of Continuous Administration of Phenylephrine Versus Dobutamine on Spinal Oxygen Saturation, Measured With Near-infrared Spectroscopy (NIRS).
NCT03849508PHASE4COMPLETEDPhenylephrine Versus Norepinephrine for Maintenance of Hemodynamic During Cesarean Section Under Spinal Anesthesia
NCT03864094PHASE4COMPLETEDHemodynamics During Induction of General Anesthesia After Prophylactic Ephedrine, Phenylephrine or Norepinephrine.
NCT03872570PHASE4UNKNOWNEffect of Phenylephrine Versus Norepinephrine on Venous Return

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 6 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

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.

571 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
DIHYDROERGOTAMINEChEMBL + PubChemPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
ALFUZOSINChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
AMLODIPINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
APRACLONIDINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
ARIPIPRAZOLEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
ASENAPINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
ATENOLOLChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
AZELASTINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
BREXPIPRAZOLEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
BRIMONIDINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
BUSPIRONEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
CARIPRAZINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
CISAPRIDEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
CLONIDINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
CLOZAPINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
DEXMEDETOMIDINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
DOPAMINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
DOXAZOSINChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
EBASTINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
EPINEPHRINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
FENOLDOPAMChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
HALOPERIDOLChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
INDACATEROLChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
INDORAMINChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
ISOPROTERENOLChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
LABETALOLChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
MOXISYLYTEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
NAFTOPIDILChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
NEFAZODONEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
NOREPINEPHRINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
OLANZAPINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
OXYMETAZOLINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
PHENTOLAMINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
PRAZOSINChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
QUETIAPINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
RISPERIDONEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
SERTINDOLEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
SILODOSINChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
TAMSULOSINChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
TEGASERODChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
TERAZOSINChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
TERFENADINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
TOLAZOLINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
VERAPAMILChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
VILAZODONEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
XYLOMETAZOLINEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
ZIPRASIDONEChEMBLPhase 4 (approved)ADRA1A, ADRA1B, ADRA1D
BUNAZOSINChEMBLPhase 3ADRA1A, ADRA1B, ADRA1D
IDAZOXANChEMBLPhase 3ADRA1A, ADRA1B, ADRA1D
LATREPIRDINEChEMBLPhase 3ADRA1A, ADRA1B, ADRA1D
MEDETOMIDINEChEMBLPhase 3ADRA1A, ADRA1B, ADRA1D
YOHIMBINEChEMBLPhase 3ADRA1A, ADRA1B, ADRA1D
ABANOQUILChEMBLPhase 2ADRA1A, ADRA1B, ADRA1D
CIRAZOLINEChEMBLPhase 2ADRA1A, ADRA1B, ADRA1D
DEXNIGULDIPINEChEMBLPhase 2ADRA1A, ADRA1B, ADRA1D
IPSAPIRONEChEMBLPhase 2ADRA1A, ADRA1B, ADRA1D
MAZAPERTINEChEMBLPhase 2ADRA1A, ADRA1B, ADRA1D
NIGULDIPINEChEMBLPhase 2ADRA1A, ADRA1B, ADRA1D
PIPEROXANChEMBLPhase 2ADRA1A, ADRA1B, ADRA1D
PIZOTYLINEChEMBLPhase 2ADRA1A, ADRA1B, ADRA1D

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot