Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL1215

PHENYLEPHRINE
💊 Approved Drug
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
💊 Approved Drug
CNC[C@H](O)c1cccc(O)c1

Basic Information

ChEMBL ID CHEMBL1215
Name PHENYLEPHRINE
Phase Approved
Structure Type MOL
InChI Key SONNWYBIRXJNDC-VIFPVBQESA-N
Therapeutic ✓ Yes

Known Names

(-)-phenylephrine (r)-phenylephrine AB-101 (PHENYLEPHRINE) Cyclomydril Duo-medihaler Fenilefrina J8.601K M-oxedrine M-sympathol M-sympatol M-synephrine Meta-synephrine +5 more
19
Targets
34
Activities
3
Assay Types
3
PK Parameters
20
Publications
17
Known Names
20
Indications

Molecular Properties

167.2
MW (Da)
0.65
ALogP
3
HBA
3
HBD
52.5
PSA (Ų)
0.62
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1952
Availability OTC
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral Topical

Flags

Natural Product

Extended Properties

Molecular Formula C9H13NO2
MW 167.21
Aromatic Rings 1
Heavy Atoms 12
NP-Likeness 0.74

Indications

Cardiovascular Diseases Eye Manifestations Hemorrhoids Nasal Obstruction Common Cold Eye Diseases Fecal Incontinence Hypotension Influenza, Human Ischemic Stroke Respiratory Tract Infections Rhinitis, Allergic, Seasonal Stroke Acute Lung Injury Bronchiolitis Cognitive Dysfunction Mydriasis Shock, Septic Stress Disorders, Post-Traumatic Hypertension

ATC Classification

C01CA06
phenylephrine
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CARDIAC THERAPY
C05AX06
phenylephrine
Level 1: CARDIOVASCULAR SYSTEM
Level 2: VASOPROTECTIVES
R01AA04
phenylephrine
Level 1: RESPIRATORY SYSTEM
Level 2: NASAL PREPARATIONS
R01AB01
phenylephrine
Level 1: RESPIRATORY SYSTEM
Level 2: NASAL PREPARATIONS
R01BA03
phenylephrine
Level 1: RESPIRATORY SYSTEM
Level 2: NASAL PREPARATIONS
R01BA53
phenylephrine, combinations
Level 1: RESPIRATORY SYSTEM
Level 2: NASAL PREPARATIONS
S01FB01
phenylephrine
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
S01GA05
phenylephrine
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS
S01GA55
phenylephrine, combinations
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

EC50 17 meas. best 9.07
Ki 14 meas. best 6.79
IC50 3 meas. best 7.11

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Alpha-1B adrenergic receptor
CHEMBL232
EC50 9.07 8.65 0.9 2
Alpha-1A adrenergic receptor
CHEMBL4892
EC50 8.05 8.05 9.0 1
Alpha-1B adrenergic receptor
CHEMBL3988626
EC50 8.0 8.0 10.0 1
Alpha-1A adrenergic receptor
CHEMBL229
EC50 7.26 6.68 55.0 3
Adrenergic receptor alpha-2
CHEMBL2093864
IC50 7.11 6.695 78.0 2
Alpha-1D adrenergic receptor
CHEMBL326
EC50 6.81 6.81 154.9 1
Alpha-1D adrenergic receptor
CHEMBL326
Ki 6.79 6.79 162.2 1
Adrenergic receptor alpha-2
CHEMBL2093864
Ki 6.57 6.49 270.0 2
Alpha-2A adrenergic receptor
CHEMBL1867
EC50 6.51 6.415 306.0 2
Alpha-2C adrenergic receptor
CHEMBL1916
EC50 6.47 6.47 340.0 1
Adrenergic receptor alpha-2
CHEMBL2095158
Ki 6.41 6.41 390.0 1
Alpha-1A adrenergic receptor
CHEMBL4892
Ki 6.03 6.03 933.2 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 6.01 6.01 977.2 1
5-hydroxytryptamine receptor 7
CHEMBL3155
Ki 5.96 5.96 1110.1 1
Alpha-1B adrenergic receptor
CHEMBL3122
Ki 5.9 5.9 1258.9 1
Alpha-1A adrenergic receptor
CHEMBL319
EC50 5.78 5.78 1659.6 1
Adrenergic receptor alpha-1
CHEMBL1907610
IC50 5.7 5.7 2000.0 1
Unchecked
CHEMBL612545
Ki 5.6 5.405 2500.0 2
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 5.49 5.49 3216.6 1
Cavia porcellus
CHEMBL369
EC50 5.22 4.79 6000.0 3
Adrenergic receptor beta
CHEMBL2094118
EC50 5.22 5.22 6000.0 1
Adrenergic receptor alpha-1
CHEMBL1907610
Ki 5.21 5.21 6100.0 1
Alpha-1B adrenergic receptor
CHEMBL315
EC50 4.96 4.96 10964.8 1
Beta-1 adrenergic receptor
CHEMBL3252
Ki 4.89 4.89 13000.0 1
Adrenergic receptor beta; ADRB1 & ADRB3
CHEMBL2097169
Ki 4.89 4.89 13000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 30.0 mL.min-1.kg-1 Homo sapiens
CL 17.3 mL.min-1.g-1 Homo sapiens
F 49.0 % Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Alpha-1B adrenergic receptor EC50 = 0.86 nM 9.07 Intrinsic activity at human alpha1B adrenergic receptor expressed in CHOK1 cells... 27658792
Alpha-1B adrenergic receptor EC50 = 5.9 nM 8.23 Agonist activity at alpha-1B adrenergic receptor (unknown origin) after 5 hrs by... 25813897
Alpha-1A adrenergic receptor EC50 = 9.0 nM 8.05 Agonist activity at bovine recombinant alpha-1A receptor expressed in HEK293 cel... -
Alpha-1B adrenergic receptor EC50 = 10.0 nM 8.0 Agonist activity at hamster recombinant alpha-1B receptor expressed in HEK293 ce... -
Alpha-1A adrenergic receptor EC50 = 55.0 nM 7.26 Agonist activity at alpha-1A adrenergic receptor (unknown origin) after 5 hrs by... 25813897
Alpha-1A adrenergic receptor EC50 = 55.99 nM 7.25 Intrinsic activity at alpha1A adrenergic receptor (unknown origin) after 5 hrs i... 27658792
Adrenergic receptor alpha-2 IC50 = 78.0 nM 7.11 Inhibitory activity against Alpha-2 adrenergic receptor in rat vas deferens 2567783
Alpha-1D adrenergic receptor EC50 = 154.88 nM 6.81 In vitro agonist potency towards Alpha-1D adrenergic receptor in rat aorta 8831777
Alpha-1D adrenergic receptor Ki = 162.18 nM 6.79 Binding affinity towards rat clonal Alpha-1D adrenergic receptor 8831777
Adrenergic receptor alpha-2 Ki = 270.0 nM 6.57 Displacement of [3H]clonidine from Alpha-2 adrenergic receptor of rat brain memb... 6296387
Alpha-2A adrenergic receptor EC50 = 306.0 nM 6.51 Agonist activity at human recombinant alpha-2A receptor expressed in PC12 cells ... -
Alpha-2C adrenergic receptor EC50 = 340.0 nM 6.47 Agonist activity at human recombinant alpha-2C receptor expressed in PC12 cells ... -
Adrenergic receptor alpha-2 Ki = 390.0 nM 6.41 Compound was tested for its ability to displace [3H]clonidine form alpha-2 adren... 3020250
Adrenergic receptor alpha-2 Ki = 390.0 nM 6.41 Displacement of [3H]clonidine from adrenergic alpha 2 receptor of rat cerebral c... 8254623
Alpha-2A adrenergic receptor EC50 = 476.65 nM 6.32 GPCR PRESTO-Tango dose-response in agonist mode with target: ADRA2A -
Adrenergic receptor alpha-2 IC50 = 520.0 nM 6.28 50% inhibition of specific [3H]clonidine binding (0.4 nM) to Alpha-2 adrenergic ... 6142954
Alpha-1A adrenergic receptor Ki = 933.25 nM 6.03 Binding affinity towards bovine clonal Alpha-1A adrenergic receptor 8831777
Alpha-1A adrenergic receptor Ki = 977.24 nM 6.01 Binding affinity towards Alpha-1A adrenergic receptor in rat submaxillary glands 8831777
5-hydroxytryptamine receptor 7 Ki = 1110.07 nM 5.96 PDSP Secondary Binding target: HTR7 - Compounds are tested at 10 uM concentratio... -
Alpha-1B adrenergic receptor Ki = 1258.93 nM 5.9 Binding affinity towards hamster clonal Alpha-1B adrenergic receptor 8831777

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 482
- 10.6019/CHEMBL4689842 HEK-293T 10
- 10.6019/CHEMBL4689842 U2OS 8
8831777 10.1021/jm960354u Alpha-1A adrenergic receptor 6
2982020 10.1021/jm00380a017 Alpha-1A adrenergic receptor 6
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 5
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 5
- 10.6019/CHEMBL5209801 Adhesion G-protein coupled receptor F1 5
- 10.6019/CHEMBL5209801 Glucagon-like peptide 1 receptor 5
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 5
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 5
- 10.6019/CHEMBL5209801 Alpha-2A adrenergic receptor 5
- 10.6019/CHEMBL5209801 Apelin receptor 5
- 10.6019/CHEMBL4689842 Fibroblast 5
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 5
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 5
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 5
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 5
- 10.6019/CHEMBL5209801 Sphingosine 1-phosphate receptor 1 5
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 4

Data from ChEMBL 36 via Core Engine