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

CHEMBL61006

PHENYLPROPANOLAMINE
💊 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
CC(N)C(O)c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL61006
Name PHENYLPROPANOLAMINE
Phase Approved
Structure Type MOL
InChI Key DLNKOYKMWOXYQA-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Fansia Fenilpropanolamina Norephedrine NSC-9920 Phenylfenesin Phenylpropanolamine Propadrine Rinexin
5
Targets
11
Activities
2
Assay Types
0
PK Parameters
20
Publications
8
Known Names
1
Indications

Molecular Properties

151.2
MW (Da)
1.07
ALogP
2
HBA
2
HBD
46.2
PSA (Ų)
0.66
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1958
Availability Withdrawn
Chirality Racemic

Routes of Administration

Oral

Flags

Withdrawn Natural Product
USAN Year 1987

Extended Properties

Molecular Formula C9H13NO
MW 151.21
Aromatic Rings 1
Heavy Atoms 11
NP-Likeness 0.57

Indications

Nasal Obstruction

ATC Classification

R01BA01
phenylpropanolamine
Level 1: RESPIRATORY SYSTEM
Level 2: NASAL PREPARATIONS
R01BA51
phenylpropanolamine, combinations
Level 1: RESPIRATORY SYSTEM
Level 2: NASAL PREPARATIONS

Drug Warnings

Withdrawn
neurotoxicity
risk of serious haemorrhagic strokes
Country: Australia; Bhutan; Timor-Leste; South Korea; United States; Canada; Singapore; Malaysia; Brazil; Germany   Year: 1987
Withdrawn
neurotoxicity
Haemorrhagic stroke. Severe high blood pressure.
Country: Australia; Bhutan; Timor-Leste; South Korea; United States; Canada; Singapore; Malaysia; Brazil; Germany   Year: 1987
Withdrawn
vascular toxicity
Haemorrhagic stroke. Severe high blood pressure.
Country: Australia; Bhutan; Timor-Leste; South Korea; United States; Canada; Singapore; Malaysia; Brazil; Germany   Year: 1987
Withdrawn
cardiotoxicity
Associated with strokes.
Country: Australia; Bhutan; Timor-Leste; South Korea; United States; Canada; Singapore; Malaysia; Brazil; Germany   Year: 1987
Withdrawn
neurotoxicity
Associated with strokes.
Country: Australia; Bhutan; Timor-Leste; South Korea; United States; Canada; Singapore; Malaysia; Brazil; Germany   Year: 1987
Withdrawn
neurotoxicity
Risk of hemorrhagic stroke
Country: Australia; Bhutan; Timor-Leste; South Korea; United States; Canada; Singapore; Malaysia; Brazil; Germany   Year: 1987
Withdrawn
vascular toxicity
hypertensive episodes in susceptible individuals, particularly when taken together with coffee, alcohol, antihistamines or neuroleptics
Country: Australia; Bhutan; Timor-Leste; South Korea; United States; Canada; Singapore; Malaysia; Brazil; Germany   Year: 1987
Withdrawn
neurotoxicity
Risk of haemorrhagic stroke
Country: Australia; Bhutan; Timor-Leste; South Korea; United States; Canada; Singapore; Malaysia; Brazil; Germany   Year: 1987
Withdrawn
neurotoxicity
potential of these products to induce several adverse reactions including cerebral haemorrhage
Country: Australia; Bhutan; Timor-Leste; South Korea; United States; Canada; Singapore; Malaysia; Brazil; Germany   Year: 1987
Withdrawn
vascular toxicity
hypertensive episodes in susceptible individuals, particularly when taken together with coffee, alcohol, antihistamines or neuroleptics
Country: Australia; Bhutan; Timor-Leste; South Korea; United States; Canada; Singapore; Malaysia; Brazil; Germany   Year: 1987

Activity Summary

Ki 8 meas. best 6.58
EC50 3 meas. best 4.12

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Alpha-2B adrenergic receptor
CHEMBL266
 Ki 6.58 6.58 263.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
 Ki 6.56 6.56 275.4 1
Alpha-1D adrenergic receptor
CHEMBL326
 Ki 5.07 5.07 8511.4 2
Alpha-1B adrenergic receptor
CHEMBL3122
 Ki 5.02 5.02 9549.9 2
Alpha-1A adrenergic receptor
CHEMBL319
 Ki 5.01 5.01 9772.4 2
Alpha-1D adrenergic receptor
CHEMBL326
 EC50 4.12 4.12 75857.8 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Alpha-2B adrenergic receptor Ki = 263.03 nM 6.58 In vitro binding affinity towards alpha-2B adrenergic receptor of rat neonatal l... 15163201
Alpha-2A adrenergic receptor Ki = 275.42 nM 6.56 In vitro binding affinity towards alpha-2A adrenergic receptor of human clone in... 15163201
Alpha-1D adrenergic receptor Ki = 8511.38 nM 5.07 In vitro binding affinity towards alpha-1D adrenergic receptor of rat clone in r... 15163201
Alpha-1D adrenergic receptor Ki = 8511.38 nM 5.07 Binding affinity to Rattus norvegicus (rat) alpha1D adrenoreceptor by radioligan... -
Alpha-1B adrenergic receptor Ki = 9549.93 nM 5.02 In vitro binding affinity towards alpha-1B adrenergic receptor of hamster clone ... 15163201
Alpha-1B adrenergic receptor Ki = 9549.93 nM 5.02 Binding affinity to Cricetinae (hamster) alpha1B adrenoreceptor by radioligand d... -
Alpha-1A adrenergic receptor Ki = 9772.37 nM 5.01 In vitro binding affinity towards alpha-1A adrenergic receptor of rat submaxilla... 15163201
Alpha-1A adrenergic receptor Ki = 9772.37 nM 5.01 Binding affinity to alpha1A adrenoreceptor in Rattus norvegicus (rat) submaxilla... -
Alpha-1D adrenergic receptor EC50 = 75857.76 nM 4.12 Agonist activity at alpha1D adrenoreceptor in Rattus norvegicus (rat) aorta -

Literature References

PubMed DOI Target Context # Activities
15163201 10.1021/jm030551a Unchecked 5
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
15163201 10.1021/jm030551a Alpha-1B adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 2B 3
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 3
37468498 10.1038/s41467-023-40064-9 5-hydroxytryptamine receptor 1A 3
- 10.1007/s00044-004-0020-z Alpha-1A adrenergic receptor 3
- 10.1007/s00044-004-0020-z Alpha-1B adrenergic receptor 3
- 10.1007/s00044-004-0020-z Alpha-1D adrenergic receptor 3
15163201 10.1021/jm030551a Canis familiaris 3
15163201 10.1021/jm030551a Alpha-2A adrenergic receptor 3
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
15163201 10.1021/jm030551a Alpha-1D adrenergic receptor 3
15163201 10.1021/jm030551a Alpha-1A adrenergic receptor 3
1246042 10.1021/jm00223a036 Vas deferens 2
37468498 10.1038/s41467-023-40064-9 Histamine H2 receptor 2
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 2
37468498 10.1038/s41467-023-40064-9 Gamma-aminobutyric acid receptor subunit alpha-1 2
37468498 10.1038/s41467-023-40064-9 Beta-2 adrenergic receptor 2

Data from ChEMBL 36 via Core Engine