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Compound Detail

CHEMBL1437

NOREPINEPHRINE
💊 Approved Drug
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💊 Approved Drug
NC[C@H](O)c1ccc(O)c(O)c1

Basic Information

ChEMBL ID CHEMBL1437
Name NOREPINEPHRINE
Phase Approved
Structure Type MOL
InChI Key SFLSHLFXELFNJZ-QMMMGPOBSA-N
Therapeutic ✓ Yes

Known Names

(-)-noradrenaline Levarterenol Nor adrenalin Noradrenaline Norepinefrina Norepinephrine NSC-757246 R-norepinephrine
34
Targets
119
Activities
4
Assay Types
0
PK Parameters
20
Publications
8
Known Names
19
Indications

Molecular Properties

169.2
MW (Da)
0.09
ALogP
4
HBA
4
HBD
86.7
PSA (Ų)
0.47
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1950
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product
USAN Year 1980

Extended Properties

Molecular Formula C8H11NO3
MW 169.18
Aromatic Rings 1
Heavy Atoms 12
NP-Likeness 1.19

Indications

Cardiovascular Diseases Heart Diseases Hepatorenal Syndrome Hernias, Diaphragmatic, Congenital Hypotension Sepsis Shock Shock, Septic Stroke Syndrome Acute Lung Injury Brain Injuries Cognitive Dysfunction Depressive Disorder Hypotension, Orthostatic Inflammation Radiodermatitis Ischemic Stroke Obesity

ATC Classification

C01CA03
norepinephrine
Level 1: CARDIOVASCULAR SYSTEM
Level 2: CARDIAC THERAPY

Activity Summary

Ki 59 meas. best 8.32
EC50 47 meas. best 8.92
IC50 10 meas. best 7.8
Kd 3 meas. best 5.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Adrenergic receptor alpha-1
CHEMBL1907610
EC50 8.92 6.125 1.2 4
Adrenergic receptor alpha-2
CHEMBL2093864
Ki 8.32 7.5978 4.8 9
Beta-3 adrenergic receptor
CHEMBL246
EC50 8.26 8.23 5.5 2
Unchecked
CHEMBL612545
EC50 8.18 6.4186 6.6 7
Alpha-1A adrenergic receptor
CHEMBL229
EC50 8.04 7.2467 9.1 3
Alpha-1D adrenergic receptor
CHEMBL326
EC50 7.92 7.92 12.0 1
Adrenergic receptor alpha
CHEMBL2094111
IC50 7.8 6.55 16.0 2
Alpha-1D adrenergic receptor
CHEMBL326
Ki 7.65 7.65 22.4 1
Beta-1 adrenergic receptor
CHEMBL5471
EC50 7.52 6.3267 30.0 3
Adrenergic receptor alpha-2
CHEMBL2095158
Ki 7.52 7.52 30.0 1
Adrenergic receptor alpha-2
CHEMBL2093864
IC50 7.48 6.8 33.0 2
Adrenergic receptor beta
CHEMBL2095166
EC50 7.28 7.28 52.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
EC50 7.21 7.0475 61.7 4
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 7.2 7.2 63.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 7.18 7.18 66.0 1
Alpha-2B adrenergic receptor
CHEMBL266
Ki 7.11 7.11 78.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
EC50 6.96 6.65 110.0 8
Beta-1 adrenergic receptor
CHEMBL3252
Ki 6.9 5.94 126.0 6
Adrenergic receptor alpha-2
CHEMBL2095158
EC50 6.78 6.78 166.0 1
Beta-2 adrenergic receptor
CHEMBL5414
EC50 6.67 5.595 213.0 2
Alpha-1B adrenergic receptor
CHEMBL3122
Ki 6.58 6.58 263.0 1
Alpha-1A adrenergic receptor
CHEMBL319
Ki 6.55 6.55 281.8 1
Adrenergic receptor alpha-1
CHEMBL1907610
Ki 6.41 5.9922 390.0 9
Beta-1 adrenergic receptor
CHEMBL5471
Ki 6.4 6.4 400.0 1
Alpha-1A adrenergic receptor
CHEMBL4892
Ki 6.35 6.35 446.7 1
Alpha-2C adrenergic receptor
CHEMBL1916
EC50 6.35 6.15 446.7 5
Alpha-2C adrenergic receptor
CHEMBL4826
Ki 6.19 6.19 650.0 1
Adrenergic receptor beta
CHEMBL2095166
IC50 6.0 6.0 1000.0 1
Alpha-1A adrenergic receptor
CHEMBL319
EC50 5.93 5.93 1174.9 1
D(2) dopamine receptor
CHEMBL217
Ki 5.89 5.89 1300.0 1
Alpha-1A adrenergic receptor
CHEMBL229
Ki 5.82 5.315 1500.0 2
Adrenergic receptor alpha-1
CHEMBL1907610
IC50 5.82 5.805 1500.0 2
Cavia porcellus
CHEMBL369
EC50 5.82 5.82 1500.0 1
Beta-3 adrenergic receptor
CHEMBL4031
EC50 5.8 4.9 1580.0 2
Adrenergic receptor alpha-1
CHEMBL2094251
Ki 5.58 5.58 2600.0 1
Adrenergic receptor beta
CHEMBL2094118
EC50 5.58 5.58 2600.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 5.48 5.48 3311.3 1
Beta-2 adrenergic receptor
CHEMBL210
Ki 5.48 4.745 3300.0 2
Unchecked
CHEMBL612545
Ki 5.48 5.41 3310.0 2
Beta-2 adrenergic receptor
CHEMBL210
Kd 5.4 5.4 3980.0 2
Beta-2 adrenergic receptor
CHEMBL3754
Ki 5.38 5.38 4200.0 1
Beta-2 adrenergic receptor
CHEMBL2289
Ki 5.3 4.9433 5000.0 3
Alpha-2A adrenergic receptor
CHEMBL4075
Ki 5.24 5.24 5800.0 1
Beta-2 adrenergic receptor
CHEMBL3373
Ki 5.22 5.22 6000.0 2
Alpha-1B adrenergic receptor
CHEMBL315
EC50 4.99 4.99 10232.9 1
Alpha-1B adrenergic receptor
CHEMBL232
Ki 4.69 4.69 20400.0 1
D(1A) dopamine receptor
CHEMBL2056
Kd 4.3 4.3 50000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Adrenergic receptor alpha-1 EC50 = 1.2 nM 8.92 Effective dose for contraction of rat aorta. 7562902
Adrenergic receptor alpha-2 Ki = 4.8 nM 8.32 Compound was evaluated for alpha adrenergic binding affinity towards Alpha-2 adr... 1313109
Adrenergic receptor alpha-2 Ki = 4.8 nM 8.32 Tested for binding affinity against alpha-2 adrenergic receptor in rat brain usi... 8230093
Beta-3 adrenergic receptor EC50 = 5.5 nM 8.26 Agonist activity at human adrenergic beta-3 receptor expressed in CHO cells asse... 18083578
Beta-3 adrenergic receptor EC50 = 6.3 nM 8.2 Agonist activity at human adrenergic beta3 receptor expressed in CHO cells asses... 18083578
Unchecked EC50 = 6.6 nM 8.18 Effective dose for contraction of rabbit aorta. 7562902
Alpha-1A adrenergic receptor EC50 = 9.1 nM 8.04 Agonist activity at human alpha1A-adrenergic receptor expressed in HEK293 cells ... 26125514
Alpha-1A adrenergic receptor EC50 = 9.1 nM 8.04 Agonist activity at recombinant human alpha1A adrenergic receptor expressed in H... 28355078
Alpha-1D adrenergic receptor EC50 = 12.02 nM 7.92 In vitro agonist potency towards Alpha-1D adrenergic receptor in rat aorta 8831777
Adrenergic receptor alpha IC50 = 16.0 nM 7.8 Binding affinity against Alpha adrenergic receptor using [3H]dihydroergocryptine... 7328588
Adrenergic receptor alpha-2 Ki = 17.0 nM 7.77 Displacement of [3H]clonidine from Alpha-2 adrenergic receptor of rat brain memb... 6296387
Adrenergic receptor alpha-2 Ki = 20.0 nM 7.7 Binding of [3H]clonidine to alpha-2-adrenergic receptor of rat cerebral cortical... 10780918
Alpha-1D adrenergic receptor Ki = 22.39 nM 7.65 Binding affinity towards rat clonal Alpha-1D adrenergic receptor 8831777
Adrenergic receptor alpha-2 Ki = 30.0 nM 7.52 Binding of [3H]clonidine to alpha-2-adrenergic receptor of rat cerebral cortical... 10780918
Adrenergic receptor alpha-2 Ki = 30.0 nM 7.52 Binding affinity against alpha 2-Adrenergic receptor in guinea pig cerebral cort... 2845082
Unchecked EC50 = 30.0 nM 7.52 Effective dose for inhibition of neurotransmission in field-stimulated, reserpin... 7562902
Beta-1 adrenergic receptor EC50 = 30.0 nM 7.52 Effective concentration for Beta-1 adrenergic receptor mediated inhibition of ne... 7562902
Adrenergic receptor alpha-2 IC50 = 33.0 nM 7.48 The compound was evaluated for the inhibition of [3H]rauwolscine binding to alph... 2870187
Adrenergic receptor alpha-2 Ki = 37.0 nM 7.43 Binding affinity for alpha-2 adrenergic receptor in rat cortex using [3H]rauwols... 2884313
Adrenergic receptor alpha-2 Ki = 37.0 nM 7.43 The compound was evaluated for the binding affinity towards alpha-2 adrenergic r... 2870187

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 482
19857969 10.1016/j.bmc.2009.10.015 Beta-2 adrenergic receptor 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
2066997 10.1021/jm00111a047 Oryctolagus cuniculus 14
20052971 10.1021/np900608d 3T3-L1 8
191614 10.1021/jm00214a028 Unchecked 6
2982020 10.1021/jm00380a017 Alpha-1A adrenergic receptor 6
7562902 10.1021/jm00019a001 Unchecked 6
8831777 10.1021/jm960354u Alpha-1A adrenergic receptor 6
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 5
10476872 10.1016/s0960-894x(99)00395-9 ADMET 5
16407989 10.1038/nchembio705 Alpha-2A adrenergic receptor 5
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
3009812 10.1021/jm00155a025 Adrenergic receptor alpha 4
3009812 10.1021/jm00155a025 Adrenergic receptor beta 4
7562902 10.1021/jm00019a001 Adrenergic receptor alpha-1 4
10447956 10.1021/jm991004l Rattus norvegicus 4
16799554 10.1038/nchembio801 Unchecked 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
8632409 10.1021/jm950447w D(1A) dopamine receptor 3

Data from ChEMBL 36 via Core Engine