Compound Detail

CHEMBL679

EPINEPHRINE

💊 Approved Drug

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💊 Approved Drug

CNC[C@H](O)c1ccc(O)c(O)c1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL679
Name	EPINEPHRINE
Phase	Approved
Structure Type	MOL
InChI Key	UCTWMZQNUQWSLP-VIFPVBQESA-N
Therapeutic	✓ Yes

Known Names

(-)-(r)-epinephrine (-)-epinephrine Adren co Adrenaclick Adrenalin Adrenaline Adrenalinum Ana-guard Ana-kit Anapen Anaphylactic shock drug kit Asma-vydrin +18 more

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

183.2

MW (Da)

0.35

ALogP

HBA

HBD

72.7

PSA (Å²)

0.51

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1965
Availability	OTC
Chirality	Single Enantiomer

Routes of Administration

Parenteral Topical

Flags

Natural Product

Extended Properties

Molecular Formula	C9H13NO3
MW	183.21
Aromatic Rings	1
Heavy Atoms	13
NP-Likeness	1.12

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Adrenergic receptor agonist	AGONIST	Adrenergic receptor	✓	✓

Indications

Angioedema Asthma Bronchial Spasm Cardiovascular Diseases Glaucoma Heart Arrest Heart Arrest Hemorrhage Hypersensitivity Lung Diseases, Obstructive Muscle Cramp Mydriasis Nasal Obstruction Rhinitis, Allergic, Seasonal Rhinitis, Allergic, Seasonal Serum Sickness Shock, Septic Sinusitis Urticaria Bronchiolitis

ATC Classification

A01AD01

epinephrine

Level 1: ALIMENTARY TRACT AND METABOLISM

Level 2: STOMATOLOGICAL PREPARATIONS

B02BC09

epinephrine

Level 1: BLOOD AND BLOOD FORMING ORGANS

Level 2: ANTIHEMORRHAGICS

C01CA24

epinephrine

Level 1: CARDIOVASCULAR SYSTEM

Level 2: CARDIAC THERAPY

R01AA14

epinephrine

Level 1: RESPIRATORY SYSTEM

Level 2: NASAL PREPARATIONS

R03AA01

epinephrine

Level 1: RESPIRATORY SYSTEM

Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES

R03AK01

epinephrine and other drugs for obstructive airway diseases

Level 1: RESPIRATORY SYSTEM

Level 2: DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES

S01EA01

epinephrine

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICALS

S01EA51

epinephrine, combinations

Level 1: SENSORY ORGANS

Level 2: OPHTHALMOLOGICALS

Activity Summary

Ki 35 meas. best 8.3

EC50 18 meas. best 8.25

IC50 12 meas. best 8.1

Kd 3 meas. best 6.2

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Adrenergic receptor alpha-2 CHEMBL2095158	Ki	8.3	8.3	5.0	1
Alpha-2A adrenergic receptor CHEMBL1867	EC50	8.25	7.885	5.6	2
Adrenergic receptor alpha-2 CHEMBL2095158	IC50	8.1	8.1	8.0	1
Adrenergic receptor alpha-2 CHEMBL2093864	Ki	7.89	7.4825	13.0	4
Beta-1 adrenergic receptor CHEMBL5471	EC50	7.82	6.92	15.0	3
Beta-2 adrenergic receptor CHEMBL5414	EC50	7.82	7.09	15.0	2
Adrenergic receptor alpha CHEMBL2094111	IC50	7.77	7.77	17.0	1
Beta-3 adrenergic receptor CHEMBL246	EC50	7.51	7.41	31.0	2
Alpha-1B adrenergic receptor CHEMBL232	EC50	7.12	7.12	75.0	1
Unchecked CHEMBL612545	Ki	7.0	6.9233	100.0	3
Alpha-2A adrenergic receptor CHEMBL1867	Ki	6.8	6.68	160.0	2
Beta-2 adrenergic receptor CHEMBL210	Ki	6.71	6.575	196.0	2
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	6.7	5.704	200.0	5
Alpha-1D adrenergic receptor CHEMBL223	Ki	6.66	6.66	221.0	1
Adrenergic receptor beta CHEMBL2095166	EC50	6.64	6.64	230.0	2
Unchecked CHEMBL612545	IC50	6.63	6.63	232.0	1
Alpha-1A adrenergic receptor CHEMBL319	Ki	6.59	6.59	254.0	1
Beta-2 adrenergic receptor CHEMBL210	IC50	6.55	6.55	284.0	1
Beta-1 adrenergic receptor CHEMBL213	EC50	6.54	6.54	290.0	1
Adrenergic receptor alpha-2 CHEMBL2095158	EC50	6.52	6.52	300.0	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	6.45	6.195	356.0	2
Alpha-1A adrenergic receptor CHEMBL229	EC50	6.4	6.4	400.0	1
Cavia porcellus CHEMBL369	EC50	6.4	6.4	400.0	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	6.4	6.08	397.0	2
Alpha-1D adrenergic receptor CHEMBL223	IC50	6.35	6.35	449.0	1
Beta-2 adrenergic receptor CHEMBL210	EC50	6.21	6.21	615.5	1
Beta-2 adrenergic receptor CHEMBL210	Kd	6.2	6.2	630.0	2
Alpha-1A adrenergic receptor CHEMBL319	IC50	6.2	6.2	628.0	1
Beta-2 adrenergic receptor CHEMBL2289	Ki	6.18	6.07	660.0	2
Beta-2 adrenergic receptor CHEMBL3754	Ki	6.14	6.14	720.0	1
Alpha-2A adrenergic receptor CHEMBL1867	IC50	6.13	6.13	737.0	1
Alpha-2B adrenergic receptor CHEMBL1942	IC50	6.06	6.06	869.0	1
D(2) dopamine receptor CHEMBL217	Ki	6.04	6.04	910.0	1
Alpha-1B adrenergic receptor CHEMBL315	Ki	6.01	6.01	977.0	1
Beta-1 adrenergic receptor CHEMBL3252	Ki	5.96	5.8533	1100.0	3
Alpha-1B adrenergic receptor CHEMBL315	IC50	5.75	5.75	1766.0	1
Alpha-1A adrenergic receptor CHEMBL229	Ki	5.7	5.7	2000.0	1
Alpha-2C adrenergic receptor CHEMBL1916	IC50	5.61	5.61	2449.0	1
Beta-1 adrenergic receptor CHEMBL5471	Ki	5.52	5.52	3000.0	1
Polyunsaturated fatty acid lipoxygenase ALOX15 CHEMBL4358	IC50	5.48	5.48	3279.0	1
Adrenergic receptor alpha-1 CHEMBL1907610	EC50	5.39	5.39	4073.0	1
Adrenergic receptor beta CHEMBL2095166	IC50	4.54	4.54	29000.0	1
D(1A) dopamine receptor CHEMBL2056	Kd	4.26	4.26	55000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
F	20.0	%	Homo sapiens
Ka	0.09	uM	Homo sapiens
Ka	96.0	uM	Homo sapiens
Ka	45.0	uM	Homo sapiens
Ka	63.0	uM	Homo sapiens
Ka	60.0	uM	Homo sapiens
Ka	36.0	uM	Homo sapiens
KA	0.72	uM	Malassezia globosa
KA	0.09	uM	Homo sapiens
KA	96.0	uM	Homo sapiens
KA	39.0	uM	Methanosarcina thermophila
KA	0.019	uM	Burkholderia pseudomallei
KA	0.09	uM	Homo sapiens
KA	96.0	uM	Homo sapiens
KA	4.89	uM	Leishmania chagasi
KA	100.0	uM	Trypanosoma cruzi
KA	0.09	uM	Homo sapiens
KA	96.0	uM	Homo sapiens
KA	45.0	uM	Homo sapiens
KA	63.0	uM	Homo sapiens
KA	60.0	uM	Homo sapiens
KA	36.0	uM	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Adrenergic receptor alpha-2	Ki	=	5.0	nM	8.3	Binding affinity against alpha 2-Adrenergic receptor in guinea pig cerebral cort...	2845082
Alpha-2A adrenergic receptor	EC50	=	5.626	nM	8.25	GPCR PRESTO-Tango dose-response in agonist mode with target: ADRA2A	-
Adrenergic receptor alpha-2	IC50	=	8.0	nM	8.1	Inhibition of [3H]p-aminoclonidine (PAC) binding to alpha-2 adrenergic receptor ...	3037080
Adrenergic receptor alpha-2	Ki	=	13.0	nM	7.89	Binding of [3H]clonidine to alpha-2-adrenergic receptor of rat cerebral cortical...	10780918
Adrenergic receptor alpha-2	Ki	=	15.0	nM	7.82	Binding of [3H]clonidine to alpha-2-adrenergic receptor of rat cerebral cortical...	10780918
Beta-1 adrenergic receptor	EC50	=	15.0	nM	7.82	Effective dose required to stimulate contractions in isolated guinea pig atrium.	7562902
Beta-2 adrenergic receptor	EC50	=	15.0	nM	7.82	Effective dose for relaxation of guinea pig trachea.	7562902
Adrenergic receptor alpha	IC50	=	17.0	nM	7.77	Binding affinity against Alpha adrenergic receptor using [3H]dihydroergocryptine...	7328588
Alpha-2A adrenergic receptor	EC50	=	30.2	nM	7.52	Agonist activity at recombinant human alpha2A adrenoreceptor expressed in CHOK1 ...	27265687
Beta-3 adrenergic receptor	EC50	=	31.0	nM	7.51	Agonist activity at human adrenergic beta-3 receptor expressed in CHO cells asse...	18083578
Adrenergic receptor alpha-2	Ki	=	38.0	nM	7.42	Displacement of [3H]clonidine from adrenergic alpha 2 receptor of rat cerebral c...	8254623
Beta-3 adrenergic receptor	EC50	=	49.0	nM	7.31	Agonist activity at human adrenergic beta3 receptor expressed in CHO cells asses...	18083578
Alpha-1B adrenergic receptor	EC50	=	75.0	nM	7.12	Agonist activity at human alpha1 beta adrenergic receptor expressed in CHOK1 cel...	31625751
Unchecked	Ki	=	100.0	nM	7.0	Binding affinity to human beta-2 adrenergic receptor delta 5-C271/W135 mutant ex...	16799554
Unchecked	Ki	=	110.0	nM	6.96	Binding affinity to human beta-2 adrenergic receptor delta 5-C271 mutant express...	16799554
Unchecked	Ki	=	154.0	nM	6.81	DRUGMATRIX: Imidazoline I2, Central radioligand binding (ligand: [3H] Idazoxan)	-
Alpha-2A adrenergic receptor	Ki	=	160.0	nM	6.8	Displacement of [3H]RS-79948-197 from recombinant human alpha2A adrenoreceptor e...	27265687
Adrenergic receptor alpha-2	Ki	=	160.0	nM	6.8	Displacement of radioligand from rat alpha2 adrenergic receptor by liquid scinti...	9182127
Beta-2 adrenergic receptor	Ki	=	196.0	nM	6.71	DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177)	-
Adrenergic receptor alpha-1	Ki	=	200.0	nM	6.7	Compound was evaluated for inhibition of [3H]prazosin binding to Alpha-1 adrener...	7328589

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	523
-	10.6019/CHEMBL5058577	U2OS	304
-	10.6019/CHEMBL5058577	HEK-293T	304
-	10.6019/CHEMBL5724801	Fibroblast	304
-	10.6019/CHEMBL5724801	U2OS	304
-	10.6019/CHEMBL5058577	Fibroblast	304
-	10.6019/CHEMBL5724801	HEK-293T	304
17646643	10.1073/pnas.0705611104	Mus musculus	15
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
-	10.6019/CHEMBL5058564	U2OS	9
10476872	10.1016/s0960-894x(99)00395-9	ADMET	5
10447956	10.1021/jm991004l	Rattus norvegicus	4
-	10.6019/CHEMBL5058564	HEK-293T	4
16799554	10.1038/nchembio801	Unchecked	4
6319700	10.1021/jm00368a014	Felis catus	4
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	3
2836587	10.1021/jm00401a004	Beta-2 adrenergic receptor	3
671451	10.1021/jm00204a009	Rattus norvegicus	3
8632409	10.1021/jm950447w	D(1A) dopamine receptor	3
37468498	10.1038/s41467-023-40064-9	Alpha-2A adrenergic receptor	3

Data from ChEMBL 36 via Core Engine