Compound Detail

CHEMBL53

APOMORPHINE

💊 Approved Drug

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💊 Approved Drug

CN1CCc2cccc3c2[C@H]1Cc1ccc(O)c(O)c1-3

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL53
Name	APOMORPHINE
Phase	Approved
Structure Type	MOL
InChI Key	VMWNQDUVQKEIOC-CYBMUJFWSA-N
Therapeutic	✓ Yes

Known Names

6a.beta.-aporphine-10,11-diol APL-130277 Apomorphine Apomorphinum VR-040 VR040

Targets

211

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

267.3

MW (Da)

2.85

ALogP

HBA

HBD

43.7

PSA (Å²)

0.72

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	2001
Availability	Prescription
Chirality	Single Enantiomer

Routes of Administration

Parenteral Topical

Flags

Natural Product

Extended Properties

Molecular Formula	C17H17NO2
MW	267.33
Aromatic Rings	2
Heavy Atoms	20
NP-Likeness	1.45

Indications

Erectile Dysfunction Parkinson Disease Alcoholism Brain Injuries Hallucinations

ATC Classification

G04BE07

apomorphine

Level 1: GENITO URINARY SYSTEM AND SEX HORMONES

Level 2: UROLOGICALS

N04BC07

apomorphine

Level 1: NERVOUS SYSTEM

Level 2: ANTI-PARKINSON DRUGS

Activity Summary

Ki 83 meas. best 9.21

IC50 80 meas. best 9.0

EC50 40 meas. best 9.4

Kd 8 meas. best 9.18

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
D(2) dopamine receptor CHEMBL339	EC50	9.4	8.468	0.4	5
D(2) dopamine receptor CHEMBL217	Ki	9.21	7.4735	0.6	20
D(2) dopamine receptor CHEMBL217	Kd	9.18	7.9	0.7	3
D(2) dopamine receptor CHEMBL339	IC50	9.0	7.7174	1.0	19
Dopamine receptor CHEMBL2096970	IC50	9.0	7.2569	1.0	13
Dopamine receptor CHEMBL2093868	IC50	9.0	7.988	1.0	10
Unchecked CHEMBL612545	EC50	8.82	8.82	1.5	1
D(4) dopamine receptor CHEMBL3361	EC50	8.82	8.4467	1.5	3
D(2) dopamine receptor CHEMBL217	EC50	8.8	8.1708	1.6	13
Dopamine receptors; D1 & D2 CHEMBL2096910	IC50	8.77	8.77	1.7	1
D(2) dopamine receptor CHEMBL339	Ki	8.74	7.8985	1.8	13
D(3) dopamine receptor CHEMBL234	Ki	8.59	8.01	2.6	5
Dopamine receptor CHEMBL2096970	Ki	8.43	8.43	3.7	1
D(1A) dopamine receptor CHEMBL2056	EC50	8.42	7.3783	3.8	6
D(2) dopamine receptor CHEMBL217	IC50	8.38	7.655	4.2	2
D(4) dopamine receptor CHEMBL219	EC50	8.37	8.37	4.3	2
D(4) dopamine receptor CHEMBL219	Ki	8.36	8.205	4.4	2
D(1A) dopamine receptor CHEMBL2056	Ki	8.34	6.7322	4.6	9
D(3) dopamine receptor CHEMBL234	EC50	8.15	8.15	7.0	1
Rattus norvegicus CHEMBL376	Ki	7.98	7.98	10.5	1
D(1B) dopamine receptor CHEMBL1850	Ki	7.82	7.27	15.0	2
Rattus norvegicus CHEMBL376	IC50	7.65	6.9233	22.6	3
Dopamine receptor D2 and D3 CHEMBL2111342	IC50	7.61	7.385	24.3	2
Dopamine receptor CHEMBL2096905	IC50	7.6	7.6	25.0	1
D(3) dopamine receptor CHEMBL3138	IC50	7.57	7.55	27.2	2
Alpha-2C adrenergic receptor CHEMBL1916	Ki	7.44	7.44	36.3	1
Oryctolagus cuniculus CHEMBL374	EC50	7.36	7.36	44.0	1
D(1A) dopamine receptor CHEMBL265	Ki	7.28	6.5856	53.0	9
Adrenergic receptor alpha-2 CHEMBL2093864	IC50	7.2	6.6467	63.0	3
Alpha-1D adrenergic receptor CHEMBL223	Ki	7.19	7.19	64.6	1
Alpha-2B adrenergic receptor CHEMBL1942	Ki	7.18	7.18	66.1	1
D(1A) dopamine receptor CHEMBL3071	Ki	7.0	7.0	101.0	1
5-hydroxytryptamine receptor 2C CHEMBL225	Ki	6.99	6.99	102.0	1
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	6.93	6.558	117.0	5
5-hydroxytryptamine receptor 2A CHEMBL224	Ki	6.92	6.92	120.0	2
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	6.88	6.88	132.0	1
NON-PROTEIN TARGET CHEMBL3879801	EC50	6.78	5.8614	168.0	7
5-hydroxytryptamine receptor 7 CHEMBL3223	Ki	6.73	6.73	188.0	3
E3 ubiquitin-protein ligase Mdm2 CHEMBL5023	IC50	6.71	6.69	195.0	2
D(2) dopamine receptor CHEMBL339	Kd	6.7	6.16	200.0	4
D(2) dopamine receptor CHEMBL3998	Ki	6.7	6.7	200.0	1
D(1A) dopamine receptor CHEMBL265	IC50	6.62	6.3233	238.0	9
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	6.53	6.53	296.0	3
Opioid receptor CHEMBL2094129	IC50	6.52	6.52	302.0	1
Unchecked CHEMBL612545	Ki	6.27	6.27	532.0	1
Unchecked CHEMBL612545	IC50	6.22	5.515	600.0	2
D(1A) dopamine receptor CHEMBL2056	Kd	6.17	6.17	680.0	1
Voltage-gated inwardly rectifying potassium channel KCNH2 CHEMBL240	IC50	5.62	5.62	2398.8	1
Zinc finger protein mex-5 CHEMBL1293319	EC50	5.48	5.48	3293.0	1
Aspartyl aminopeptidase CHEMBL1293263	IC50	5.43	5.43	3669.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	40.0	mL.min-1.kg-1	Homo sapiens
Fu	0.057	-	Homo sapiens
MRT	0.67	hr	Homo sapiens
T1/2	0.68	hr	Homo sapiens
T1/2	1.0	hr	Not specified

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
D(2) dopamine receptor	EC50	=	0.4	nM	9.4	Agonist activity at rat D2 receptor in HEK293 cells coexpressing G-alpha-qo5 by ...	17149874
D(2) dopamine receptor	EC50	=	0.4	nM	9.4	In vitro effective concentration tested on HEK293 cells co-transfected with rat ...	15239663
D(2) dopamine receptor	Ki	=	0.62	nM	9.21	Displacement of [3H]spiperone from human dopamine D2 receptor at high affinity s...	20155917
D(2) dopamine receptor	Kd	=	0.66	nM	9.18	Compound was evaluated for the ability to displace [3H]spiperone at Dopamine rec...	2524592
Dopamine receptor	IC50	=	1.0	nM	9.0	Tested for binding to dopamine receptor using [3H]apomorphine as radioligand in ...	7120288
Dopamine receptor	IC50	=	1.0	nM	9.0	Inhibition of [3H]apomorphine binding to calf caudate membrane preparation (p4)	7310821
D(2) dopamine receptor	IC50	=	1.0	nM	9.0	Evaluated for the affinity against Dopamine receptor D2 in rat striatal membrane...	2968456
Dopamine receptor	IC50	=	1.1	nM	8.96	Dopaminergic activity assessed in vitro for displacement of [3H]apomorphine from...	6094811
Dopamine receptor	IC50	=	1.4	nM	8.85	Inhibitory concentration for half-maximal displacement of 1.0 nM [3H]ADTN specif...	7200145
D(4) dopamine receptor	EC50	=	1.5	nM	8.82	In vitro effective concentration tested on HEK293 cells co-transfected with ferr...	15239663
Unchecked	EC50	=	1.5	nM	8.82	Agonist activity at ferret D4 receptor in HEK293 cells coexpressing G-alpha-qo5 ...	17149874
D(2) dopamine receptor	EC50	=	1.585	nM	8.8	Agonist activity at D2 long receptor (unknown origin) transfected in human HEK29...	32184974
D(2) dopamine receptor	EC50	=	1.61	nM	8.79	Agonist activity at D2 long receptor (unknown origin) transfected in human HEK29...	32184974
D(2) dopamine receptor	EC50	=	1.7	nM	8.77	Agonist activity at human recombinant dopamine D2L receptor expressed in CHOFlpI...	-
D(2) dopamine receptor	IC50	=	1.7	nM	8.77	Affinity of the Compound for Dopamine receptor D2 in rat striatal membrane was d...	-
Dopamine receptors; D1 & D2	IC50	=	1.7	nM	8.77	In vitro binding affinity to Dopamine receptor D1/Dopamine receptor D2 in rat st...	-
D(2) dopamine receptor	IC50	=	1.7	nM	8.77	In vitro agonist binding affinity was determined by displacing the [3H]N-propyln...	-
D(2) dopamine receptor	EC50	=	1.8	nM	8.74	In vitro effective concentration tested on HEK293 cells co-transfected with ferr...	15239663
Dopamine receptor	IC50	=	1.8	nM	8.74	Inhibitory concentration half-maximal displacement of 1.0 nM [3H]NPA specific bi...	7200145
D(2) dopamine receptor	EC50	=	1.8	nM	8.74	Agonist activity at ferret D2 receptor in HEK293 cells coexpressing Galphaqo5 by...	17149874

Literature References

PubMed	DOI	Target Context	# Activities
31158845	10.1038/s41586-019-1291-3	ADMET	75
-	10.5281/zenodo.13943903	ADMET	70
3989821	10.1021/jm50001a014	Mus musculus	38
3989821	10.1021/jm50001a014	ADMET	21
8097537	10.1021/jm00060a014	Mus musculus	16
8097538	10.1021/jm00060a015	Mus musculus	16
3989821	10.1021/jm50001a014	Albumin	16
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
556776	10.1021/jm00212a002	Rattus norvegicus	14
29429575	10.1016/j.bmc.2018.01.028	Amyloid-beta precursor protein	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
29429575	10.1016/j.bmc.2018.01.028	No relevant target	9
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
7205882	10.1021/jm00134a005	Felis catus	8
32184974	10.1021/acsmedchemlett.9b00575	D(1A) dopamine receptor	7
17417631	10.1038/nchembio873	NON-PROTEIN TARGET	7
17149874	10.1021/jm060662k	D(2) dopamine receptor	7
942751	10.1021/jm00223a006	Rattus norvegicus	7
32184974	10.1021/acsmedchemlett.9b00575	D(2) dopamine receptor	7
8064801	10.1021/jm00043a013	Rattus norvegicus	7

Data from ChEMBL 36 via Core Engine