Compound Detail

CHEMBL660

AMANTADINE

💊 Approved Drug

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💊 Approved Drug

NC12CC3CC(CC(C3)C1)C2

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL660
Name	AMANTADINE
Phase	Approved
Structure Type	MOL
InChI Key	DKNWSYNQZKUICI-UHFFFAOYSA-N
Therapeutic	✓ Yes

Known Names

Amantadina Amantadine Amantidine NSC-341865 TCMDC-125869

Targets

187

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

151.2

MW (Da)

1.91

ALogP

HBA

HBD

26.0

PSA (Å²)

0.56

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1968
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral

Flags

Natural Product

USAN Stem	-mantadine
USAN Year	1964

Extended Properties

Molecular Formula	C10H17N
MW	151.25
Aromatic Rings	0
Heavy Atoms	11
NP-Likeness	0.55

Indications

Parkinson Disease Brain Injuries Hepatitis C, Chronic Multiple Sclerosis Psychotic Disorders Schizophrenia Severe Acute Respiratory Syndrome Attention Deficit Disorder with Hyperactivity Cerebral Infarction Cocaine-Related Disorders Diabetes Mellitus, Type 2 Hepatitis C Infections Influenza, Human Pain Stroke Mental Disorders Mood Disorders

ATC Classification

N04BB01

amantadine

Level 1: NERVOUS SYSTEM

Level 2: ANTI-PARKINSON DRUGS

Activity Summary

EC50 108 meas. best 7.52

IC50 63 meas. best 6.57

Kd 10 meas. best 6.5

Ki 6 meas. best 7.69

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Sigma non-opioid intracellular receptor 1 CHEMBL287	Ki	7.69	7.69	20.2	1
Influenza A virus H3N2 CHEMBL2366902	EC50	7.52	5.657	30.0	10
NON-PROTEIN TARGET CHEMBL3879801	EC50	7.4	5.9945	40.0	11
Unchecked CHEMBL612545	EC50	7.0	6.0933	100.0	3
Influenza A virus CHEMBL613740	EC50	6.64	5.1259	230.0	56
Unchecked CHEMBL612545	IC50	6.57	5.0813	270.0	8
Matrix protein 2 CHEMBL1932894	Kd	6.5	6.08	320.0	2
Influenza A virus CHEMBL613740	IC50	6.48	5.375	330.0	14
H3N2 subtype CHEMBL613193	EC50	6.4	5.851	400.0	10
Influenza A virus H3N2 CHEMBL2366902	IC50	6.3	6.25	500.0	2
Matrix protein 2 CHEMBL2052	EC50	6.18	6.18	660.0	2
MDCK CHEMBL614068	EC50	5.96	5.96	1100.0	1
Matrix protein 2 CHEMBL2052	Kd	5.66	5.21	2170.0	3
Unchecked CHEMBL612545	Kd	5.66	5.445	2170.0	4
H5N1 subtype CHEMBL613845	IC50	5.42	5.42	3840.0	1
Matrix protein 2 CHEMBL2052	IC50	5.33	4.955	4700.0	4
Plasmodium falciparum CHEMBL364	IC50	5.25	5.25	5670.0	1
Glutamate NMDA receptor; GRIN1/GRIN2A CHEMBL1907604	Ki	5.0	5.0	10000.0	1
Unchecked CHEMBL612545	Ki	5.0	4.8733	10000.0	3
Glutamate [NMDA] receptor CHEMBL2094124	Ki	4.98	4.98	10500.0	1
NON-PROTEIN TARGET CHEMBL3879801	IC50	4.97	4.97	10780.0	1
Matrix protein 2 CHEMBL1932894	IC50	4.8	4.8	16000.0	1
Solute carrier family 22 member 2 CHEMBL1743122	IC50	4.64	4.49	23000.0	2
Multidrug and toxin extrusion protein 1 CHEMBL1743126	IC50	4.42	4.42	37800.0	1
Solute carrier family 22 member 1 CHEMBL5685	IC50	4.4	4.4	39600.0	1
Glutamate NMDA receptor; Grin1/Grin2a CHEMBL2096680	IC50	4.4	4.4	40000.0	1
Influenza A virus (A/Puerto Rico/8/1934(H1N1)) CHEMBL612610	EC50	4.36	4.36	44000.0	1
Influenza B virus CHEMBL613129	IC50	4.3	4.3	50000.0	1
Trypanosoma brucei rhodesiense CHEMBL612348	IC50	4.28	4.28	52760.0	1
Influenza A virus (A/Puerto Rico/8/1934(H1N1)) CHEMBL612610	IC50	4.19	4.19	64000.0	1
Solute carrier family 22 member 1 CHEMBL2073670	IC50	4.12	4.12	76300.0	1
Glutamate NMDA receptor CHEMBL1907608	IC50	4.04	4.04	92000.0	4

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	4.8	mL.min-1.kg-1	Homo sapiens
CL	4.8	mL.min-1.kg-1	Homo sapiens
CL	-	mL.min-1.kg-1	Homo sapiens
CL	4.8	mL.min-1.kg-1	Homo sapiens
F	79.0	%	Homo sapiens
Fu	0.33	-	Homo sapiens
Fu	0.233	-	Rattus norvegicus
Fu	0.33	-	Homo sapiens
Fu	0.33	-	Homo sapiens
Fu	0.29	-	Rattus norvegicus
Fu	0.171	-	Homo sapiens
Fu	0.1	-	Macaca fascicularis
Fu	0.218	-	Canis lupus familiaris
Fu	0.178	-	Cavia porcellus
Fu	0.181	-	Mus musculus
Fu	0.147	-	Rattus norvegicus
Fu	0.213	-	Rattus norvegicus
MRT	23.0	hr	Homo sapiens
T1/2	16.0	hr	Homo sapiens
Vd	9.9	L.kg-1	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Sigma non-opioid intracellular receptor 1	Ki	=	20.25	nM	7.69	Binding affinity towards sigma receptor in guinea pig brain membrane was determi...	-
Influenza A virus H3N2	EC50	=	30.0	nM	7.52	Antiviral activity against Influenza A virus (A/HK/7/87(H3N2)) infected in dog M...	31586832
NON-PROTEIN TARGET	EC50	=	40.0	nM	7.4	Antiviral activity against Influenza A virus A/Puerto Rico/8/34 expressing wild ...	27187859
Unchecked	EC50	=	100.0	nM	7.0	Inhibition of Influenza A virus A/udorn/72(H3N2) wild type M2 proton channel exp...	27187859
Unchecked	EC50	=	140.0	nM	6.85	Antiviral activity against Influenza A virus A//HK/7/87 (H3N2) expressing wild-t...	28418242
NON-PROTEIN TARGET	EC50	=	140.0	nM	6.85	Antiviral activity against Influenza A virus (A/HK/7/87(H3N2)) infected in MDCK ...	25899336
Influenza A virus H3N2	EC50	=	200.0	nM	6.7	Antiviral activity against Influenza A virus (A/HK/7/87(H3N2)) infected in dog M...	31586832
Influenza A virus	EC50	=	230.0	nM	6.64	Antiviral activity against Influenza A virus (A/chicken/Hubei/327/2004(H5N1)) in...	30292897
Unchecked	IC50	=	270.0	nM	6.57	Antiviral activity against Influenza A virus (A/WSN/1933(H1N1)) expressing M2 pr...	28107633
Influenza A virus	EC50	=	300.0	nM	6.52	Antiviral activity against influenza A virus H3N3 subtype infected in dog MDCK c...	23811093
Influenza A virus	EC50	=	300.0	nM	6.52	Antiviral activity against Influenza A virus A/udorn/72(H3N2) expressing wild ty...	26771709
Matrix protein 2	Kd	=	320.0	nM	6.5	Binding affinity to Influenza A Weybridge(H7N7) virus Matrix protein 2 by spectr...	20570509
Influenza A virus	IC50	=	330.0	nM	6.48	Antiviral activity against amantadine-sensitive influenza A virus A/Udorn/72 (H3...	28217261
Influenza A virus	EC50	=	340.0	nM	6.47	Antiviral activity against Influenza A virus A2/Taiwan/1/64(H2N2) infected in MD...	24793875
H3N2 subtype	EC50	=	400.0	nM	6.4	Antiviral activity against Influenza A virus (A/Hong Kong/7/87(H3N2)) assessed a...	19791806
Influenza A virus	EC50	=	430.0	nM	6.37	Antiviral activity against amantadine-sensitive Influenza A virus (A/chicken/Hub...	31559005
H3N2 subtype	EC50	=	450.0	nM	6.35	Antiviral activity against Influenza A virus (A/Hong Kong/7/1987(H3N2)) H1N1 inf...	23099097
NON-PROTEIN TARGET	EC50	=	450.0	nM	6.35	Antiviral activity against Influenza A virus (A/HK/7/1987(H3N2)) infected in MDC...	24974341
Influenza A virus	IC50	=	480.0	nM	6.32	Antiviral activity against amantadine-sensitive influenza A virus A/WSN/33-M2-N3...	28217261
Influenza A virus	EC50	=	480.0	nM	6.32	Antiviral activity against Influenza A virus A/WSN/33 H1N1 harboring N31S mutant...	29541360

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	405
-	10.5281/zenodo.13943903	ADMET	89
31158845	10.1038/s41586-019-1291-3	ADMET	62
16472241	10.2174/1570163043334794	Hepatotoxicity	18
29541360	10.1021/acsmedchemlett.7b00458	Matrix protein 2	18
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
28107633	10.1021/acs.jmedchem.6b01115	Unchecked	10
28107633	10.1021/acs.jmedchem.6b01115	Matrix protein 2	8
20070106	10.1021/jm901371v	Homo sapiens	8
490532	10.1021/jm00194a025	unidentified influenza virus	7
24941437	10.1021/jm5005804	Matrix protein 2	6
28217261	10.1021/acsmedchemlett.6b00311	Matrix protein 2	6
21466220	10.1021/jm101334y	Matrix protein 2	6
25019388	10.1021/jm5007275	NON-PROTEIN TARGET	6
24793875	10.1021/jm500598u	Influenza A virus	6
27187859	10.1016/j.ejmech.2016.05.008	NON-PROTEIN TARGET	6
21474681	10.1124/dmd.111.038778	Brain	5
2362279	10.1021/jm00169a029	MDCK	5
10476872	10.1016/s0960-894x(99)00395-9	ADMET	5
24900429	10.1021/ml300279b	Influenza A virus	5

Data from ChEMBL 36 via Core Engine