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Compound Detail

CHEMBL959

RIMANTADINE
💊 Approved Drug
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💊 Approved Drug
CC(N)C12CC3CC(CC(C3)C1)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL959
Name RIMANTADINE
Phase Approved
Structure Type MOL
InChI Key UBCHPRBFMUDMNC-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Rimantadina Rimantadine
14
Targets
112
Activities
3
Assay Types
5
PK Parameters
20
Publications
2
Known Names
1
Indications

Molecular Properties

179.3
MW (Da)
2.55
ALogP
1
HBA
1
HBD
26.0
PSA (Ų)
0.66
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1993
Availability Prescription
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Stem -mantadine
USAN Year 1966

Extended Properties

Molecular Formula C12H21N
MW 179.31
Aromatic Rings 0
Heavy Atoms 13
NP-Likeness 0.19

Indications

Virus Diseases

ATC Classification

J05AC02
rimantadine
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

EC50 76 meas. best 8.0
IC50 32 meas. best 7.52
Kd 4 meas. best 7.8

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Influenza A virus
CHEMBL613740
 EC50 8.0 5.4706 10.0 48
Influenza A virus H3N2
CHEMBL2366902
 EC50 8.0 6.955 10.0 6
Matrix protein 2
CHEMBL1932894
 Kd 7.8 7.045 16.0 2
Unchecked
CHEMBL612545
 EC50 7.8 7.8 16.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 7.7 6.6571 20.0 7
Unchecked
CHEMBL612545
 IC50 7.52 5.705 30.0 4
Plasmodium yoelii yoelii
CHEMBL612328
 IC50 7.45 7.45 35.6 2
Influenza A virus
CHEMBL613740
 IC50 7.4 4.9111 40.0 9
H3N2 subtype
CHEMBL613193
 EC50 7.29 6.795 51.0 8
Matrix protein 2
CHEMBL2052
 Kd 6.29 5.725 510.0 2
Solute carrier family 22 member 2
CHEMBL1743122
 IC50 5.36 5.36 4400.0 1
Trypanosoma brucei
CHEMBL612849
 IC50 5.16 5.1525 7000.0 8
Multidrug and toxin extrusion protein 1
CHEMBL1743126
 IC50 5.14 5.14 7300.0 1
Matrix protein 2
CHEMBL2052
 IC50 4.97 4.97 10800.0 2
Polymerase acidic protein
CHEMBL1169598
 IC50 4.96 4.96 11000.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.36 4.36 44000.0 1
Influenza A virus (A/Puerto Rico/8/1934(H1N1))
CHEMBL612610
 EC50 4.21 4.21 62000.0 1
MDCK
CHEMBL614068
 EC50 4.18 4.18 66700.0 1
Influenza A virus (A/Puerto Rico/8/1934(H1N1))
CHEMBL612610
 IC50 4.17 4.17 67000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1200.0 ng.hr.mL-1 Oryctolagus cuniculus
CL 233.33 mL.min-1.kg-1 Oryctolagus cuniculus
MRT 0.32 hr Oryctolagus cuniculus
T1/2 0.5 hr Oryctolagus cuniculus
T1/2 24.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Influenza A virus H3N2 EC50 = 10.0 nM 8.0 Antiviral activity against Influenza A virus (A/HK/7/87(H3N2)) infected in dog M... 31586832
Influenza A virus H3N2 EC50 = 10.0 nM 8.0 Antiviral activity against Influenza A virus (A/HK/7/87(H3N2)) infected in dog M... 31586832
Influenza A virus EC50 = 10.0 nM 8.0 Antiviral activity against influenza A virus H3N3 subtype infected in dog MDCK c... 23811093
Unchecked EC50 = 16.0 nM 7.8 Antiviral activity against Influenza A virus A//HK/7/87 (H3N2) expressing wild-t... 28418242
Matrix protein 2 Kd = 16.0 nM 7.8 Binding affinity to Influenza A Weybridge(H7N7) virus Matrix protein 2 by spectr... 20570509
NON-PROTEIN TARGET EC50 = 20.0 nM 7.7 Antiviral activity against Influenza A virus (A/HK/7/87(H3N2)) infected in MDCK ... 25899336
Unchecked IC50 = 30.0 nM 7.52 Determination of Antiviral Activity: The cytopathic effect (CPE) inhibition test... -
Plasmodium yoelii yoelii IC50 = 35.6 nM 7.45 Antimalarial activity against liver stages of Plasmodium yoelii yoelii 22122518
Plasmodium yoelii yoelii IC50 = 35.6 nM 7.45 Antimicrobial activity against Plasmodium yoelii 265 liver infected in mammalian... 18212104
Influenza A virus EC50 = 40.0 nM 7.4 Antiviral activity against Influenza A virus A/WSN/33 H1N1 harboring N31S mutant... 29541360
Influenza A virus IC50 = 40.0 nM 7.4 Antiviral activity against amantadine-sensitive influenza A virus A/WSN/33-M2-N3... 28217261
NON-PROTEIN TARGET EC50 = 46.0 nM 7.34 Antiviral activity against Influenza A virus (A/HK/7/1987(H3N2)) infected in MDC... 24974341
Influenza A virus EC50 = 50.0 nM 7.3 Antiviral activity against Influenza A virus (A/Hong Kong/68(H3N2)) infected in ... 29541360
Influenza A virus IC50 = 50.0 nM 7.3 Antiviral activity against amantadine-sensitive influenza A virus A/Udorn/72 (H3... 28217261
Influenza A virus EC50 = 50.0 nM 7.3 Antiviral activity against Influenza A virus A/Ned/378/05(H1N1) infected in MDCK... 28477572
Influenza A virus EC50 = 50.0 nM 7.3 Antiviral activity against influenza virus H3N2 infected in dog MDCK cells asses... 37252100
NON-PROTEIN TARGET EC50 = 51.0 nM 7.29 Antiviral activity against Influenza A virus (A/HK/7/1987(H3N2)) infected in MDC... 24974341
H3N2 subtype EC50 = 51.0 nM 7.29 Antiviral activity against Influenza A virus (A/Hong Kong/7/1987(H3N2)) H1N1 inf... 23099097
Influenza A virus H3N2 EC50 = 80.0 nM 7.1 Antiviral activity against Influenza A virus H3N2 infected MDCK cells assessed a... 32214762
Influenza A virus EC50 = 90.0 nM 7.05 Antiviral activity against Influenza A virus A/Udorn/72 H3N2 infected in MDCK ce... 29541360

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 66
16472241 10.2174/1570163043334794 Hepatotoxicity 18
29541360 10.1021/acsmedchemlett.7b00458 Matrix protein 2 16
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20194696 10.1128/aac.01186-09 Influenza A virus 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
28217261 10.1021/acsmedchemlett.6b00311 Matrix protein 2 6
20194696 10.1128/aac.01186-09 Oryctolagus cuniculus 5
2362279 10.1021/jm00169a029 MDCK 5
24900429 10.1021/ml300279b Influenza A virus 5
29541360 10.1021/acsmedchemlett.7b00458 Influenza A virus 5
24237039 10.1021/jm401340p H3N2 subtype 4
23117173 10.1016/j.bmc.2012.09.064 Influenza A virus 4
20971531 10.1016/j.ejmech.2010.09.065 Influenza A virus 4
25899336 10.1016/j.ejmech.2015.04.030 NON-PROTEIN TARGET 4
24974341 10.1016/j.bmcl.2014.06.018 Influenza A virus 4
20381348 10.1016/j.bmcl.2010.03.080 Influenza A virus 4
10617092 10.1016/s0960-894x(99)00631-9 MDCK 4

Data from ChEMBL 36 via Core Engine