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Compound Detail

CHEMBL1643

RIBAVIRIN
💊 Approved Drug
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💊 Approved Drug
NC(=O)c1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)n1

Basic Information

ChEMBL ID CHEMBL1643
Name RIBAVIRIN
Phase Approved
Structure Type MOL
InChI Key IWUCXVSUMQZMFG-AFCXAGJDSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL398463

Known Names

Copegus Cotronak NSC-163039 Rebetol Ribapak Ribasphere Ribavarin Ribavirin Ribavirin biopartners Ribavirin mylan Ribavirin mylan (previously ribavirin three rivers) Ribavirin teva +10 more
74
Targets
697
Activities
4
Assay Types
7
PK Parameters
20
Publications
22
Known Names
20
Indications
3
Mechanisms

Molecular Properties

244.2
MW (Da)
-3.01
ALogP
8
HBA
4
HBD
143.7
PSA (Ų)
0.44
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1985
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Topical

Flags

Black Box Warning Natural Product Prodrug
USAN Stem -vir-
USAN Year 1974

Extended Properties

Molecular Formula C8H12N4O5
MW 244.21
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness 0.69

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Inosine-5'-monophosphate dehydrogenase 1 inhibitor INHIBITOR Inosine-5'-monophosphate dehydrogenase 1
RNA-directed RNA polymerase inhibitor INHIBITOR RNA-directed RNA polymerase
RNA inhibitor INHIBITOR RNA

Indications

Fibrosis Fibrosis Hepatitis C, Chronic Liver Cirrhosis Virus Diseases Depressive Disorder Hepatitis Hepatitis B, Chronic Hepatitis B, Chronic Hepatitis C HIV Infections Infections Respiratory Syncytial Virus Infections Severe Acute Respiratory Syndrome Severe Acute Respiratory Syndrome Diabetes Mellitus, Type 1 Encephalitis, Japanese Hemorrhagic Fever with Renal Syndrome Hepatitis D Influenza, Human

ATC Classification

J05AP01
ribavirin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
hematological toxicity
Country: United States
Black Box Warning
teratogenicity
Country: United States
Black Box Warning
respiratory toxicity
Country: United States
Black Box Warning
carcinogenicity
Country: United States
Black Box Warning
dermatological toxicity
Country: United States

Activity Summary

EC50 514 meas. best 8.3
IC50 180 meas. best 8.7
Ki 2 meas. best 5.35
Kd 1 meas. best 5.08

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Influenza A virus
CHEMBL613740
IC50 8.7 5.026 2.0 42
E6SM
CHEMBL614149
EC50 8.3 5.63 5.0 3
Hepatitis C virus
CHEMBL379
IC50 7.4 4.9314 40.0 7
Vesicular stomatitis virus
CHEMBL613739
IC50 7.34 7.34 46.0 1
Respiratory syncytial virus
CHEMBL612679
IC50 7.1 5.1086 80.0 7
Influenza B virus
CHEMBL613129
EC50 7.03 5.3 94.0 53
ADMET
CHEMBL612558
EC50 6.17 5.995 670.0 2
Unchecked
CHEMBL612545
IC50 6.0 5.264 1000.0 5
Influenza A virus
CHEMBL613740
EC50 5.98 5.0109 1050.0 138
BHK-21
CHEMBL614527
EC50 5.96 5.96 1100.0 1
dengue virus type 2
CHEMBL613966
EC50 5.94 4.8186 1160.0 7
Human orthopneumovirus
CHEMBL613127
EC50 5.92 5.36 1200.0 3
Bovine viral diarrhea virus 1
CHEMBL612571
EC50 5.89 5.2278 1300.0 9
NON-PROTEIN TARGET
CHEMBL3879801
EC50 5.89 5.0809 1300.0 11
Influenza A virus H3N2
CHEMBL2366902
EC50 5.85 5.1755 1400.0 11
HeLa
CHEMBL399
EC50 5.82 5.82 1500.0 1
Chikungunya virus
CHEMBL4296563
EC50 5.72 5.37 1890.0 5
Respiratory syncytial virus
CHEMBL612679
EC50 5.7 4.95 2000.0 37
Zika virus
CHEMBL4296612
IC50 5.66 5.224 2200.0 5
Junin virus
CHEMBL4523072
EC50 5.6 4.948 2500.0 5
Zika virus
CHEMBL4296612
EC50 5.59 4.741 2550.0 10
Chikungunya virus
CHEMBL4296563
IC50 5.51 5.51 3060.0 1
A-431
CHEMBL614069
IC50 5.5 5.5 3180.0 1
Mammarenavirus choriomeningitidis
CHEMBL5291622
EC50 5.46 5.46 3500.0 1
B16-F10
CHEMBL612656
IC50 5.46 5.46 3500.0 1
MDCK
CHEMBL614068
EC50 5.43 5.43 3700.0 1
Unchecked
CHEMBL612545
EC50 5.41 4.8669 3900.0 13
dengue virus type 2
CHEMBL613966
IC50 5.4 5.2157 4000.0 7
H5N1 subtype
CHEMBL613845
EC50 5.37 4.755 4300.0 6
Adenosine receptor A1
CHEMBL3688
Ki 5.35 5.35 4430.0 1
Yellow fever virus
CHEMBL613731
EC50 5.31 4.93 4900.0 2
MDCK
CHEMBL614068
IC50 5.31 5.05 4900.0 2
Vesicular stomatitis virus
CHEMBL613739
EC50 5.3 4.7107 5000.0 15
Sindbis virus
CHEMBL613725
EC50 5.29 4.795 5120.0 2
Hepatitis C virus
CHEMBL379
EC50 5.25 4.4738 5600.0 24
MOLT-4
CHEMBL614177
IC50 5.24 5.24 5700.0 1
H3N2 subtype
CHEMBL613193
EC50 5.23 5.11 5900.0 9
dengue virus type 1
CHEMBL613360
IC50 5.18 5.18 6660.0 1
West Nile virus
CHEMBL613730
IC50 5.17 4.7433 6700.0 3
SARS-CoV-2
CHEMBL4303835
EC50 5.15 5.15 7100.0 1
Adenosine receptor A1
CHEMBL226
Ki 5.13 5.13 7410.0 1
Influenza B virus
CHEMBL613129
IC50 5.1 4.6971 8000.0 7
Eukaryotic translation initiation factor 4E
CHEMBL4848
Kd 5.08 5.08 8400.0 1
Mus musculus
CHEMBL375
EC50 5.08 4.785 8300.0 2
Influenza A virus (A/Puerto Rico/8/1934(H1N1))
CHEMBL612610
EC50 5.06 4.7633 8700.0 3
Human alphaherpesvirus 1
CHEMBL377
IC50 5.0 5.0 10000.0 1
Human alphaherpesvirus 1
CHEMBL377
EC50 5.0 5.0 10000.0 1
Tacaribe virus
CHEMBL613131
EC50 5.0 4.69 10000.0 3
Influenza A virus H3N2
CHEMBL2366902
IC50 4.97 4.835 10600.0 2
Human respirovirus 3
CHEMBL613126
IC50 4.97 4.97 10700.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 248.7 - Chlorocebus sabaeus
CL 5.2 mL.min-1.kg-1 Homo sapiens
CL 5.2 mL.min-1.kg-1 Homo sapiens
F 64.0 % Homo sapiens
Fu 1.0 - Homo sapiens
MRT 45.0 hr Homo sapiens
T1/2 45.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Influenza A virus IC50 = 2.0 nM 8.7 Antiviral activity against VSV-G pseudotyped Influenza A virus infected in human... 28530828
E6SM EC50 = 5.0 nM 8.3 Effective concentration required to inhibit Herpes simplex virus-1(HSV-1) / thym... 11495586
Hepatitis C virus IC50 = 40.0 nM 7.4 Antiviral activity against Hepatitis C virus infected in African green monkey Ve... 27262598
Vesicular stomatitis virus IC50 = 46.0 nM 7.34 Antiviral activity against Vesicular stomatitis virus infected in African green ... 39126395
Respiratory syncytial virus IC50 = 80.0 nM 7.1 Antiviral activity against RSV infected in human HEp-2 cells assessed as inhibit... 32937282
Influenza B virus EC50 = 94.0 nM 7.03 Antiviral activity against Influenza B virus (B/HK/5/72) infected in MDCK cells ... 23117173
Influenza B virus EC50 = 140.0 nM 6.85 Antiviral activity against Influenza B virus (B/HK/5/72) infected in MDCK cells ... 23117173
Influenza A virus IC50 = 410.0 nM 6.39 Antiviral activity against Influenza A virus A/Hong Kong/8/68(H3N2) infected in ... 23806112
ADMET EC50 = 670.0 nM 6.17 Anti BVDV activity in MDBK (Madin-darby bovine kidney) cells 15456271
Unchecked IC50 = 1000.0 nM 6.0 Inhibition of IMPDH in mouse L1210 cells assessed as formation of [2,8-3H]hypoxa... 22555152
Unchecked IC50 = 1000.0 nM 6.0 Inhibition of IMPDH in human CEM cells assessed as formation of [2,8-3H]hypoxant... 22555152
Influenza A virus IC50 = 1050.0 nM 5.98 Antiviral activity against OSV-resistant influenza A virus A/LiaoNing-ZhenXing/1... 25681711
Influenza A virus EC50 = 1050.0 nM 5.98 Antiviral activity against oseltamivir-resistant influenza A virus LN/1109 (H1N1... 26686929
BHK-21 EC50 = 1100.0 nM 5.96 Inhibition of West Nile virus VLP replicon in BHK21 cell line 16539402
Influenza A virus EC50 = 1100.0 nM 5.96 Antiviral activity against influenza A virus H3N3 subtype infected in dog MDCK c... 23811093
dengue virus type 2 EC50 = 1160.0 nM 5.94 Antiviral activity against Dengue virus 2 infected in hamster BHK-21 cells incub... 36764470
Human orthopneumovirus EC50 = 1200.0 nM 5.92 Antiviral activity against Human respiratory syncytial virus A2 ATCC VR 1540 inf... 29028528
NON-PROTEIN TARGET EC50 = 1300.0 nM 5.89 Antiviral activity against Bovine viral diarrhea virus 1 infected in MDBK cells 27191614
NON-PROTEIN TARGET EC50 = 1300.0 nM 5.89 Antiviral activity against BVDV NADL infected in MDBK cells assessed as inhibiti... 27161176
Bovine viral diarrhea virus 1 EC50 = 1300.0 nM 5.89 Antiviral activity against BVDV AV-69 infected in MDBK cells assessed as cytopat... 24745970

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 443
17606691 10.1128/aac.00356-07 Punta Toro virus 51
17606691 10.1128/aac.00356-07 Pichinde virus 36
20231094 10.1016/j.bmcl.2010.02.074 ADMET 24
34256126 10.1016/j.ejmech.2021.113684 Respiratory syncytial virus 21
16472241 10.2174/1570163043334794 Hepatotoxicity 18
35306290 10.1016/j.ejmech.2022.114275 Zika virus 16
17938182 10.1128/aac.00863-07 Hepatitis C virus 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
218010 10.1021/jm00188a013 Influenza A virus 12
28408228 10.1016/j.bmcl.2017.03.100 Human alphaherpesvirus 1 12
37517205 10.1016/j.ejmech.2023.115660 Influenza A virus 11
2552118 10.1021/jm00130a024 Vaccinia virus 11
17576833 10.1128/aac.00211-07 Respiratory syncytial virus 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
- 10.1016/S0960-894X(97)10154-8 MDCK 10
1324318 10.1021/jm00095a019 ADMET 10
34273661 10.1016/j.ejmech.2021.113683 ADMET 10
20231094 10.1016/j.bmcl.2010.02.074 Influenza A virus 9
20421393 10.1128/aac.00010-10 Equilibrative nucleoside transporter 1 9

Data from ChEMBL 36 via Core Engine