Details of the Drug

General Information of Drug (ID: DM2A1DP)

Drug Name

Ribavirin

Synonyms

ribavirin; 36791-04-5; Tribavirin; Rebetol; Virazole; Ribavirine; Copegus; Vilona; Ribamide; Ribasphere; Ribamidil; Viramid; Ribamidyl; Ribavirinum; Ribavirina; Rebetron; Varazid; RTCA; Ribavirin Capsules; Ribavirinum [INN-Latin]; Ribavirine [INN-French]; Ribavirina [INN-Spanish]; ICN-1229; Rebretron; Virazid; Ribav; 1-beta-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide; DRG-0028; 1-beta-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide; UNII-49717AWG6K; Ribavirin (Copegus); Copegus; Cotronak; RBV; RTC; Ravanex; Ribacine; Ribovirin; Viramide; Virazide; R 9644; SCH 18908; C-Virin; Copegus (TN); Drug: Ribavirin; KS-1104; R-964; RG-964; Rebetol (TN); Ribasphere (TN); Ribavirin [USAN:INN]; Vilona (TN); Virazole (Ribavirin) Inhalation Solution; Virazole (TN); AA-504/07617051; Ro 20-9963/000; Ro-20-9963; Ribavirin (JAN/USP/INN); 1-beta-D-Ribofuranosyl-1,2,4-triazolo-3-carboxamide; 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide; 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide; 1-beta-D-ribofuranosyl-1-H-1,2,4-triazole-3-carboxamide; RBI034 (2-5A antisense compound) + Ribavirin

Indication

Disease Entry	ICD 11	Status	REF
Hepatitis C virus infection	1E51.1	Approved	[1]
Coronavirus Disease 2019 (COVID-19)	1D6Y	Investigative	[2]
Middle East Respiratory Syndrome (MERS)	1D64	Investigative	[3]
Severe acute respiratory syndrome (SARS)	1D65	Investigative	[4], [3]

Therapeutic Class

Antiviral Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

244.2

Topological Polar Surface Area (xlogp)

-1.8

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Tmax: The time to maximum plasma concentration (Tmax) is 2 h [5]
Clearance: The clearance of drug is 26 L/h [6]
Elimination: After the oral administration of 600mg radiolabeled ribavirin, approximately 61% of the drug was detected in the urine and 12% was detected in the feces [5]
Half-life: The concentration or amount of drug in body reduced by one-half in 120 - 170 hours [7]
Metabolism: The drug is metabolized via the adenosine kinase [5]

Chemical Identifiers

Formula: C8H12N4O5
IUPAC Name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide
Canonical SMILES: C1=NC(=NN1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)C(=O)N
InChI: InChI=1S/C8H12N4O5/c9-6(16)7-10-2-12(11-7)8-5(15)4(14)3(1-13)17-8/h2-5,8,13-15H,1H2,(H2,9,16)/t3-,4-,5-,8-/m1/s1
InChIKey: IWUCXVSUMQZMFG-AFCXAGJDSA-N

Cross-matching ID

PubChem CID: 37542
ChEBI ID: CHEBI:63580
CAS Number: 36791-04-5
DrugBank ID: DB00811
TTD ID: D0VI8H
ACDINA ID: D00589

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
HUMAN inosine-5'-monophosphate dehydrogenase 1 (IMPDH1)	TT3GRLK	IMDH1_HUMAN	Inhibitor	[2]
HUMAN inosine-5'-monophosphate dehydrogenase 2 (IMPDH2)	TTTU6X1	IMDH2_HUMAN	Inhibitor	[2]
MERS-CoV RNA-directed RNA polymerase (RdRp)	TTOA6YT	R1AB_CVEMC (4378-5310)	Inhibitor	[4]
SARS-CoV RNA-directed RNA polymerase (RdRp)	TTKXI53	R1AB_CVHSA (4370-5301)	Inhibitor	[4], [3]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	Proteomics of SARS-CoV-2-infected Host Cells Reveals Therapy Targets. Nature. 2020 May 14. doi: 10.1038/s41586-020-2332-7.
3	SARS and MERS: recent insights into emerging coronaviruses. Nat Rev Microbiol. 2016 Aug;14(8):523-34.
4	Coronaviruses - drug discovery and therapeutic options. Nat Rev Drug Discov. 2016 May;15(5):327-47.
5	FDA Approved Drug Products: Rebetol (ribavirin) oral capsules
6	An FDA phase I clinical trial of quinacrine sterilization (QS). Int J Gynaecol Obstet. 2003 Oct;83 Suppl 2:S45-9.
7	FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
8	The IMPDH inhibitor merimepodib suppresses SARS-CoV-2 replication in vitro. April 09, 2020. doi: https://doi.org/10.1101/2020.04.07.028589
9	Comparative therapeutic efficacy of remdesivir and combination lopinavir, ritonavir, and interferon beta against MERS-CoV. Nat Commun. 2020 Jan 10;11(1):222.
10	Design, Synthesis, and Anti-RNA Virus Activity of 6'-Fluorinated-Aristeromycin Analogues. J Med Chem. 2019 Jul 11;62(13):6346-6362.
11	Lycorine: A prospective natural lead for anticancer drug discovery. Biomed Pharmacother. 2018 Nov;107:615-624.