Drug Details

General Information of the Drug (ID: DR5724)
Name
Ribavirin
Synonyms
ribavirin; 36791-04-5; Tribavirin; Rebetol; Virazole; Copegus; Vilona; Ribavirine; Viramid; Ribamide; Ribamidil; Ribasphere; Ribavirina; Ribavirinum; Ribavirine [INN-French]; Ribavirinum [INN-Latin]; ICN-1229; Ribavirina [INN-Spanish]; 1-beta-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide; 1-beta-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide; RTCA; RBV; SCH 18908; UNII-49717AWG6K; Ribamidyl; Ribavirin (Copegus); 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide; 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-1,2,4-triazole-3-carboxamide; 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide; MFCD00058564; Rebetron; Varazid; Ribavirin Capsules; CHEBI:63580; 49717AWG6K; Ribavirin, 98%; 1-(beta-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide; Rebretron; Virazid; Virazide; Ribav; DSSTox_CID_3557; DSSTox_RID_77081; DSSTox_GSID_23557; RTC; 1-(beta-D-Ribofuranosyl)-1,2,4-triazole-3-carboxamide; Cotronak; Ravanex; Ribacine; NSC-163039; C-Virin; DRG-0028; Ribasphere (TN); Virazole (TN); SMR000058315; Copegus (TN); Rebetol (TN); HSDB 6513; SR-01000076112; BRN 0892462; Ribavirine;; NSC163039; Ribavirin [USAN:USP:INN:BAN]; Ribavirin,(S); NCGC00015904-02; Ribavirin, antiviral; CAS-36791-04-5; RG-964; PubChem14187; Ro-20-9963; Spectrum_001826; 1H-1,2,4-Triazole-3-carboxamide, 1-beta-D-ribofuranosyl-; 4pb1; ribofluranosyl carboxamide; Prestwick3_000993; Spectrum3_001876; Spectrum4_001252; Spectrum5_002075; R-964; R 9644; SCHEMBL3727; CHEMBL1643; Lopac0_001063; BSPBio_001085; BSPBio_003352; KBioGR_001804; KBioSS_002331; cid_37542; MLS000028486; MLS002222317; DivK1c_000782; SPECTRUM1503938; Ribavirin (JP17/USP/INN); BPBio1_001195; GTPL6842; 1,2,4-Triazole-3-carboxamide, 1-beta-D-ribofuranosyl-; 1-.beta.-D-Ribofuranosyl-1,2,4-triazolo-3-carboxamide; DTXSID8023557; HMS502H04; KBio1_000782; KBio2_002328; KBio2_004896; KBio2_007464; KBio3_002854; NINDS_000782; HMS2090L15; HMS2094O09; HMS2098G07; HMS2232P07; HMS3263E08; HMS3715G07; Pharmakon1600-01503938; HY-B0434; ZINC1035331; Tox21_110259; Tox21_200967; Tox21_501063; BDBM50154375; CCG-38985; NSC758650; s2504; SCH-18908; AKOS001715163; Tox21_110259_1; DB00811; GS-3572; LP01063; MCULE-9495128592; NSC-758650; SDCCGSBI-0051033.P004; IDI1_000782; SMP1_000261; NCGC00090726-01; NCGC00090726-03; NCGC00090726-04; NCGC00090726-05; NCGC00090726-06; NCGC00090726-07; NCGC00090726-08; NCGC00090726-09; NCGC00090726-12; NCGC00090726-25; NCGC00258520-01; NCGC00261748-01; 252269-50-4; AS-34178; BCP0726000138; SBI-0051033.P003; AB0068936; AB00430481; EU-0101063; R0077; EN300-59237; D00423; J10190; M-7546; AB00430481-15; AB00430481-16; AB00430481_17; AB00430481_18; 1-beta-Ribofuranosyl-1,2,4-triazole-3-carboamide; 791R045; Q421862; Ribavirin 100 microg/mL in Acetonitrile:Methanol; SR-01000721904; SR-01000076112-2; SR-01000076112-3; SR-01000076112-4; SR-01000721904-2; 1-??-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide; BRD-K60369935-001-02-7; BRD-K60369935-001-18-3; SR-01000076112-11; 1-?-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide; Ribavirin, British Pharmacopoeia (BP) Reference Standard; Z1522567185; 1-(beta -D-ribofuranosyl)-1,2,4-triazole-3-carboxamide; Ribavirin, European Pharmacopoeia (EP) Reference Standard; Ribavirin, United States Pharmacopeia (USP) Reference Standard; Ribavirin, Pharmaceutical Secondary Standard; Certified Reference Material; 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,2,4-triazole-3-carboxamide
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Molecular Type
Small molecule
Disease Hepatitis C virus infection [ICD-11: 1E51] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 2 h
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability
Bioavailability
60% of drug becomes completely available to its intended biological destination(s)
Clearance
The clearance of drug is 26 L/h
Clearance
The drug present in the plasma can be removed from the body at the rate of 5.2 mL/min/kg
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
Elimination
17% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 120 - 170 hours
Half-life
The concentration or amount of drug in body reduced by one-half in 45 hours
Metabolism
The drug is metabolized via the adenosine kinase
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 35.1 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 1%
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 14 L/kg
Water Solubility
The ability of drug to dissolve in water is measured as 142 mg/mL
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Formula
C8H12N4O5
PubChem CID
37542
Canonical SMILES
C1=NC(=NN1C2C(C(C(O2)CO)O)O)C(=O)N
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
CAS Number
CAS 36791-04-5
ChEBI ID
CHEBI:63580
TTD Drug ID
D0H3WI
DrugBank ID
DB00811
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Jerusalem artichoke + Interferon alpha-2a     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression BAX  Molecule Info 
Pathway MAP
Down-regulation Expression TGFB1  Molecule Info 
Pathway MAP
Down-regulation Expression TP53  Molecule Info 
Pathway MAP
                    In-vivo Model Male albino rats (150-200g) were used in this study.
                    Experimental
                    Result(s)		 Addition of JAT as a supportive regimen to interferon and ribavirin effectively potentiates their anti-fibrotic effects.
Target and Pathway
Target(s) IMP dehydrogenase 1 (IMPDH1)  Molecule Info  [3]
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6842).
Reference 2 Synergistic Effects of Jerusalem Artichoke in Combination with Pegylated Interferon Alfa-2a and Ribavirin Against Hepatic Fibrosis in Rats. Asian Pac J Cancer Prev. 2016;17(4):1979-85.
Reference 3 Treating HCV with ribavirin analogues and ribavirin-like molecules. J Antimicrob Chemother. 2006 Jan;57(1):8-13.
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