Details of the Drug

General Information of Drug (ID: DMEYLH9)

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], [2]
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) 3
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [3]
Bioavailability
60% of drug becomes completely available to its intended biological destination(s) [4]
Clearance
The drug present in the plasma can be removed from the body at the rate of 5.2 mL/min/kg [5]
Elimination
17% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 45 hours [5]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 35.1 micromolar/kg/day [6]
Unbound Fraction
The unbound fraction of drug in plasma is 1% [5]
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 [5]
Water Solubility
The ability of drug to dissolve in water is measured as 142 mg/mL [3]
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
D0H3WI
VARIDT ID
DR00176
INTEDE ID
DR1413
ACDINA ID
D00589

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Inosine-5'-monophosphate dehydrogenase 1 (IMPDH1) TTL7C8Q IMDH1_HUMAN Inhibitor [7], [8]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Equilibrative nucleoside transporter 1 (SLC29A1) DTXD1TQ S29A1_HUMAN Substrate [9]
Concentrative nucleoside transporter 2 (SLC28A2) DT82KPY S28A2_HUMAN Substrate [10]
Concentrative Na(+)-nucleoside cotransporter 3 (SLC28A3) DT4YL5R S28A3_HUMAN Substrate [11]
Peptide transporter 1 (SLC15A1) DT9G7XN S15A1_HUMAN Substrate [12]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Purine nucleoside phosphorylase (PNP) DE2WSAL PNPH_HUMAN Substrate [13]
Cytosolic 5'-nucleotidase II (NT5C2) DE1DOKJ 5NTC_HUMAN Substrate [14]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Ribavirin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Mercaptopurine DMTM2IK Major Decreased metabolism of Ribavirin caused by Mercaptopurine mediated inhibition of non-CYP450 enzyme. Mature B-cell lymphoma [2A85] [39]
Azathioprine DMMZSXQ Major Decreased metabolism of Ribavirin caused by Azathioprine mediated inhibition of non-CYP450 enzyme. Transplant rejection [NE84] [39]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
FD&C blue no. 1 E00263 19700 Colorant
FD&C blue no. 2 E00446 2723854 Colorant
Isopropyl alcohol E00070 3776 Antimicrobial preservative; Solvent
Mannitol E00103 6251 Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Sodium lauryl sulfate E00464 3423265 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Ammonia E00007 222 Alkalizing agent
Butyl alcohol E00011 263 Flavoring agent; Solvent
Carmellose sodium E00625 Not Available Disintegrant
Crospovidone E00626 Not Available Disintegrant
Eisenoxyd E00585 56841934 Colorant
Ferric hydroxide oxide yellow E00539 23320441 Colorant
Ferrosoferric oxide E00231 14789 Colorant
Hypromellose E00634 Not Available Coating agent
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate E00208 11177 lubricant
Polyethylene glycol 3350 E00652 Not Available Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polysorbate 80 E00665 Not Available Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Polyvinyl alcohol E00666 Not Available Coating agent; Emulsion stabilizing agent; Film/Membrane-forming agent
Povidone E00667 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
Triacetin E00080 5541 Humectant; Plasticizing agent; Solvent
Vinylpyrrolidone E00668 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Water E00035 962 Solvent
⏷ Show the Full List of 26 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Ribavirin 200 mg tablet 200 mg Oral Tablet Oral
Ribavirin 400 mg tablet 400 mg Oral Tablet Oral
Ribavirin 600 mg tablet 600 mg Oral Tablet Oral
Ribavirin 200 mg capsule 200 mg Oral Capsule Oral
Ribavirin 500 mg tablet 500 mg Oral Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

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6 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7 Treating HCV with ribavirin analogues and ribavirin-like molecules. J Antimicrob Chemother. 2006 Jan;57(1):8-13.
8 A randomized, double-blind, placebo-controlled dose-escalation trial of merimepodib (VX-497) and interferon-alpha in previously untreated patients with chronic hepatitis C. Antivir Ther. 2005;10(5):635-43.
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10 Identification and functional analysis of variants in the human concentrative nucleoside transporter 2, hCNT2 (SLC28A2) in Chinese, Malays and Indians. Pharmacogenet Genomics. 2007 Sep;17(9):783-6.
11 Kinetic study of anti-viral ribavirin uptake mediated by hCNT3 and hENT1 in Xenopus laevis oocytes. Biophys Chem. 2010 Mar;147(1-2):59-65.
12 Transport of levovirin prodrugs in the human intestinal Caco-2 cell line. J Pharm Sci. 2006 Jun;95(6):1318-25.
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24 Transport of ribavirin across the rat and human placental barrier: Roles of nucleoside and ATP-binding cassette drug efflux transporters. Biochem Pharmacol. 2019 May;163:60-70.
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