Drug Information

General Information
Drug ID
DR00176
Drug Name
Ribavirin
Synonyms
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-1,2,4-triazole-3-carboxamide; 1-beta-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide; 1-beta-D-ribofuranosyl-1-H-1,2,4-triazole-3-carboxamide; AA-504/07617051; C-Virin; Copegus; Copegus (TN); Cotronak; DRG-0028; Drug: Ribavirin; ICN-1229; KS-1104; R 9644; R-964; RBV; RG-964; RTC; RTCA; Ravanex; Rebetol; Rebetol (TN); Rebetron; Rebretron; Ribacine; Ribamide; Ribamidil; Ribamidyl; Ribasphere; Ribasphere (TN); Ribav; Ribavirin (JAN/USP/INN); Ribavirin Capsules; Ribavirin [USAN:INN]; Ribavirina; Ribavirina [INN-Spanish]; Ribavirine; Ribavirine [INN-French]; Ribavirinum; Ribavirinum [INN-Latin]; Ribovirin; Ro 20-9963/000; Ro-20-9963; SCH 18908; Tribavirin; Varazid; Vilona; Vilona (TN); Viramid; Viramide; Virazid; Virazide; Virazole; Virazole (Ribavirin) Inhalation Solution; Virazole (TN)
Drug Type
Small molecular drug
Indication Hepatitis C virus infection [ICD11:1E50.2, 1E51.1] Approved [1]
Therapeutic Class
Antiviral Agents
Structure
3D MOL 2D MOL
Formula
C8H12N4O5
Canonical SMILES
C1=NC(=NN1C2C(C(C(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
CAS Number
CAS 36791-04-5
Pharmaceutical Properties Molecular Weight 244.2 Topological Polar Surface Area 144
Heavy Atom Count 17 Rotatable Bond Count 3
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 7
XLogP
-1.8
PubChem CID
37542
PubChem SID
11335957 ,11361196 ,11364740 ,11367302 ,11369864 ,11372951 ,11374942 ,11378029 ,11462168 ,11491691 ,11493066 ,11495640 ,11528313 ,12059582 ,14798456 ,15122005 ,17389529 ,17405619 ,24278685 ,25621753 ,26538475 ,26612558 ,26679740 ,34678832 ,46505883 ,47291173 ,47365228 ,47440296 ,47515344 ,47589035 ,47885447 ,47885448 ,48035157 ,48416516 ,48424047 ,48425596 ,48631153 ,49699015 ,50105410 ,50105411 ,50105412 ,50105413 ,50474786 ,53778169 ,595938 ,7847489 ,7980513 ,8139972 ,8150084 ,8175073
ChEBI ID
CHEBI:63580
TTD Drug ID
D0H3WI
DT(s) Transporting This Drug CNT2 Transporter Info Concentrative nucleoside transporter 2 Substrate [2]
CNT3 Transporter Info Concentrative Na(+)-nucleoside cotransporter 3 Substrate [3]
ENT1 Transporter Info Equilibrative nucleoside transporter 1 Substrate [4]
PEPT1 Transporter Info Peptide transporter 1 Substrate [5]
Drug-Transporter Activity Data
Drug-Transporter Activity Data CNT3 Transporter Info Km =28.2 microM Xenopus oocytes-hCNT3 and hENT1 [3]
References
1 Ribavirin was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 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.
3 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.
4 Effects of dipyridamole coadministration on the pharmacokinetics of ribavirin in healthy volunteers. Drug Metab Pharmacokinet. 2013;28(5):406-10.
5 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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