Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1413)
Drug Name
Ribavirin
Synonyms
Rebetol; Rebetron; Rebretron; Ribamide; Ribamidil; Ribamidyl; Ribasphere; Ribavirin (Copegus); Ribavirin Capsules; Ribavirina; Ribavirina [INN-Spanish]; Ribavirine; Ribavirine [INN-French]; Ribavirinum; Ribavirinum [INN-Latin]; Tribavirin; Copegus; ICN-1229; Varazid; Vilona; Viramid; Virazid; Virazole; ribavirin; 1-beta-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide; 1-beta-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide; 36791-04-5; DRG-0028; RTCA; Ribav; UNII-49717AWG6K
Indication Viral hepatitis [ICD11: 1E51] Approved [1]
Structure
3D MOL 2D MOL
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
Cross-matching ID
PubChem CID
37542
PubChem SID
595938 ; 7847489 ; 7980513 ; 8139972 ; 8150084 ; 8175073 ; 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
ChEBI ID
CHEBI:63580
CAS Number
36791-04-5
TTD Drug ID
D0H3WI
Formula
C8H12N4O5
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
MP DM018378 N. A. Conjugation - Mono-phosphorylation 1 [5] , [6] , [2]
DP DM018379 N. A. Conjugation - Di-phosphorylation 2 [5] , [6]
TP DM018380 N. A. Conjugation - Triphosphorylation 3 [5] , [6]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR013140 Ribavirin MP Conjugation - Mono-phosphorylation ADK [5], [6], [2]
MR013141 MP DP Conjugation - Di-phosphorylation Unclear [5], [6]
MR013142 DP TP Conjugation - Triphosphorylation Unclear [5], [6]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Adenosine kinase (ADK) DME0448 Homo sapiens
ADK_HUMAN
2.7.1.20
[2]
Cytosolic 5'-nucleotidase II (NT5C2) DME0482 Homo sapiens
5NTC_HUMAN
3.1.3.5
[3]
Purine nucleoside phosphorylase (PNP) DME0437 Homo sapiens
PNPH_HUMAN
2.4.2.1
[4]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Cytosolic 5'-nucleotidase II (NT5C2) DME0482 Km = 0.024 microM
5NTC_HUMAN
[3]
References
1 Ribavirin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Adenosine kinase is a key determinant for the anti-HCV activity of ribavirin
3 Phosphorylation of ribavirin and viramidine by adenosine kinase and cytosolic 5'-nucleotidase II: Implications for ribavirin metabolism in erythrocytes. Antimicrob Agents Chemother. 2005 Jun;49(6):2164-71.
4 Functional analysis of purine nucleoside phosphorylase as a key enzyme in ribavirin metabolism. Drug Metab Pharmacokinet. 2014;29(2):211-4.
5 Pharmacokinetics and metabolism of [(14)C]ribavirin in rats and cynomolgus monkeys
6 Sofosbuvir and Ribavirin Liver Pharmacokinetics in Patients Infected with Hepatitis C Virus

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