ContaminantDB: Ribavirin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:45:50 UTC

Update Date

2016-11-09 01:15:29 UTC

Accession Number

CHEM016864

Identification

Common Name

Ribavirin

Class

Small Molecule

Description

Producing a broad-spectrum activity against several RNA and DNA viruses, Ribavirin is a synthetic guanosine nucleoside and antiviral agent that interferes with the synthesis of viral mRNA. It is primarily indicated for use in treating hepatitis C and viral hemorrhagic fevers. HCV is a single-stranded RNA virus that is categorized into nine distinct genotypes, with genotype 1 being the most common in the United States, and affecting 72% of all chronic HCV patients . It is reported that ribavirin might be only effective in early stages of viral hemorrhagic fevers including Lasser fever, Crimean-Congo hemorrhagic fever, Venezuelan hemorrhagic fever, and Hantavirus infection. Ribavirin is a prodrug that is metabolized into nucleoside analogs that blocks viral RNA synthesis and viral mRNA capping. Before the development of newer drugs, ribavirin and / dual therapy was considered the first-generation and standard antiviral treatment . The dual therapy was administered for 48 weeks in patients with genotype 1, 4, 5, and 6, and 24 weeks in patients with genotype 2 and 3 . Newer drugs developed as Hepatitis C viral infection treatments can be used to reduce or eliminate the use of ribavirin, which are associated with serious adverse effects. They also improve therapeutic efficacy in patients with failed / and ribavirin-based therapy. The potential use of ribavirin as a treatment for acute myeloid leukemia is currently under investigation. According to 2017 American Association for the Study of Liver Diseases (AASLD) and 2015 consensus guidelines from the Canadian Association for the Study of the Liver (CASL), ribavirin is typically used as an adjunct therapy to various first-line and second-line combination therapies recommended for each genotypes. Ribavirin is added to decrease relapse rates by accelerating viral clearance early in the treatment course . When used to treat Hepatitis C virus (HCV) infections, it is always used as a part of combination therapies as ribavirin monotherapy is not efficacious in the treatment of chronic hepatitis C infection . Additionally, including ribavirin in the regimen can increase the risk of anemia. In HCV genotye 1/2/3/4/5/6 patients, ribavirin can be used in combination therapy involving and , Eplusa (, ), Harvoni (, ), and , Viekira Pak (, , , ), Technivie (, , ) and Zepatier (, ). Addition of weight-based ribavirin to Technivie therapy increased sustained virologic response after 12 weeks of daily therapy (SVR12) from 90% to 97% in patients with HCV genotype 1a and 90.9% to 100% in HCV genotype 4 patients . Zepatier therapy along with ribavirin improved SVR in HCV genotype 5 patients. Combination therapy of ribavirin and results in the SVR of 44% in patients with genotype 1 infection and 70% in patients with genotype 2-6. The inclusion of ribavirin in the combination therapies depend on individual patient's profile, for example if HCV genotype 3 patient has a Y93H genetic variant and compensated cirrhosis.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-beta-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide	ChEBI
1-beta-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide	ChEBI
RBV	ChEBI
Ribavirina	ChEBI
Ribavirine	ChEBI
Ribavirinum	ChEBI
Copegus	Kegg
Rebetol	Kegg
Ribasphere	Kegg
Virazole	Kegg
1-b-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide	Generator
1-Β-D-ribofuranosyl-1,2,4-triazole-3-carboxamide	Generator
1-b-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide	Generator
1-Β-D-ribofuranosyl-1H-1,2,4-triazole-3-carboxamide	Generator
Vilona	HMDB
ICN brand OF ribavirin	HMDB
Ribamide	HMDB
Ribamidyl	HMDB
Ribavirin merck brand	HMDB
Virazide	HMDB
Grossman brand OF ribavirin	HMDB
Merck brand OF ribavirin	HMDB
Pfizer brand OF ribavirin	HMDB
Ribovirin	HMDB
Three rivers pharmaceuticals brand OF ribavirin	HMDB
Dermatech brand OF ribavirin	HMDB
Essex brand OF ribavirin	HMDB
Ribamidil	HMDB
Tribavirin	HMDB
Viramide	HMDB

Chemical Formula

C₈H₁₂N₄O₅

Average Molecular Mass

244.205 g/mol

Monoisotopic Mass

244.081 g/mol

CAS Registry Number

36791-04-5

IUPAC Name

1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide

Traditional Name

ribavirin

SMILES

NC(=O)C1=NN(C=N1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

InChI Identifier

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

InChI Key

IWUCXVSUMQZMFG-AFCXAGJDSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as triazole ribonucleosides and ribonucleotides. These are nucleoside derivatives containing a ribose (or deoxyribose) moiety which is N-glycosylated to a triazole. Nucleotides have a phosphate group linked to the C5 carbon of the ribose (or deoxyribose) moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Triazole ribonucleosides and ribonucleotides

Sub Class

Not Available

Direct Parent

Triazole ribonucleosides and ribonucleotides

Alternative Parents

Substituents

N-ribosyl-1,2,4-triazole
Glycosyl compound
N-glycosyl compound
Pentose monosaccharide
2-heteroaryl carboxamide
Monosaccharide
Azole
Tetrahydrofuran
Triazole
1,2,4-triazole
Heteroaromatic compound
Carboxamide group
Secondary alcohol
Primary carboxylic acid amide
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Alcohol
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:63580 )
aromatic amide (CHEBI:63580 )
1-ribosyltriazole (CHEBI:63580 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	33.2 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-2.8	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	11.88	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	143.72 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	64.57 m³·mol⁻¹	ChemAxon
Polarizability	22.18 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-08nc-9320000000-385cc2e08cf140e0ecee	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0zpj-6922200000-75bb1d484addd27068ee	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-03di-0900000000-92e2bd11ded2c95f3fbd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-03di-0900000000-109ebb69f722bb3a92d7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-03di-2900000000-c0d63d0633c304d466ca	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-03xr-5900000000-c6f13aea6e263f2557f4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-02t9-9500000000-cefa4afc53cf92b724c3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-014i-9200000000-3a87882b304f3a9c9995	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-0900000000-d5e98a470d0e674937d2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-0900000000-c659efd26af31b3b98dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-1900000000-56c00c62af197ae8eecb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-2900000000-aa387f940aedc4b69874	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-03di-3900000000-795b88d3d651082dccb4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-02t9-9500000000-2ad23cf2e8f500d101cc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-6a9ceaf94e48a5856e63	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-18802a19d16454483630	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-014i-9200000000-f26697f5224329016008	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-03di-3900000000-03e82b27fd25878e95dc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-85ef00069e1dea09445a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-03di-3900000000-ec554c2067df2f7a90a5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-014l-9000000000-ab534ce4a5c6314c7208	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dj-1960000000-8e1936b4490afdea1b45	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-3900000000-34acc3537097bf33c4ec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ot-9400000000-9e7ebf6d4e248ffbf3bb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-2900000000-1aad1437a8d8217dea0e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-3900000000-0e379b4cf22b87e29955	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-0c0a02c5d745eb2131d7	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum