ChemFOnt: Showing chemical card for Ribavirin (CFc000009273)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:21 UTC

Chemfont ID

CFc000009273

Molecule Identification

Common Name

Ribavirin

Definition

Ribavirin is only found in individuals that have used or taken this drug. It is a nucleoside antimetabolite antiviral agent that blocks nucleic acid synthesis and is used against both RNA and DNA viruses. [PubChem]Ribavirin is readily phosphorylated intracellularly by adenosine kinase to ribavirin mono-, di-, and triphosphate metabolites. Ribavirin triphosphate (RTP) is a potent competitive inhibitor of inosine monophosphate (IMP) dehydrogenase, viral RNA polymerase and messenger RNA (mRNA) guanylyltransferase (viral) and can be incorporated into RNA in RNA viral species. Guanylyltranserase inhibition stops the capping of mRNA. These diverse effects result in a marked reduction of intracellular guanosine triphosphate (GTP) pools and inhibition of viral RNA and protein synthesis. Ribavirin is also incorporated into the viral genome causing lethal mutagenesis and a subsequent decrease in specific viral infectivity.

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 Weight

244.2047

Monoisotopic Molecular Weight

244.080769514

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

CAS Registry Number

36791-04-5

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 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014949)
Membrane (HMDB: HMDB0014949)

Source

Exogenous

Exogenous (HMDB: HMDB0014949)

Process

Not Available

Role

Not Available

Physical Properties

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0014949

DrugBank ID

DB00811

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

34439

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ribavirin

METLIN ID

Not Available

PubChem Compound

37542

PDB ID

Not Available

ChEBI ID

63580

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Ribavirin (CFc000009273)

MOL for CFc000009273 (Ribavirin)

3D MOL for CFc000009273 (Ribavirin)

3D SDF for CFc000009273 (Ribavirin)

3D-SDF for CFc000009273 (Ribavirin)

PDB for CFc000009273 (Ribavirin)

3D PDB for CFc000009273 (Ribavirin)

SMILES for CFc000009273 (Ribavirin)

INCHI for CFc000009273 (Ribavirin)

Structure for CFc000009273 (Ribavirin)

3D Structure for CFc000009273 (Ribavirin)