Compound: ribavirin
SMILES: O=C(N)c1nn([C@@H]2O[C@H](CO)[C@H]([C@H]2O)O)cn1
InChIKey: IWUCXVSUMQZMFG-AFCXAGJDSA-N
Synonyms: ribavirin, 36791-04-5, Tribavirin, Rebetol, Virazole, Copegus, Vilona, Ribamidil, Ribasphere, Ribavirine, Viramid, RTCA, Ribavirina, Varazid, Ribavirinum, Cotronak, 1-beta-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide, ICN-1229, Virazid, Ribavirin Mylan, Ribavirin Teva, 1-beta-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide, Ribavirin BioPartners, SCH 18908, DTXSID8023557, 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide, Ribavirin Teva Pharma B.V., NSC-163039, 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-1,2,4-triazole-3-carboxamide, CHEBI:63580, 49717AWG6K, ribofluranosyl carboxamide, 1H-1,2,4-Triazole-3-carboxamide, 1-beta-D-ribofuranosyl-, SCH-18908, DTXCID603557, Ribovirin, Viramide, NSC 163039, NSC163039, Ribavarin, ICN 1229, Ribapak, ICN1229, 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, RefChem:6200, J05AP01, 1-Beta-D-ribofuranosyl-1,2,4-triazolo-3-carboxamide, 1-beta-d-ribofuranosyl-1h-1,2, 4-triazole-3-carboxamide, 636-825-3, Ribamide, Ribavirine [INN-French], Ribavirinum [INN-Latin], Ribavirina [INN-Spanish], MFCD00058564, 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-1,2,4-triazole-3-carboxamide, RBV, Ribamidyl, Rebetron, Ribavirin Capsules, 1-(beta-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxamide, Rebretron, Virazide, 1H-1,2,4-Triazole-3-carboxamide, 1-.beta.-D-ribofuranosyl-, Ribav, 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-1,2,4-triazole-3-carboxamide, 1-ss-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide, RTC, Ravanex, Ribacine, C-Virin, DRG-0028, Ribasphere (TN), Virazole (TN), SMR000058315, Copegus (TN), Rebetol (TN), HSDB 6513, SR-01000076112, BRN 0892462, Ribavirvin, UNII-49717AWG6K, VirustazCotronak, Tribavirin;, Ribamidil;, Virazide;, Virazole;, s2504, Viramid;, Viratek;, Virazid;, Ribavirin CRS, Vilona;, Ribavirin [USAN:USP:INN:BAN], NCGC00015904-02, 66510-90-5, Ribavirin, antiviral, CAS-36791-04-5, RG-964, Ribavirin (Copegus), Ribavirin (Standard), Ribavirin (Copegus)?, Ro-20-9963, Spectrum_001826, 4pb1, RIBAVIRIN [INN], RIBAVIRIN [JAN], RIBAVIRIN [MI], RIBAVIRIN [HSDB], RIBAVIRIN [USAN], Prestwick3_000993, Spectrum3_001876, Spectrum4_001252, Spectrum5_002075, RIBAVIRIN [VANDF], R-964, Epitope ID:768752, RIBAVIRIN [MART.], R 9644, RIBAVIRIN [USP-RS], RIBAVIRIN [WHO-DD], SCHEMBL3727, 1-.beta.-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide, CHEMBL1643, Lopac0_001063, BSPBio_001085, BSPBio_003352, KBioGR_001804, KBioSS_002331, RIBAVIRIN [EMA EPAR], AA-504/07617051, cid_37542, MLS000028486, MLS002222317, DivK1c_000782, SPECTRUM1503938, Ribavirin (JP18/USP/INN), BPBio1_001195, GTPL6842, orb1310388, orb3140076, RIBAVIRIN [ORANGE BOOK], 1,2,4-Triazole-3-carboxamide, 1-beta-D-ribofuranosyl-, 1-.beta.-D-Ribofuranosyl-1,2,4-triazolo-3-carboxamide, RIBAVIRIN [EP MONOGRAPH], HMS502H04, HY-B0434R, KBio1_000782, KBio2_002328, KBio2_004896, KBio2_007464, KBio3_002854, RIBAVIRIN [USP MONOGRAPH], NINDS_000782, GLXC-05861, HMS2090L15, HMS2094O09, HMS2098G07, HMS2232P07, HMS3263E08, HMS3715G07, Pharmakon1600-01503938, ALBB-038667, HY-B0434, MSK10023, Tox21_110259, Tox21_200967, Tox21_501063, BDBM50154375, CCG-38985, EBC-00633, HB4522, NSC758650, AKOS001715163, Tox21_110259_1, DB00811, GS-3572, LP01063, NR02712, NSC-758650, SDCCGSBI-0051033.P004, IDI1_000782, SMP1_000261, NCGC00090726-01, NCGC00090726-03, NCGC00090726-04, NCGC00090726-05, NCGC00090726-06, NCGC00090726-07, NCGC00090726-08, NCGC00090726-09, NCGC00090726-12, NCGC00090726-25, NCGC00090726-30, NCGC00258520-01, NCGC00261748-01, 252269-50-4, AS-34178, SY055294, SBI-0051033.P003, AB00430481, EU-0101063, NS00009126, R0077, EN300-59237, D00423, AB00430481-15, AB00430481-16, AB00430481_17, AB00430481_18, Ribavirin, Antibiotic for Culture Media Use Only, 1-beta-Ribofuranosyl-1,2,4-triazole-3-carboamide, F079125, Q421862, Ribavirin 100 microg/mL in Acetonitrile:Methanol, SR-01000721904, 1-b-d-ribofuranosyl-1,2,4-triazole-3-carboxamide, Q-201670, SR-01000076112-2, SR-01000076112-3, SR-01000076112-4, SR-01000721904-2, BRD-K60369935-001-02-7, BRD-K60369935-001-15-9, BRD-K60369935-001-18-3, SR-01000076112-11, 1-(beta-D-Ribofuranosyl)-1,2,4-triazole-3-carboxamide, 1-|_-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide, 1-|A-D-Ribofuranosyl-1H-1,2,4-triazole-3-carboxamide, Ribavirin, British Pharmacopoeia (BP) Reference Standard, Z594284196, 1-(beta -D-ribofuranosyl)-1,2,4-triazole-3-carboxamide, Ribavirin, European Pharmacopoeia (EP) Reference Standard, Ribavirin, United States Pharmacopeia (USP) Reference Standard, Ribavirin, Pharmaceutical Secondary Standard; Certified Reference Material, 1-[(2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide; 1-?-D-Ribofuranosyl-1,2,4-triazole-3-carboxamide
Theoretical properties:
molecular_formula: C8H12N4O5
molecular_weight: 244.20 g/mol
exact_mass: 244.08076950 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 3
heavy_atom_count: 17
topological_polar_surface_area: 144 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Colorless
color: Colorless
odor: Odorless
melting_point: 345 to 349 °F (NTP, 1992)
solubility: greater than or equal to 100 mg/mL at 66 °F (NTP, 1992)
Descriptions:
pubchem: Ribavirin can cause developmental toxicity and male reproductive toxicity according to state or federal government labeling requirements.
chebi: A 1-ribosyltriazole that is the 1-ribofuranosyl derivative of 1,2,4-triazole-3-carboxamide. A synthetic guanosine analogue, it is an inhibitor of HCV polymerase and possesses a broad spectrum of activity against DNA and RNA viruses.
chembl: RIBAVIRIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Ribavirin, also known as tribavirin, is an antiviral medication used to treat illness caused by respiratory syncytial virus (RSV) and hepatitis C virus (HCV) infections, as well as some viral hemorrhagic fevers. For HCV, it is used in combination with other medications, such as simeprevir, sofosbuvir, peginterferon alfa-2b or peginterferon alfa-2a. It can also be used for viral hemorrhagic fevers—specifically, for Lassa fever, Crimean–Congo hemorrhagic fever, and Hantavirus infections (with exceptions for Ebola or Marburg virus diseases). Ribavirin is usually taken orally (by mouth) or inhaled. Despite widespread usage, it has faced scrutiny in the 21st century because of lack of proven efficacy in treating viral infections for which it has been prescribed in the past.
Its common side effects include fatigue, headache, nausea, fever, muscle pains, and an irritable mood. Serious side effects include red blood cell breakdown, liver problems, and allergic reactions. Its use during pregnancy can bring harm to the developing fetus. Effective birth control is recommended for both males and females for at least seven months during and after use. The mechanism of action of ribavirin is not entirely clear.
Ribavirin was patented in 1971 and approved for medical use in 1986. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.