Taribavirin

Taribavirin

Clinical data
Other names	1-(β-D-Ribofuranosyl)- 1,2,4-triazole-3-carboximide
Pregnancy category	X
Routes of administration	Oral capsules)
ATC code	J05AB04 (WHO)
Legal status
Legal status	In Phase III drug trials
Pharmacokinetic data
Bioavailability	9%
Metabolism	Metabolized to 5'phosphates, de-riboside, and deriboside carboxylic acid
Elimination half-life	12 days - Multiple Dose; 120-170 hours - Single Dose
Excretion	10% fecal, remainder in urine (30% unchanged, remainder metabolites)
Identifiers
IUPAC name 1-[(2R,3R,4S,5R)- 3,4-dihydroxy-5- (hydroxymethyl)oxolan-2-yl]- 1,2,4-triazole-3-carboximidamide
JSmol)	Interactive image
SMILES n1c(nn(c1)[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO)C(=[N@H])N
InChI InChI=1S/C8H13N5O4/c9-6(10)7-11-2-13(12-7)8-5(16)4(15)3(1-14)17-8/h2-5,8,14-16H,1H2,(H3,9,10)/t3-,4-,5-,8-/m1/s1 Y Key:NHKZSTHOYNWEEZ-AFCXAGJDSA-N Y
NY (what is this?)  (verify)

Taribavirin (

Taribavirin is as active against influenza as ribavirin in animal models, with slightly less toxicity, so it may also eventually replace ribavirin as an anti-influenza agent.^{[citation needed]}

History

Taribavirin was first reported in 1973 by J. T. Witkowski et al.,

Note on formulas: The carboxamidine group of this molecule is somewhat basic, and therefore this drug is also known and administered as the hydrochloride salt (with a corresponding HCl chemical formula and different ChemID / PubChem number). At physiologic pH, the positive charge on the molecule from partial protonation of the carboximide group contributes to the relative slowness with which the drug crosses cell membranes (such as in red blood cells) until it has been metabolized into ribavirin. In the liver, however, the transformation from carboxamidine to carboxamide happens on first-pass metabolism and contributes to the higher levels of ribavirin found in liver cells and bile when viramidine is administered.^{[citation needed]}

Notes

References

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1. Barnard D (November 2002). "Viramidine (Ribapharm)". Current Opinion in Investigational Drugs. 3 (11): 1585–9.
   PMID 12476957
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2. Gish RG (January 2006). "Treating HCV with ribavirin analogues and ribavirin-like molecules". The Journal of Antimicrobial Chemotherapy. 57 (1): 8–13.
   PMID 16293677
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3. Lin CC, Luu K, Lourenco D, Yeh LT (August 2003). "Pharmacokinetics and metabolism of [14C]viramidine in rats and cynomolgus monkeys". Antimicrobial Agents and Chemotherapy. 47 (8): 2458–63.
   PMID 12878505
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4. Sidwell RW, Bailey KW, Wong MH, Barnard DL, Smee DF (October 2005). "In vitro and in vivo influenza virus-inhibitory effects of viramidine". Antiviral Research. 68 (1): 10–7.
   PMID 16087250
   .
5. Witkowski JT, Robins RK, Khare GP, Sidwell RW (August 1973). "Synthesis and antiviral activity of 1,2,4-triazole-3-thiocarboxamide and 1,2,4-triazole-3-carboxamidine ribonucleosides". Journal of Medicinal Chemistry. 16 (8): 935–7.
   PMID 4355593
   .