SETROBUVIR

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H25FN4O6S2
Molecular Weight	560.618
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12[C@@H]3CC[C@@H](C3)[C@@]1([H])C(O)=C(C(=O)N2CC4=CC=C(F)C=C4)C5=NS(=O)(=O)C6=CC(NS(C)(=O)=O)=CC=C6N5

InChI

InChIKey=DEKOYVOWOVJMPM-RLHIPHHXSA-N

InChI=1S/C25H25FN4O6S2/c1-37(33,34)28-17-8-9-18-19(11-17)38(35,36)29-24(27-18)21-23(31)20-14-4-5-15(10-14)22(20)30(25(21)32)12-13-2-6-16(26)7-3-13/h2-3,6-9,11,14-15,20,22,28,31H,4-5,10,12H2,1H3,(H,27,29)/t14-,15+,20+,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C25H25FN4O6S2
Molecular Weight	560.618
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29317572 | https://adisinsight.springer.com/drugs/800014226

Setrobuvir (also known as ANA-598 and RG7790) is an orally administered, small-molecule non-nucleoside polymerase inhibitor, which was in development by Roche company. Setrobuvir has been used in trials studying the treatment of chronic hepatitis C. Setrobuvir is a non–nucleoside NS5B inhibitor (NNI). It has shown potency and a high degree of specificity against HCV genotype 1 NS5B polymerase, leading to 73% SVR when orally administrated to patients in combination with pegylated interferon and ribavirin. An interferon-free setrobuvir based regimes of three direct acting antivirals (DAAs) plus ribavirin has also been shown to be safe and effective in genotype 1 treatment naive patients.

Originator

Approval Year

PubMed

Title	Date	PubMed
Pharmacokinetics and pharmacodynamics of setrobuvir, an orally administered hepatitis C virus non-nucleoside analogue inhibitor.	2014 Dec 1	25456558
Interferon-free regimens containing setrobuvir for patients with genotype 1 chronic hepatitis C: a randomized, multicenter study.	2016 Apr	26519669
A pharmacokinetic/viral kinetic model to evaluate treatment of chronic HCV infection with a non-nucleoside polymerase inhibitor.	2018	29317572

Patents

Sample Use Guides

In Vivo Use Guide

Three studies investigated the pharmacokinetics and pharmacodynamics of setrobuvir. First, sequential cohorts of volunteers were randomly assigned to receive single oral doses of setrobuvir 400 to 3000 mg or placebo in a double-blind, ascending dose study. In the second study, volunteers were randomly assigned to receive multiple doses of setrobuvir (400 or 800 mg once daily [QD] or 600 mg twice a day [BID]). In the third study, patients with genotype 1 CHC received setrobuvir (200, 400, or 800 mg) or placebo BID for 3 days. Pharmacokinetics of setrobuvir appear to be dose proportional, and setrobuvir produces a mean reduction of 2.9 log10 IU/mL in HCV RNA over 3 days in patients with genotype 1 (a and b) treated with 800 mg BID.

Route of Administration: Oral

In Vitro Use Guide

44% ± 14.6% inhibition of G2a replicon replication was observed with the maximal concentration of 100 uM (>12,000-fold increase in EC50) for Setrobuvir. Setrobuvir inhibited the replication of the G1b replicon with an EC50 of 8.1 nM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 20:15:49 UTC 2023` Edited by `admin` on `Fri Dec 15 20:15:49 UTC 2023`
Record UNII	T5B2GI8F84
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SETROBUVIR

Official Name

English

METHANESULFONAMIDE, N-(3-((4AR,5S,8R,8AS)-1,2,4A,5,6,7,8,8A-OCTAHYDRO-4-HYDROXY-2-OXO-5,8-METHANOQUINOLIN-3-YL)-1,1-DIOXIDO-2H-1,2,4-BENZOTHIADIAZIN-7-YL)-

Systematic Name

English

RO-5466731

Code

English

ANA598

Code

English

SETROBUVIR [USAN]

Common Name

English

ANA-598

Code

English

Setrobuvir [WHO-DD]

Common Name

English

setrobuvir [INN]

Common Name

English

RO5466731

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C281