Voxilaprevir: Difference between revisions

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{{short description|Protease inhibitor}}
{{Use dmy dates|date=January 2020}}
{{Infobox drug
{{Infobox drug
| drug_name =
| IUPAC_name =
| type =
⚫
| image = Voxilaprevir.svg
| IUPAC_name = (1''R'',18''R'',20''R'',24''S'',27''S'',28''S'')-''N''-[(1''R'',2''R'')-2-(Difluoromethyl)-1-<nowiki>{[(</nowiki>1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]-28-ethyl-13,13-difluoro-7-methoxy-24-(2-methyl-2-propanyl)-22,25-dioxo-2,21-dioxa-4,11,23,26-tetraazapentacyclo[24.2.1.0<sup>3,12</sup>.0<sup>5,10</sup>.0<sup>18,20</sup>]nonacosa-3(12),4,6,8,10-pentaene-27-carboxamide
| alt =
⚫
| image = Voxilaprevir.svg
⚫
| caption =
| alt =
⚫
| caption =
<!-- Clinical data -->
<!-- Clinical data -->
| pronounce =
| pronounce =
| tradename = Vosevi (combination with [[sofosbuvir]] and [[velpatasvir]])
| tradename = Vosevi (combination with [[sofosbuvir]] and [[velpatasvir]])
| Drugs.com =
| Drugs.com =
| MedlinePlus =
| MedlinePlus =
| licence_EU =
⚫
| pregnancy_AU = <!-- A/B1/B2/B3/C/D/X -->
| licence_US =
⚫
| pregnancy_AU_comment =
| pregnancy_US = <!-- A/B/C/D/X/N -->
| pregnancy_AU = <!-- A/B1/B2/B3/C/D/X -->
⚫
| pregnancy_AU_comment =
⚫
| pregnancy_category=
⚫
| pregnancy_US = <!-- A/B/C/D/X/N -->
⚫
| routes_of_administration =
⚫
| pregnancy_category =
⚫
| routes_of_administration =
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_AU_comment =
| legal_AU_comment =
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| legal_US = <!-- OTC/Rx-only/Schedule I, II, III, IV, V -->
| legal_US = <!-- OTC/Rx-only/Schedule I, II, III, IV, V -->
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_status = <!-- Free text -->
| legal_status = <!-- Free text -->
<!-- Pharmacokinetic data -->
<!-- Pharmacokinetic data -->
| bioavailability =
| bioavailability =
| protein_bound =
| protein_bound =
| metabolism =
| metabolism =
| metabolites =
| metabolites =
| onset =
| onset =
| elimination_half-life =
| elimination_half-life =
| duration_of_action =
| duration_of_action =
| excretion =
| excretion =
<!-- Identifiers -->
<!-- Identifiers -->
| CAS_number = 1535212-07-7
| CAS_number = 1535212-07-7
| PDB_ligand = L9P
| class =
| class =
| ATCvet =
| ATCvet =
| ATC_prefix = <!-- 'none' if uncategorised -->
| ATC_prefix = <!-- 'none' if uncategorised -->
| ATC_suffix =
| ATC_suffix =
| PubChem = 89921642
| PubChem = 89921642
| DrugBank =
| DrugBank =
| ChemSpiderID = 44209500
| ChemSpiderID = 44209500
| UNII = 0570F37359
| UNII = 0570F37359
| KEGG = D10899
<!-- Chemical and physical data -->
<!-- Chemical and physical data -->
⚫
| C = 40 | H = 52 | F = 4 | N = 6 | O = 9 | S = 1
| chemical_formula =
⚫
| C=40 | H=52 | F=4 | N=6 | O=9 | S=1
| molecular_weight =
| smiles = CC[C@@H]1[C@@H]2CN([C@@H]1C(=O)N[C@@]3(C[C@H]3C(F)F)C(=O)NS(=O)(=O)C4(CC4)C)C(=O)[C@@H](NC(=O)O[C@@H]5C[C@H]5CCCCC(c6c(nc7cc(ccc7n6)OC)O2)(F)F)C(C)(C)C
| smiles = CC[C@@H]1[C@@H]2CN([C@@H]1C(=O)N[C@@]3(C[C@H]3C(F)F)C(=O)NS(=O)(=O)C4(CC4)C)C(=O)[C@@H](NC(=O)O[C@@H]5C[C@H]5CCCCC(c6c(nc7cc(ccc7n6)OC)O2)(F)F)C(C)(C)C
| StdInChI=1S/C40H52F4N6O9S/c1-7-22-27-19-50(28(22)32(51)48-39(18-23(39)31(41)42)35(53)49-60(55,56)38(5)14-15-38)34(52)30(37(2,3)4)47-36(54)59-26-16-20(26)10-8-9-13-40(43,44)29-33(58-27)46-25-17-21(57-6)11-12-24(25)45-29/h11-12,17,20,22-23,26-28,30-31H,7-10,13-16,18-19H2,1-6H3,(H,47,54)(H,48,51)(H,49,53)/t20-,22-,23+,26-,27+,28+,30-,39-/m1/s1
| StdInChI = 1S/C40H52F4N6O9S/c1-7-22-27-19-50(28(22)32(51)48-39(18-23(39)31(41)42)35(53)49-60(55,56)38(5)14-15-38)34(52)30(37(2,3)4)47-36(54)59-26-16-20(26)10-8-9-13-40(43,44)29-33(58-27)46-25-17-21(57-6)11-12-24(25)45-29/h11-12,17,20,22-23,26-28,30-31H,7-10,13-16,18-19H2,1-6H3,(H,47,54)(H,48,51)(H,49,53)/t20-,22-,23+,26-,27+,28+,30-,39-/m1/s1
| StdInChIKey = MZBLZLWXUBZHSL-FZNJKFJKSA-N
| StdInChIKey = MZBLZLWXUBZHSL-FZNJKFJKSA-N
| density = 1.4±0.1<ref name="chemsrc">{{Cite web|url=https://www.chemsrc.com/en/cas/1535212-07-7_1287459.html|title=voxilaprevir_msds}}</ref>
| Jmol=None
}}
}}


'''Voxilaprevir''' is a [[hepatitis C virus]] (HCV) nonstructural (NS) protein [[NS3 (HCV)|3]]/[[NS4A|4A]] protease inhibitor that is used in combination with [[sofosbuvir]] and [[velpatasvir]]. The combination has the trade name ''Vosevi'' and has received a positive opinion from the European [[Committee for Medicinal Products for Human Use]] in June 2017.<ref>{{cite web|url=http://www.ema.europa.eu/docs/en_GB/document_library/Summary_of_opinion_-_Initial_authorisation/human/004350/WC500229884.pdf|publisher=[[European Medicines Agency]]|title=Summary of opinion: Vosevi|date=22 June 2017}}</ref>
'''Voxilaprevir''' is a [[hepatitis C virus]] (HCV) nonstructural (NS) protein [[NS3 (HCV)|3]]/[[NS4A|4A]] protease inhibitor (by [[Gilead Sciences|Gilead]]) that is used in combination with [[sofosbuvir]] and [[velpatasvir]].<ref name="Heo_2018">{{cite journal | vauthors = Heo YA, Deeks ED | title = Sofosbuvir/Velpatasvir/Voxilaprevir: A Review in Chronic Hepatitis C | journal = Drugs | volume = 78 | issue = 5 | pages = 577–587 | date = April 2018 | pmid = 29546556 | doi = 10.1007/s40265-018-0895-5 | s2cid = 4395880 }}</ref> The combination has the trade name [[Vosevi]] and received a positive opinion from the European [[Committee for Medicinal Products for Human Use]] in June 2017.<ref>{{cite web|url=http://www.ema.europa.eu/docs/en_GB/document_library/Summary_of_opinion_-_Initial_authorisation/human/004350/WC500229884.pdf|publisher=[[European Medicines Agency]]|title=Summary of opinion: Vosevi|date=22 June 2017}}</ref>

On 18 July 2017, Vosevi was approved by the US [[Food and Drug Administration]].<ref>[https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm567467.htm FDA approves Vosevi for Hepatitis C]</ref>


==References==
==References==
{{reflist}}
{{Reflist}}

{{RNA antivirals}}

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[[Category:NS3/4A protease inhibitors]]
[[Category:NS3/4A protease inhibitors]]
[[Category:Tert-butyl compounds]]




Latest revision as of 16:37, 28 January 2023

Voxilaprevir
Clinical data
Trade namesVosevi (combination with sofosbuvir and velpatasvir)
Identifiers
  • (1R,18R,20R,24S,27S,28S)-N-[(1R,2R)-2-(Difluoromethyl)-1-{[(1-methylcyclopropyl)sulfonyl]carbamoyl}cyclopropyl]-28-ethyl-13,13-difluoro-7-methoxy-24-(2-methyl-2-propanyl)-22,25-dioxo-2,21-dioxa-4,11,23,26-tetraazapentacyclo[24.2.1.03,12.05,10.018,20]nonacosa-3(12),4,6,8,10-pentaene-27-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
PDB ligand
Chemical and physical data
FormulaC40H52F4N6O9S
Molar mass868.94 g·mol−1
3D model (JSmol)
Density1.4±0.1[1] g/cm3
  • CC[C@@H]1[C@@H]2CN([C@@H]1C(=O)N[C@@]3(C[C@H]3C(F)F)C(=O)NS(=O)(=O)C4(CC4)C)C(=O)[C@@H](NC(=O)O[C@@H]5C[C@H]5CCCCC(c6c(nc7cc(ccc7n6)OC)O2)(F)F)C(C)(C)C
  • InChI=1S/C40H52F4N6O9S/c1-7-22-27-19-50(28(22)32(51)48-39(18-23(39)31(41)42)35(53)49-60(55,56)38(5)14-15-38)34(52)30(37(2,3)4)47-36(54)59-26-16-20(26)10-8-9-13-40(43,44)29-33(58-27)46-25-17-21(57-6)11-12-24(25)45-29/h11-12,17,20,22-23,26-28,30-31H,7-10,13-16,18-19H2,1-6H3,(H,47,54)(H,48,51)(H,49,53)/t20-,22-,23+,26-,27+,28+,30-,39-/m1/s1
  • Key:MZBLZLWXUBZHSL-FZNJKFJKSA-N

Voxilaprevir is a hepatitis C virus (HCV) nonstructural (NS) protein 3/4A protease inhibitor (by Gilead) that is used in combination with sofosbuvir and velpatasvir.[2] The combination has the trade name Vosevi and received a positive opinion from the European Committee for Medicinal Products for Human Use in June 2017.[3]

On 18 July 2017, Vosevi was approved by the US Food and Drug Administration.[4]

References[edit]

  1. ^ "voxilaprevir_msds".
  2. ^ Heo YA, Deeks ED (April 2018). "Sofosbuvir/Velpatasvir/Voxilaprevir: A Review in Chronic Hepatitis C". Drugs. 78 (5): 577–587. doi:10.1007/s40265-018-0895-5. PMID 29546556. S2CID 4395880.
  3. ^ "Summary of opinion: Vosevi" (PDF). European Medicines Agency. 22 June 2017.
  4. ^ FDA approves Vosevi for Hepatitis C


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