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{{Short description|Compound}}
{{Use dmy dates|date=November 2023}}
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{Chembox
{{Chembox
| ImageFile = Asunaprevir.svg
| ImageFile = Asunaprevir.svg
| IUPACName = 3-Methyl-''N''-{[(2-methyl-2-propanyl)oxy]carbonyl}-<small>L</small>-valyl-(4''R'')-4-[(7-chloro-4-methoxy-1-isoquinolinyl)oxy]-''N''-{(1''R'',2''S'')-1-[(cyclopropylsulfonyl)carbamoyl]-2-vinylcyclopropyl}-<small>L</small>-prolinamide
| IUPACName = 3-Methyl-''N''-{[(2-methyl-2-propanyl)oxy]carbonyl}-<small>L</small>-valyl-(4''R'')-4-[(7-chloro-4-methoxy-1-isoquinolinyl)oxy]-''N''-{(1''R'',2''S'')-1-[(cyclopropylsulfonyl)carbamoyl]-2-vinylcyclopropyl}-<small>L</small>-prolinamide
| PIN = ''tert''-Butyl {(2''S'')-1-[(3<sup>2</sup>''S'',3<sup>4</sup>''R'',6<sup>1</sup>''R'',6<sup>2</sup>''S'')-1<sup>7</sup>-chloro-6<sup>2</sup>-ethenyl-1<sup>4</sup>-methoxy-4,7,9,9-tetraoxo-2-oxa-9λ<sup>6</sup>-thia-5,8-diaza-1(1)-isoquinolina-3(4,2)-pyrrolidina-6(1,1),10(1)-dicyclopropadecaphan-3<sup>1</sup>-yl]-3,3-dimethyl-1-oxobutan-2-yl}carbamate
| SystematicName = ''tert''-Butyl {(2''S'')-1-[(3<sup>2</sup>''S'',3<sup>4</sup>''R'',6<sup>1</sup>''R'',6<sup>2</sup>''S'')-1<sup>7</sup>-chloro-6<sup>2</sup>-ethenyl-1<sup>4</sup>-methoxy-4,7,9,9-tetraoxo-2-oxa-9λ<sup>6</sup>-thia-5,8-diaza-1(1)-isoquinolina-3(4,2)-pyrrolidina-6(1,1),10(1)-dicyclopropadecaphan-3<sup>1</sup>-yl]-3,3-dimethyl-1-oxobutan-2-yl}carbamate
| OtherNames = BMS-650032
| OtherNames = BMS-650032
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
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| PubChem = 16076883
| PubChem = 16076883
| ChemSpiderID = 17235944
| ChemSpiderID = 17235944
| ChEBI = 134723
| DrugBank = DB11586
| IUPHAR_ligand = 10882
| ChEMBL = 2105735
| ChEMBL = 2105735
| KEGG = D10093
| KEGG = D10093
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| Solubility =
| Solubility =
}}
}}
|Section6={{Chembox Pharmacology
| Section6 = {{Chembox Pharmacology
| Pharmacology_ref =
| ATCCode_prefix = J05
| ATCCode_prefix = J05
| ATCCode_suffix = AP06
| ATCCode_suffix = AP06
| ATC_Supplemental =
⚫
}}
| ATCvet =
| Licence_EU =
| INN =
| INN_EMA =
| Licence_US =
| Legal_status =
| Legal_AU = S4
| Legal_AU_comment = <ref>{{cite web | title=Prescription medicines: registration of new chemical entities in Australia, 2015 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/prescription-medicines-registration-new-chemical-entities-australia-2015 | access-date=10 April 2023}}</ref>
| Legal_CA = Rx-only
| Legal_CA_comment = <ref>{{cite web | title=Health Canada New Drug Authorizations: 2016 Highlights | website=[[Health Canada]] | date=14 March 2017 | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/health-canada-new-drug-authorizations-2016-highlights.html | access-date=7 April 2024}}</ref>
| Legal_NZ =
| Legal_NZ_comment =
| Legal_UK =
| Legal_UK_comment =
| Legal_US =
| Legal_US_comment =
| Legal_EU =
| Legal_EU_comment =
| Legal_UN =
| Legal_UN_comment =
| Pregnancy_category =
| Pregnancy_AU =
| Pregnancy_AU_comment =
| Dependence_liability =
| AdminRoutes =
| Bioavail =
| ProteinBound =
| Metabolism =
| Metabolites =
| OnsetOfAction =
| HalfLife =
| DurationOfAction =
| Excretion =
⚫
}}
|Section7={{Chembox Hazards
|Section7={{Chembox Hazards
| MainHazards =
| MainHazards =
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}}
}}


'''Asunaprevir''' (formerly '''BMS-650032''', brand name in [[Japan]] and [[Russia]]<ref>{{cite web|title=Sunvepra™ (asunaprevir) soft gelatin capsules 100 mg. Registration certificate|url=http://grls.rosminzdrav.ru/Grls_View_v2.aspx?idReg=374742&t=|website=State Register of Medicines|accessdate=26 August 2015|language=Russian}}</ref> '''Sunvepra''') is an experimental drug candidate for the treatment of [[hepatitis C]]. It was undergoing [[drug development|development]] by [[Bristol-Myers Squibb]] and has completed [[Phase III clinical trials]] in 2013.<ref>{{cite web | url = http://clinicaltrials.gov/ct2/show/NCT01497834 | title = A Phase 3 Study in Combination With BMS-790052 and BMS-650032 in Japanese Hepatitis C Virus (HCV) Patients | date = 23 September 2015 | publisher = [[ClinicalTrials.gov]]}}</ref>
'''Asunaprevir''' (formerly '''BMS-650032''', brand name in [[Japan]] and [[Russia]]<ref>{{cite web|title=Sunvepra (asunaprevir) soft gelatin capsules 100 mg. Registration certificate|url=http://grls.rosminzdrav.ru/Grls_View_v2.aspx?idReg=374742&t=|website=State Register of Medicines|accessdate=26 August 2015|language=Russian}}</ref> '''Sunvepra''') is an experimental drug candidate for the treatment of [[hepatitis C]]. It was undergoing [[drug development|development]] by [[Bristol-Myers Squibb]] and has completed [[Phase III clinical trials]] in 2013.<ref>{{cite web | url = http://clinicaltrials.gov/ct2/show/NCT01497834 | title = A Phase 3 Study in Combination With BMS-790052 and BMS-650032 in Japanese Hepatitis C Virus (HCV) Patients | date = 23 September 2015 | publisher = [[ClinicalTrials.gov]]}}</ref>


Asunaprevir is an [[enzyme inhibitor|inhibitor]] of the [[hepatitis C virus]] enzyme [[NS3 (HCV)|serine protease NS3]].<ref>{{cite journal | title = Asunaprevir. HCV serine protein NS3 inhibitor, Treatment of hepatitis C virus | author = C. Reviriego | journal = Drugs of the Future | year = 2012 | volume = 37 | issue = 4 | pages = 247–254 | doi = 10.1358/dof.2012.037.04.1789350| url = https://journals.prous.com/journals/servlet/xmlxsl/pk_journals.xml_summary_pr?p_JournalId=2&p_RefId=1789350&p_IsPs=N}}</ref>
Asunaprevir is an [[enzyme inhibitor|inhibitor]] of the [[hepatitis C virus]] enzyme [[NS3 (HCV)|serine protease NS3]].<ref>{{cite journal | title = Asunaprevir. HCV serine protein NS3 inhibitor, Treatment of hepatitis C virus | author = C. Reviriego | journal = Drugs of the Future | year = 2012 | volume = 37 | issue = 4 | pages = 247–254 | doi = 10.1358/dof.2012.037.04.1789350| url = https://journals.prous.com/journals/servlet/xmlxsl/pk_journals.xml_summary_pr?p_JournalId=2&p_RefId=1789350&p_IsPs=N}}</ref> Asunaprevir is being tested in combination with [[pegylated interferon]] and [[ribavirin]], as well as in interferon-free regimens with other direct-acting antiviral agents including [[daclatasvir]].<ref>{{cite journal | vauthors = Lok AS, Gardiner DF, Lawitz E, Martorell C, Everson GT, Ghalib R, Reindollar R, Rustgi V, McPhee F, Wind-Rotolo M, Persson A, Zhu K, Dimitrova DI, Eley T, Guo T, Grasela DM, Pasquinelli C | title = Preliminary study of two antiviral agents for hepatitis C genotype 1 | journal = The New England Journal of Medicine | volume = 366 | issue = 3 | pages = 216–24 | date = January 2012 | pmid = 22256805 | doi = 10.1056/NEJMoa1104430 | doi-access = free }}</ref><ref>{{cite web | url = https://www.bloomberg.com/news/2012-04-19/bristol-myers-daclatasvir-asunaprevir-cured-77-study.html | title = Bristol-Myers' Daclatasvir, Asunaprevir Cured 77%: Study | publisher = [[Bloomberg L.P.|Bloomberg]] | date = Apr 19, 2012}}</ref><ref>[http://www.hivandhepatitis.com/hepatitis-c/hepatitis-c-topics/hcv-treatment/3337-aasld-daclatasvir-plus-asunaprevir-rapidly-suppresses-hcv-in-prior-null-responders AASLD: Daclatasvir plus Asunaprevir Rapidly Suppresses HCV in Prior Null Responders] {{Webarchive|url=https://web.archive.org/web/20150208163151/http://www.hivandhepatitis.com/hepatitis-c/hepatitis-c-topics/hcv-treatment/3337-aasld-daclatasvir-plus-asunaprevir-rapidly-suppresses-hcv-in-prior-null-responders |date=2015-02-08 }}. Highleyman, L. HIVandHepatitis.com. 8 November 2011.</ref>

Asunaprevir is being tested in combination with [[pegylated interferon]] and [[ribavirin]], as well as in interferon-free regimens with other direct-acting antiviral agents including [[daclatasvir]].<ref>{{cite journal | last1 = Lok | first1 = A | display-authors = etal | year = 2012 | title = Preliminary Study of Two Antiviral Agents for Hepatitis C Genotype 1 | journal = New England Journal of Medicine | volume = 366 | issue = 3| pages = 216–224 | doi=10.1056/NEJMoa1104430 | pmid = 22256805| doi-access = free }}</ref><ref>{{cite web | url = https://www.bloomberg.com/news/2012-04-19/bristol-myers-daclatasvir-asunaprevir-cured-77-study.html | title = Bristol-Myers' Daclatasvir, Asunaprevir Cured 77%: Study | publisher = [[Bloomberg L.P.|Bloomberg]] | date = Apr 19, 2012}}</ref><ref>[http://www.hivandhepatitis.com/hepatitis-c/hepatitis-c-topics/hcv-treatment/3337-aasld-daclatasvir-plus-asunaprevir-rapidly-suppresses-hcv-in-prior-null-responders AASLD: Daclatasvir plus Asunaprevir Rapidly Suppresses HCV in Prior Null Responders] {{Webarchive|url=https://web.archive.org/web/20150208163151/http://www.hivandhepatitis.com/hepatitis-c/hepatitis-c-topics/hcv-treatment/3337-aasld-daclatasvir-plus-asunaprevir-rapidly-suppresses-hcv-in-prior-null-responders |date=2015-02-08 }}. Highleyman, L. HIVandHepatitis.com. 8 November 2011.</ref>

==See also==
* [[Boceprevir]]
* [[Telaprevir]]


==References==
==References==
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[[Category:Cyclopropanes]]
[[Category:Cyclopropanes]]
[[Category:CYP2D6 inhibitors]]
[[Category:CYP2D6 inhibitors]]
[[Category:Experimental drugs]]
[[Category:Experimental antiviral drugs]]
[[Category:Isoquinolines]]
[[Category:Isoquinolines]]
[[Category:NS3/4A protease inhibitors]]
[[Category:NS3/4A protease inhibitors]]
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[[Category:Sulfonamides]]
[[Category:Sulfonamides]]
[[Category:Tert-butyl compounds]]
[[Category:Tert-butyl compounds]]
[[Category:Methoxy compounds]]



{{Antiinfective-drug-stub}}
{{Antiinfective-drug-stub}}

Revision as of 05:20, 7 April 2024

Asunaprevir
Names
IUPAC name
3-Methyl-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-valyl-(4R)-4-[(7-chloro-4-methoxy-1-isoquinolinyl)oxy]-N-{(1R,2S)-1-[(cyclopropylsulfonyl)carbamoyl]-2-vinylcyclopropyl}-L-prolinamide
Systematic IUPAC name
tert-Butyl {(2S)-1-[(32S,34R,61R,62S)-17-chloro-62-ethenyl-14-methoxy-4,7,9,9-tetraoxo-2-oxa-9λ6-thia-5,8-diaza-1(1)-isoquinolina-3(4,2)-pyrrolidina-6(1,1),10(1)-dicyclopropadecaphan-31-yl]-3,3-dimethyl-1-oxobutan-2-yl}carbamate
Other names
BMS-650032
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.206.482 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C35H46ClN5O9S/c1-9-19-16-35(19,31(44)40-51(46,47)22-11-12-22)39-28(42)25-15-21(49-29-24-14-20(36)10-13-23(24)26(48-8)17-37-29)18-41(25)30(43)27(33(2,3)4)38-32(45)50-34(5,6)7/h9-10,13-14,17,19,21-22,25,27H,1,11-12,15-16,18H2,2-8H3,(H,38,45)(H,39,42)(H,40,44)/t19-,21-,25+,27-,35-/m1/s1
    Key: XRWSZZJLZRKHHD-WVWIJVSJSA-N
  • InChI=1/C35H46ClN5O9S/c1-9-19-16-35(19,31(44)40-51(46,47)22-11-12-22)39-28(42)25-15-21(49-29-24-14-20(36)10-13-23(24)26(48-8)17-37-29)18-41(25)30(43)27(33(2,3)4)38-32(45)50-34(5,6)7/h9-10,13-14,17,19,21-22,25,27H,1,11-12,15-16,18H2,2-8H3,(H,38,45)(H,39,42)(H,40,44)/t19-,21-,25+,27-,35-/m1/s1
    Key: XRWSZZJLZRKHHD-WVWIJVSJBJ
  • O=C(N5[C@H](C(=O)N[C@@]2(C(=O)NS(=O)(=O)C1CC1)[C@H](\C=C)C2)C[C@@H](Oc3ncc(OC)c4c3cc(Cl)cc4)C5)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C
Properties
C35H46ClN5O9S
Molar mass 748.29 g·mol−1
Pharmacology
J05AP06 (WHO)
Legal status
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Asunaprevir (formerly BMS-650032, brand name in Japan and Russia[3] Sunvepra) is an experimental drug candidate for the treatment of hepatitis C. It was undergoing development by Bristol-Myers Squibb and has completed Phase III clinical trials in 2013.[4]

Asunaprevir is an inhibitor of the hepatitis C virus enzyme serine protease NS3.[5] Asunaprevir is being tested in combination with pegylated interferon and ribavirin, as well as in interferon-free regimens with other direct-acting antiviral agents including daclatasvir.[6][7][8]

References

  1. ^ "Prescription medicines: registration of new chemical entities in Australia, 2015". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.
  2. ^ "Health Canada New Drug Authorizations: 2016 Highlights". Health Canada. 14 March 2017. Retrieved 7 April 2024.
  3. ^ "Sunvepra (asunaprevir) soft gelatin capsules 100 mg. Registration certificate". State Register of Medicines (in Russian). Retrieved 26 August 2015.
  4. ^ "A Phase 3 Study in Combination With BMS-790052 and BMS-650032 in Japanese Hepatitis C Virus (HCV) Patients". ClinicalTrials.gov. 23 September 2015.
  5. ^ C. Reviriego (2012). "Asunaprevir. HCV serine protein NS3 inhibitor, Treatment of hepatitis C virus". Drugs of the Future. 37 (4): 247–254. doi:10.1358/dof.2012.037.04.1789350.
  6. ^ Lok AS, Gardiner DF, Lawitz E, Martorell C, Everson GT, Ghalib R, et al. (January 2012). "Preliminary study of two antiviral agents for hepatitis C genotype 1". The New England Journal of Medicine. 366 (3): 216–24. doi:10.1056/NEJMoa1104430. PMID 22256805.
  7. ^ "Bristol-Myers' Daclatasvir, Asunaprevir Cured 77%: Study". Bloomberg. 19 April 2012.
  8. ^ AASLD: Daclatasvir plus Asunaprevir Rapidly Suppresses HCV in Prior Null Responders Archived 2015-02-08 at the Wayback Machine. Highleyman, L. HIVandHepatitis.com. 8 November 2011.


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