Asunaprevir

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
CAS Number	630420-16-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:134723;
ChEMBL	ChEMBL2105735;
ChemSpider	17235944;
DrugBank	DB11586;
ECHA InfoCard	100.206.482
IUPHAR/BPS	10882;
KEGG	D10093 ;
PubChem CID	16076883;
UNII	S9X0KRJ00S ;
	InChI 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;
	SMILES 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
Chemical formula	C35H46ClN5O9S
Molar mass	748.29 g·mol−1
Pharmacology
ATC code	J05AP06 (WHO)
Legal status	AU: S4 (Prescription only); CA: ℞-only;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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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

^ "Prescription medicines: registration of new chemical entities in Australia, 2015". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.
^ "Health Canada New Drug Authorizations: 2016 Highlights". Health Canada. 14 March 2017. Retrieved 7 April 2024.
^ "Sunvepra (asunaprevir) soft gelatin capsules 100 mg. Registration certificate". State Register of Medicines (in Russian). Retrieved 26 August 2015.
^ "A Phase 3 Study in Combination With BMS-790052 and BMS-650032 in Japanese Hepatitis C Virus (HCV) Patients". ClinicalTrials.gov. 23 September 2015.
^ 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.
^ 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.
^ "Bristol-Myers' Daclatasvir, Asunaprevir Cured 77%: Study". Bloomberg. 19 April 2012.
^ 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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[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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