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Pibrentasvir

Pibrentasvir

Synopsis, Chemistry

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Also known as: 1353900-92-1, Abt-530, Pibrentasvir [usan], Abt 530, A-1325912.0, Abt530

Molecular Formula

C₅₇H₆₅F₅N₁₀O₈

Molecular Weight

1113.2 g/mol

InChI Key

VJYSBPDEJWLKKJ-NLIMODCCSA-N

FDA UNII

2WU922TK3L

Pibrentasvir is a direct acting antiviral agent and Hepatitis C virus (HCV) NS5A inhibitor that targets the the viral RNA replication and viron assembly. In combination with [DB13879], pibrentastiv is a useful therapy for patients who experienced therapeutic failure from other NS5A inhibitors. In cell cultures, the emergence of amino acid substitutions at known NS5A inhibitor resistance-associated positions in HCV genotype 1a, 2a or 3a replicons led to reduced susceptibility and resistance to pibrentasvir. These resistance-associated amino acid substitutions included Q30D/deletion, Y93D/H/N or H58D +Y93H in genotype 1a replicons, F28S + M31I or P29S + K30G in genotype 2a replicons, and Y93H in genotype 3a replicons. Individual NS5A amino acid substitutions that reduced susceptibility to pibrentasvir include M28G or Q30D in a genotype 1a replicon and P32-deletion in a genotype 1b replicon. Pibrentasvir is available as an oral combination therapy with [DB13879] under the brand name Mavyret. This fixed-dose combination therapy was FDA-approved in August 2017 to treat adults with chronic hepatitis C virus (HCV) genotypes 1-6 without cirrhosis (liver disease) or with mild cirrhosis, including patients with moderate to severe kidney disease and those who are on dialysis. Mavyret is also indicated for HCV genotype 1-infected patients who have been previously treated with regimens either containing an NS5A inhibitor or an NS3/4A protease inhibitor, but not both. Hepatitis C viral infection often leads to decreased liver function and subsequent liver failure, causing a significantly negative impact on the patients' quality of life. The ultimate goal of the combination treatment is to achieve sustained virologic response (SVR) and cure the patients from the infection. In clinical trials, this combination therapy achieved SVR12 rate, or undetectable Hepatitis C for twelve or more weeks after the end of treatment, of 93% across genotypes 1a, 2a, 3a, 4, 5 and 6.

Pibrentasvir is a Hepatitis C Virus NS5A Inhibitor. The mechanism of action of pibrentasvir is as a P-Glycoprotein Inhibitor, and Breast Cancer Resistance Protein Inhibitor, and Organic Anion Transporting Polypeptide 1B1 Inhibitor, and Organic Anion Transporting Polypeptide 1B3 Inhibitor, and Cytochrome P450 3A Inhibitor, and Cytochrome P450 1A2 Inhibitor, and UGT1A1 Inhibitor.

1 2D Structure

Pibrentasvir

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl N-[(2S,3R)-1-[(2S)-2-[6-[(2R,5R)-1-[3,5-difluoro-4-[4-(4-fluorophenyl)piperidin-1-yl]phenyl]-5-[6-fluoro-2-[(2S)-1-[(2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoyl]pyrrolidin-2-yl]-3H-benzimidazol-5-yl]pyrrolidin-2-yl]-5-fluoro-1H-benzimidazol-2-yl]pyrrolidin-1-yl]-3-methoxy-1-oxobutan-2-yl]carbamate

2.1.2 InChI

InChI=1S/C57H65F5N10O8/c1-29(77-3)49(67-56(75)79-5)54(73)70-19-7-9-47(70)52-63-41-25-35(37(59)27-43(41)65-52)45-15-16-46(72(45)34-23-39(61)51(40(62)24-34)69-21-17-32(18-22-69)31-11-13-33(58)14-12-31)36-26-42-44(28-38(36)60)66-53(64-42)48-10-8-20-71(48)55(74)50(30(2)78-4)68-57(76)80-6/h11-14,23-30,32,45-50H,7-10,15-22H2,1-6H3,(H,63,65)(H,64,66)(H,67,75)(H,68,76)/t29-,30-,45-,46-,47+,48+,49+,50+/m1/s1

2.1.3 InChI Key

VJYSBPDEJWLKKJ-NLIMODCCSA-N

2.1.4 Canonical SMILES

CC(C(C(=O)N1CCCC1C2=NC3=C(N2)C=C(C(=C3)F)C4CCC(N4C5=CC(=C(C(=C5)F)N6CCC(CC6)C7=CC=C(C=C7)F)F)C8=CC9=C(C=C8F)N=C(N9)C1CCCN1C(=O)C(C(C)OC)NC(=O)OC)NC(=O)OC)OC

2.1.5 Isomeric SMILES

C[C@H]([C@@H](C(=O)N1CCC[C@H]1C2=NC3=C(N2)C=C(C(=C3)F)[C@H]4CC[C@@H](N4C5=CC(=C(C(=C5)F)N6CCC(CC6)C7=CC=C(C=C7)F)F)C8=CC9=C(C=C8F)N=C(N9)[C@@H]1CCCN1C(=O)[C@H]([C@@H](C)OC)NC(=O)OC)NC(=O)OC)OC

2.2 Other Identifiers

2.2.1 UNII

2WU922TK3L

2.3 Synonyms

2.3.1 MeSH Synonyms

1. A-1325912.0

2. Abt-530

3. Dimethyl N,n'-(((2r,5r)-1-(3,5-difluoro-4-(4-(4-fluorophenyl)piperidin-1-yl)phenyl)pyrrolidine-2,5-diyl)bis((6-fluoro-1h-benzimidazole-5,2-diyl)((2s)-pyrrolidine-2,1-diyl)((2s,3r)-3-methoxy-1-oxobutane-1,2-diyl)))biscarbamate

2.3.2 Depositor-Supplied Synonyms

1. 1353900-92-1

2. Abt-530

3. Pibrentasvir [usan]

4. Abt 530

5. A-1325912.0

6. Abt530

7. 2wu922tk3l

8. 1353900-92-1 (free)

9. Dimethyl N,n'-(((2r,5r)-1-(3,5-difluoro-4-(4-(4-fluorophenyl)piperidin-1-yl)phenyl)pyrrolidine-2,5-diyl)bis((6-fluoro-1h-benzimidazole-5,2-diyl)((2s)-pyrrolidine-2,1-diyl)((2s,3r)-3-methoxy-1-oxobutane-1,2-diyl)))biscarbamate

10. Dimethyl ((2s,2's,3r,3'r)-((2s,2's)-(((2r,5r)-1-(3,5-difluoro-4-(4-(4-fluorophenyl)piperidin-1-yl)phenyl)pyrrolidine-2,5-diyl)bis(6-fluoro-1h-benzo[d]imidazole-5,2-diyl))bis(pyrrolidine-2,1-diyl))bis(3-methoxy-1-oxobutane-1,2-diyl))dicarbamate

11. Methyl N-[(2s,3r)-1-[(2s)-2-[6-[(2r,5r)-1-[3,5-difluoro-4-[4-(4-fluorophenyl)piperidin-1-yl]phenyl]-5-[6-fluoro-2-[(2s)-1-[(2s,3r)-3-methoxy-2-(methoxycarbonylamino)butanoyl]pyrrolidin-2-yl]-3h-benzimidazol-5-yl]pyrrolidin-2-yl]-5-fluoro-1h-benzimidazol-2-yl]pyrrolidin-1-yl]-3-methoxy-1-oxobutan-2-yl]carbamate

12. Unii-2wu922tk3l

13. Abt-530;pibrentasvir

14. Pibrentasvir [mi]

15. Pibrentasvir(abt-530)

16. Pibrentasvir [inn]

17. Pibrentasvir [jan]

18. Pibrentasvir (abt-530)

19. Pibrentasvir [who-dd]

20. Pibrentasvir (jan/usan/inn)

21. Schembl2756579

22. Chembl3545123

23. Schembl17639956

24. Gtpl11268

25. Ex-a865

26. Dtxsid601027946

27. Pibrentasvir [orange Book]

28. C57h65f5n10o8

29. Bdbm50453100

30. Mavyret Component Pibrentasvir

31. S9641

32. Cs-8135

33. Db13878

34. Ac-33418

35. Bs-15250

36. J3.646.121g

37. D10816

38. J-690144

39. Q47495788

40. A 1325912.0

41. Carbamic Acid, N,n'-(((2r,5r)-1-(3,5-difluoro-4-(4-(4-fluorophenyl)-1-piperidinyl)phenyl)-2,5-pyrrolidinediyl)bis((6-fluoro-1h-benzimidazole-5,2-diyl)-(2s)-2,1-pyrrolidinediyl((1s)-1-((1r)-1-methoxyethyl)-2-oxo-2,1-ethanediyl)))bis-, C,c'-dimethyl Ester

42. Methyl ((2s,3r)-1-((2s)-2-(5-((2r,5r)-1-(3,5-difluoro-4-(4-(4-fluorophenyl)piperidin-1-yl)phenyl)-5-(6-fluoro-2-((2s)-1-(n-(methoxycarbonyl)-o-methyl-l-threonyl)pyrrolidin-2-yl)-1h-benzimidazol-5-yl)pyrrolidin-2-yl)-6-fluoro-1h-benzimidazol-2-yl)pyrrolidin-1-yl)-3-methoxy-1-oxobutan-2-yl)carbamate

2.4 Create Date

2012-08-19

3 Chemical and Physical Properties

Molecular Formula	C₅₇H₆₅F₅N₁₀O₈
Molecular Weight	1113.2 g/mol
XLogP3	7.4
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	17
Rotatable Bond Count	17
Exact Mass	1112.49069988 g/mol
Monoisotopic Mass	1112.49069988 g/mol
Topological Polar Surface Area	200 Å²
Heavy Atom Count	80
Formal Charge	0
Complexity	2000
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Indicated for the treatment of adult patients with chronic hepatitis C virus (HCV) genotype 1, 2, 3, 4, 5 or 6 infection without cirrhosis or with compensated cirrhosis (Child-Pugh A). MAVYRET is also indicated for the treatment of adult patients with HCV genotype 1 infection, who previously have been treated with a regimen containing an HCV NS5A inhibitor or an NS3/4A protease inhibitor (PI), but not both.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Pibrentasvir is a pan-genotypic . According to HCV replicon assays, pibrentasvir has EC50 values ranging from 0.08-4.6 nM agaisnt laboratory and clinical isolates from subtypes 1a, 1b, 2a, 2b, 3a, 4a, 4d, 5a, and 6a, or EC50 values of 0.5-4.3 pM against laboratory and clinical isolates from subtypes 1a, 1b, 2a, 2b, 3a, 4a, 4b, 4d, 5a, 6a, 6e and 6p. It is active against common resistance-conferring substitutions in HCV genotypes 1 to 6 that confers resistance and decreased therapeutic response from other NS5A inhibitors, inluding positions 24, 28, 30, 31, 58, 92, or 93 in NS5A. In a QT study, pibrentasvir is not shown to prolong the QTc interval.

5.2 FDA Pharmacological Classification

5.2.1 Active Moiety

PIBRENTASVIR

5.2.2 FDA UNII

2WU922TK3L

5.2.3 Pharmacological Classes

Mechanisms of Action [MoA] - UGT1A1 Inhibitors

5.3 Absorption, Distribution and Excretion

Absorption

In healthy subjects, the time it takes to reach the peak plasma concentration (Tmax) is approximately 5 hours. The mean peak plasma concentration (Cmax) is 110ng/mL in non-cirrhotic HCV-infected subjects. Relative to fasting conditions, the consumption of meals increases the absorption of pibrentasvir by 40-53%.

Route of Elimination

The predominant route of elimination of the drug is biliary-fecal, where 96.6% of administered drug is excreted in feces and 0% of the drug is excreted in the urine.

5.4 Metabolism/Metabolites

Pibrentasvir is not metabolized.

5.5 Biological Half-Life

The elimination half life (t1/2) is approximately 13 hours.

5.6 Mechanism of Action

NS5A is a phosphoprotein that plays an essential role in replication, assembly and maturation of infectious viral proteins. The basal phosphorylated form of NS5A, which is maintained by C-terminal serine cluster, is key in ensuring its interaction with the viral capsid protein, or the core protein. By blocking this interaction, pibrentasvir inhibits the assembly of proteins and production of mature HCV particles. NS5A also interacts with viral and cellular proteins to form the HCV replicase complex, and supports the RNA replication of HCV.

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