(1R,2S)-1-((2S,4R)-4-(8-bromo-2-(2-isobutyramidothiazol-4-yl)-7-methoxyquinolin-4-yloxy)-1-((S)-2-(cyclopentyloxycarbonylamino)-3,3-dimethylbutanoyl)pyrrolidine-2-carboxamido)-2-vinylcyclopropanecarboxylic acid

ID: ALA1241348

Chembl Id: CHEMBL1241348

Cas Number: 801283-95-4

PubChem CID: 42601552

Max Phase: Phase

Molecular Formula: C40H49BrN6O9S

Molecular Weight: 869.84

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BI 201335 | Faldaprevir | BI 201335 | BI-201335 | BI201335 | Faldaprevir|801283-95-4|BI201335|BI-201335|CHEMBL1241348|958X4J301A|(1R,2S)-1-((2S,4R)-4-((8-bromo-2-(2-isobutyramidothiazol-4-yl)-7-methoxyquinolin-4-yl)oxy)-1-((S)-2-(((cyclopentyloxy)carbonyl)amino)-3,3-dimethylbutanoyl)pyrrolidine-2-carboxamido)-2-vinylcyclopropane-1-carboxylic acid|N-[(Cyclopentyloxy)carbonyl]-3-Methyl-L-Valyl-(4r)-4-[(8-Bromo-7-Methoxy-2-{2-[(2-Methylpropanoyl)amino]-1,3-Thiazol-4-Yl}quinolin-4-Yl)oxy]-N-[(1r,2s)Show More⌵

Synonyms from Alternative Forms(6): Faldaprevir, sodium salt | BI 201335 NA | BI-201335 NA | BI-201335-NA | BI-201335NA | Faldaprevir sodium

Canonical SMILES:  C=C[C@@H]1C[C@]1(NC(=O)[C@@H]1C[C@@H](Oc2cc(-c3csc(NC(=O)C(C)C)n3)nc3c(Br)c(OC)ccc23)CN1C(=O)[C@@H](NC(=O)OC1CCCC1)C(C)(C)C)C(=O)O

Standard InChI:  InChI=1S/C40H49BrN6O9S/c1-8-21-17-40(21,36(51)52)46-34(49)27-15-23(18-47(27)35(50)32(39(4,5)6)44-38(53)56-22-11-9-10-12-22)55-29-16-25(26-19-57-37(43-26)45-33(48)20(2)3)42-31-24(29)13-14-28(54-7)30(31)41/h8,13-14,16,19-23,27,32H,1,9-12,15,17-18H2,2-7H3,(H,44,53)(H,46,49)(H,51,52)(H,43,45,48)/t21-,23-,27+,32-,40-/m1/s1

Standard InChI Key:  LLGDPTDZOVKFDU-XUHJSTDZSA-N

Alternative Forms

1. Parent:

   

   ALA1241348

   FALDAPREVIR

2. Alternative Forms:

   

   ALA1241348

   FALDAPREVIR SODIUM

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 869.84

Molecular Weight (Monoisotopic): 868.2465

AlogP: 6.30

#Rotatable Bonds: 13

Polar Surface Area: 198.38

Molecular Species: ACID

HBA: 11

HBD: 4

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.38

CX Basic pKa: 1.11

CX LogP: 6.51

CX LogD: 2.99

Aromatic Rings: 3

Heavy Atoms: 57

QED Weighted: 0.14

Np Likeness Score: -0.10

References

1. Llinàs-Brunet M, Bailey MD, Goudreau N, Bhardwaj PK, Bordeleau J, Bös M, Bousquet Y, Cordingley MG, Duan J, Forgione P, Garneau M, Ghiro E, Gorys V, Goulet S, Halmos T, Kawai SH, Naud J, Poupart MA, White PW..  (2010)  Discovery of a potent and selective noncovalent linear inhibitor of the hepatitis C virus NS3 protease (BI 201335).,  53  (17): [PMID:20715823] [10.1021/jm100690x]

2. White PW, Llinàs-Brunet M, Amad M, Bethell RC, Bolger G, Cordingley MG, Duan J, Garneau M, Lagacé L, Thibeault D, Kukolj G..  (2010)  Preclinical characterization of BI 201335, a C-terminal carboxylic acid inhibitor of the hepatitis C virus NS3-NS4A protease.,  54  (11): [PMID:20823284] [10.1128/aac.00787-10]

3. Moreau B, O'Meara JA, Bordeleau J, Garneau M, Godbout C, Gorys V, Leblanc M, Villemure E, White PW, Llinàs-Brunet M..  (2014)  Discovery of hepatitis C virus NS3-4A protease inhibitors with improved barrier to resistance and favorable liver distribution.,  57  (5): [PMID:23506530] [10.1021/jm400121t]

4. Lampa AK, Bergman SM, Gustafsson SS, Alogheli H, Akerblom EB, Lindeberg GG, Svensson RM, Artursson P, Danielson UH, Karlén A, Sandström A..  (2014)  Novel Peptidomimetic Hepatitis C Virus NS3/4A Protease Inhibitors Spanning the P2-P1' Region.,  5  (3): [PMID:24900813] [10.1021/ml400217r]

5. Lampa A, Alogheli H, Ehrenberg AE, Åkerblom E, Svensson R, Artursson P, Danielson UH, Karlén A, Sandström A..  (2014)  Vinylated linear P2 pyrimidinyloxyphenylglycine based inhibitors of the HCV NS3/4A protease and corresponding macrocycles.,  22  (23): [PMID:25456385] [10.1016/j.bmc.2014.10.010]

6. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

7. WHO Anatomical Therapeutic Chemical Classification, 

8. Unpublished dataset, 

9. Taylor JG, Zipfel S, Ramey K, Vivian R, Schrier A, Karki KK, Katana A, Kato D, Kobayashi T, Martinez R, Sangi M, Siegel D, Tran CV, Yang ZY, Zablocki J, Yang CY, Wang Y, Wang K, Chan K, Barauskas O, Cheng G, Jin D, Schultz BE, Appleby T, Villaseñor AG, Link JO..  (2019)  Discovery of the pan-genotypic hepatitis C virus NS3/4A protease inhibitor voxilaprevir (GS-9857): A component of Vosevi^®.,  29  (16): [PMID:31133531] [10.1016/j.bmcl.2019.03.037]

10. Ganta NM, Gedda G, Rathnakar B, Satyanarayana M, Yamajala B, Ahsan MJ, Jadav SS, Balaraju T..  (2019)  A review on HCV inhibitors: Significance of non-structural polyproteins.,  164  [PMID:30639895] [10.1016/j.ejmech.2018.12.045]

Source

Source(4):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification