(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid

ID: ALA2048028

Cas Number: 1025967-78-5

PubChem CID: 11965427

Product Number: L420387, Order Now?

Max Phase: Approved

First Approval: 2016

Molecular Formula: C29H24Cl2N2O7S

Molecular Weight: 615.49

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Lifitegrast | SAR 1118 | SAR-1118 | SHP-606 | SHP606 | Lifitegrast|1025967-78-5|Xiidra|SAR 1118|SAR-1118|SHP606|SHP-606|(S)-2-(2-(benzofuran-6-carbonyl)-5,7-dichloro-1,2,3,4-tetrahydroisoquinoline-6-carboxamido)-3-(3-(methylsulfonyl)phenyl)propanoic acid|UNII-038E5L962W|038E5L962W|L-Phenylalanine, N-[[2-(6-benzofuranylcarbonyl)-5,7-dichloro-1,2,3,4-tetrahydro-6-isoquinolinyl]carbonyl]-3-(methylsulfonyl)-|CHEMBL2048028|CHEBI:133023|DTXSID60145345|SAR1118|L-Phenylalanine, N-((2-(6-benzofuranylcarbShow More⌵

Synonyms from Alternative Forms(3): SAR 1118-023 | SAR-1118-023 | Lifitegrast sodium

Trade Names(1): Xiidra

Canonical SMILES:  CS(=O)(=O)c1cccc(C[C@H](NC(=O)c2c(Cl)cc3c(c2Cl)CCN(C(=O)c2ccc4ccoc4c2)C3)C(=O)O)c1

Standard InChI:  InChI=1S/C29H24Cl2N2O7S/c1-41(38,39)20-4-2-3-16(11-20)12-23(29(36)37)32-27(34)25-22(30)13-19-15-33(9-7-21(19)26(25)31)28(35)18-6-5-17-8-10-40-24(17)14-18/h2-6,8,10-11,13-14,23H,7,9,12,15H2,1H3,(H,32,34)(H,36,37)/t23-/m0/s1

Standard InChI Key:  JFOZKMSJYSPYLN-QHCPKHFHSA-N

Molfile:  

     RDKit          2D

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    0.2734   -4.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2115   -3.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7725   -4.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4870   -4.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2014   -2.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9159   -3.2714    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3449   -3.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6304   -2.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3449   -4.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0593   -5.3339    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.0593   -4.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4883   -4.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4883   -5.3339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2027   -4.0964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7738   -3.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4883   -2.8589    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.0593   -2.8589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9172   -4.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.0606   -4.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4896   -4.0964    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.7751   -4.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7751   -5.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0606   -5.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.9021   -4.8109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6317   -5.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9172   -5.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2014   -2.0339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2027   -5.7464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  2  0
  2  9  2  0
  3  1  1  0
  3  6  1  0
  4  5  1  0
  4  7  1  0
  6  5  2  0
  7  8  2  0
  9 10  1  0
  9  8  1  0
 10 11  1  0
 11 15  1  0
 12 13  1  0
 12 25  1  0
 13 11  1  0
 14 12  2  0
 14 18  1  0
 15 16  1  0
 16 14  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 22 20  1  0
 23 24  1  0
 23 19  1  0
 25 23  2  0
 26 22  1  0
 26 33  1  1
 26 39  1  0
 27 28  2  0
 27 34  1  0
 28 30  1  0
 29 30  1  0
 29 37  1  0
 30 31  2  0
 32 31  1  0
 33 27  1  0
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 35 29  2  0
 36 29  2  0
 39 38  2  0
 10 40  2  0
 39 41  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2048028

   Lifitegrast

2. Alternative Forms:

   

   ALA2048028

   Lifitegrast sodium
3. 

   ALA2048028

   CID 70684132

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: Yes

First In Class: Yes

Black Box: No

Chirality: Yes

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 615.49

Molecular Weight (Monoisotopic): 614.0681

AlogP: 4.77

#Rotatable Bonds: 7

Polar Surface Area: 133.99

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.27

CX Basic pKa: ┄

CX LogP: 4.02

CX LogD: 0.59

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.31

Np Likeness Score: -0.74

References

1. Zhong M, Gadek TR, Bui M, Shen W, Burnier J, Barr KJ, Hanan EJ, Oslob JD, Yu CH, Zhu J, Arkin MR, Evanchik MJ, Flanagan WM, Hoch U, Hyde J, Prabhu S, Silverman JA, Wright J..  (2012)  Discovery and Development of Potent LFA-1/ICAM-1 Antagonist SAR 1118 as an Ophthalmic Solution for Treating Dry Eye.,  3  (3): [PMID:24900456] [10.1021/ml2002482]

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

3. Unpublished dataset, 

4. WHO Anatomical Therapeutic Chemical Classification, 

5. Unpublished dataset, 

Source

Source(5):

• Scientific Literature
• Clinical Candidates
• FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book)
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification