berotralstat   Click here for help

GtoPdb Ligand ID: 11347

Synonyms: BCX-7353 | BCX7353 | Orladeyo®
Approved drug PDB Ligand
berotralstat is an approved drug (FDA (2020), EMA (2021))
Compound class: Synthetic organic
Comment: Berotralstat (BCX7353) is an orally bioavailable inhibitor of plasma kallikrein, a proteinase that is encoded by the KLKB1 gene in humans [4]. Plasma kallikrein cleaves Lys-Arg and Arg-Ser bonds in (human) kininogen to release bradykinin. Inhibition of this activity is exploited to reduce bradykinin levels in human disease where abnormally elevated bradykinin induces pathologic vascular permeability and swelling, as seen in patients with hereditary angioedema (HAE; caused by loss of C1 inhibitor SERPING1 expression).
The 'flat' structure of berotralstat with no specified stereochemistry is claimed as compound 52h in Biocryst Pharmaceuticals' patent WO2015134998A1 [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 108.24
Molecular weight 562.21
XLogP 4.86
No. Lipinski's rules broken 0
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Canonical SMILES NCc1cccc(c1)n1nc(cc1C(=O)Nc1cc(ccc1F)[C@@H](c1cccc(c1)C#N)NCC1CC1)C(F)(F)F
Isomeric SMILES NCc1cccc(c1)n1nc(cc1C(=O)Nc1cc(ccc1F)[C@@H](c1cccc(c1)C#N)NCC1CC1)C(F)(F)F
InChI InChI=1S/C30H26F4N6O/c31-24-10-9-22(28(37-17-18-7-8-18)21-5-1-3-19(11-21)15-35)13-25(24)38-29(41)26-14-27(30(32,33)34)39-40(26)23-6-2-4-20(12-23)16-36/h1-6,9-14,18,28,37H,7-8,16-17,36H2,(H,38,41)/t28-/m1/s1
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Molecular structure representations generated using Open Babel