linrodostat   

GtoPdb Ligand ID: 9707

Synonyms: BMS-986205 | BMS986205 | Compound 2 [PMID: 29531094] | Example 19 [US20160137652A1]
Compound class: Synthetic organic
Comment: Linrodostat (BMS-986205) is a potent and selective, orally available indoleamine 2,3-dioxygenase 1 (IDO1) inhibitor [3], being investigated as an immuno-therapeutic for various malignancies. The INN for linrodostat specifies the (R) stereoisomer. The chemical structure is claimed as example 19 in Flexus Bioscience's patent US2016137652 [1] and the compound is being taken through clinical development by Bristol-Myers Squibb. Mechanistically, linrodostat competes with the heme cofactor for binding to the apo-form of the enzyme, and once bound prevents heme from rebinding [3].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 41.99
Molecular weight 410.16
XLogP 6.53
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES Clc1ccc(cc1)NC(=O)C(C1CCC(CC1)c1ccnc2c1cc(F)cc2)C
Isomeric SMILES Clc1ccc(cc1)NC(=O)[C@@H](C1CCC(CC1)c1ccnc2c1cc(F)cc2)C
InChI InChI=1S/C24H24ClFN2O/c1-15(24(29)28-20-9-6-18(25)7-10-20)16-2-4-17(5-3-16)21-12-13-27-23-11-8-19(26)14-22(21)23/h6-17H,2-5H2,1H3,(H,28,29)/t15-,16?,17?/m1/s1
InChI Key KRTIYQIPSAGSBP-KLAILNCOSA-N
Classification
Compound class Synthetic organic
IUPAC Name
(2R)-N-(4-chlorophenyl)-2-[4-(6-fluoroquinolin-4-yl)cyclohexyl]propanamide
International Nonproprietary Names
INN number INN
10894 linrodostat
Synonyms
BMS-986205 | BMS986205 | Compound 2 [PMID: 29531094] | Example 19 [US20160137652A1]
Database Links
GtoPdb PubChem SID 348353666
PubChem CID 121328278
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