NRK

(1~{R},2~{S})-2-[(2,4-dimethylpyrimidin-5-yl)oxymethyl]-~{N}-(5-fluoranylpyridin-2-yl)-2-(3-fluorophenyl)cyclopropane-1-carboxamide

Created: 2019-12-11
Last modified:  2020-01-15

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Chemical Details

Formal Charge0
Atom Count50
Chiral Atom Count2
Bond Count53
Aromatic Bond Count18
2D diagram of NRK
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Chemical Component Summary

Name(1~{R},2~{S})-2-[(2,4-dimethylpyrimidin-5-yl)oxymethyl]-~{N}-(5-fluoranylpyridin-2-yl)-2-(3-fluorophenyl)cyclopropane-1-carboxamide
Systematic Name (OpenEye OEToolkits)(1~{R},2~{S})-2-[(2,4-dimethylpyrimidin-5-yl)oxymethyl]-~{N}-(5-fluoranylpyridin-2-yl)-2-(3-fluorophenyl)cyclopropane-1-carboxamide
FormulaC22 H20 F2 N4 O2
Molecular Weight410.417
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESCACTVS3.385Cc1ncc(OC[C]2(C[CH]2C(=O)Nc3ccc(F)cn3)c4cccc(F)c4)c(C)n1
SMILESOpenEye OEToolkits2.0.7Cc1c(cnc(n1)C)OCC2(CC2C(=O)Nc3ccc(cn3)F)c4cccc(c4)F
Canonical SMILESCACTVS3.385 Cc1ncc(OC[C@]2(C[C@H]2C(=O)Nc3ccc(F)cn3)c4cccc(F)c4)c(C)n1
Canonical SMILESOpenEye OEToolkits2.0.7 Cc1c(cnc(n1)C)OC[C@]2(C[C@H]2C(=O)Nc3ccc(cn3)F)c4cccc(c4)F
InChIInChI1.03 InChI=1S/C22H20F2N4O2/c1-13-19(11-25-14(2)27-13)30-12-22(15-4-3-5-16(23)8-15)9-18(22)21(29)28-20-7-6-17(24)10-26-20/h3-8,10-11,18H,9,12H2,1-2H3,(H,26,28,29)/t18-,22+/m0/s1
InChIKeyInChI1.03 MUGXRYIUWFITCP-PGRDOPGGSA-N

Drug Info: DrugBank

DrugBank IDDB11951 
NameLemborexant
Groups
  • approved
  • investigational
DescriptionLemborexant is a novel dual orexin receptor antagonist used in the treatment of insomnia characterized by difficulties with sleep onset and/or sleep maintenance.[L10863] Recent research in the field of sleep disorders has revealed that insomnia is likely driven not by the inability of the brain to "switch on" sleep-related circuits, but rather an inability to "switch-off" wake-promoting circuits.[A189006,A189030] Whereas historically popular pharmacologic treatments for insomnia (e.g. [zopiclone], [zolpidem], benzodiazepines) focus on enhancing sleep drive via modulation of GABA and melatonin receptors, lemborexant and other orexin antagonists (e.g. [suvorexant]) act to counteract inappropriate wakefulness.[A189006] This novel mechanism of action offers potential advantages over classic hypnotic agents, including a more favorable adverse effect profile and potentially greater efficacy, and may signal the beginning of a new wave of treatment options for patients suffering from insomnia.[A189006]
SynonymsLemborexant
Brand NamesDayvigo
IndicationLemborexant is indicated for the treatment of adult patients with insomnia characterized by difficulties with sleep onset and/or sleep maintenance.[L10863]
Categories
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Cytochrome P-450 CYP2B6 Inducers
  • Cytochrome P-450 CYP2B6 Inducers (strength unknown)
  • Cytochrome P-450 CYP3A Inducers
ATC-CodeN05CM21
CAS number1369764-02-2

Drug Targets

NameTarget SequencePharmacological ActionActions
Orexin receptor type 1MEPSATPGAQMGVPPGSREPSPVPPDYEDEFLRYLWRDYLYPKQYEWVLI...unknownantagonist
Orexin receptor type 2MSGTKLEDSPPCRNWSSASELNETQEPFLNPTDYDDEEFLRYLWREYLHP...unknownantagonist
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
Cytochrome P450 3A5MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...unknownsubstrate
Cytochrome P450 2B6MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...unknowninducer
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL3545367
PubChem 56944144
ChEMBL CHEMBL3545367