NS2

[(2~{S})-2-(6-chloranyl-7-methyl-1~{H}-benzimidazol-2-yl)-2-methyl-pyrrolidin-1-yl]-[5-methoxy-2-(1,2,3-triazol-2-yl)phenyl]methanone

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

Help

Find related ligands:

Chemical Details

Formal Charge0
Atom Count55
Chiral Atom Count1
Bond Count59
Aromatic Bond Count21
2D diagram of NS2
Toggle HydrogenToggle Labels

Chemical Component Summary

Name[(2~{S})-2-(6-chloranyl-7-methyl-1~{H}-benzimidazol-2-yl)-2-methyl-pyrrolidin-1-yl]-[5-methoxy-2-(1,2,3-triazol-2-yl)phenyl]methanone
Systematic Name (OpenEye OEToolkits)[(2~{S})-2-(6-chloranyl-7-methyl-1~{H}-benzimidazol-2-yl)-2-methyl-pyrrolidin-1-yl]-[5-methoxy-2-(1,2,3-triazol-2-yl)phenyl]methanone
FormulaC23 H23 Cl N6 O2
Molecular Weight450.921
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESCACTVS3.385COc1ccc(n2nccn2)c(c1)C(=O)N3CCC[C]3(C)c4[nH]c5c(C)c(Cl)ccc5n4
SMILESOpenEye OEToolkits2.0.7Cc1c(ccc2c1[nH]c(n2)C3(CCCN3C(=O)c4cc(ccc4n5nccn5)OC)C)Cl
Canonical SMILESCACTVS3.385 COc1ccc(n2nccn2)c(c1)C(=O)N3CCC[C@@]3(C)c4[nH]c5c(C)c(Cl)ccc5n4
Canonical SMILESOpenEye OEToolkits2.0.7 Cc1c(ccc2c1[nH]c(n2)[C@@]3(CCCN3C(=O)c4cc(ccc4n5nccn5)OC)C)Cl
InChIInChI1.03 InChI=1S/C23H23ClN6O2/c1-14-17(24)6-7-18-20(14)28-22(27-18)23(2)9-4-12-29(23)21(31)16-13-15(32-3)5-8-19(16)30-25-10-11-26-30/h5-8,10-11,13H,4,9,12H2,1-3H3,(H,27,28)/t23-/m0/s1
InChIKeyInChI1.03 NBGABHGMJVIVBW-QHCPKHFHSA-N

Drug Info: DrugBank

DrugBank IDDB15031 
NameDaridorexant
Groups approved
DescriptionDaridorexant, formerly known as nemorexant, is a selective dual orexin receptor antagonist used to treat insomnia. Insomnia is characterized by difficulties with sleep onset and/or sleep maintenance and impairment of daytime functioning. It chronically affects the person's daily functioning and long-term health effects, as insomnia is often associated with comorbidities such as hypertension, diabetes, and depression. Conventional treatments for insomnia include drugs targeting gamma-aminobutyric acid type-A (GABA-A), serotonin, histamine, or melatonin receptors; however, undesirable side effects are frequently reported, such as next-morning residual sleepiness, motor incoordination, falls, memory and cognitive impairment. Novel drugs that target orexin receptors gained increasing attention after discovering the role of orexin signalling pathway in wakefulness and [almorexant], an orexin receptor antagonist that improved sleep. Daridorexant was designed via an intensive drug discovery program to improve the potency and maximize the duration of action while minimizing next-morning residual activity.[A244225] Daridorexant works on orexin receptors OX1R and OX2R to block the binding of orexins, which are wake-promoting neuropeptides and endogenous ligands to these receptors. Daridorexant reduces overactive wakefulness: in the investigational trials, daridorexant reportedly improved sleep and daytime functioning in patients with insomnia.[A244225] It was approved by the FDA on January 10, 2022, under the name QUVIVIQ.[L39660] as the second orexin receptor antagonist approved to treat insomnia following [suvorexant].[A244280] Daridorexant was approved by the European Commission on May 3, 2022, as the first dual orexin receptor antagonist approved in the market,[L41725] and by Health Canada on April 26, 2023.[L46307]
Synonyms
  • ACT-541468
  • Nemorexant
  • Daridorexant
Brand NamesQuviviq
IndicationIn the US and Europe, daridorexant is indicated for the treatment of adult patients with insomnia characterized by difficulties with sleep onset and/or sleep maintenance.[L39655, L46307] The European prescribing information states that insomnia should be characterized by symptoms that are present for at least three months and have a considerable impact on daytime functioning.[L41720]
Categories
  • Central Nervous System Depressants
  • Cytochrome P-450 CYP3A Substrates
  • Cytochrome P-450 CYP3A4 Substrates
  • Cytochrome P-450 Substrates
  • Orexin Receptor Antagonists
CAS number1505484-82-1

Drug Targets

NameTarget SequencePharmacological ActionActions
Orexin receptor type 1MEPSATPGAQMGVPPGSREPSPVPPDYEDEFLRYLWRDYLYPKQYEWVLI...unknownantagonist
Orexin receptor type 2MSGTKLEDSPPCRNWSSASELNETQEPFLNPTDYDDEEFLRYLWREYLHP...unknownantagonist
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
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 CHEMBL4297590
PubChem 91801202
ChEMBL CHEMBL4297590