Revefenacin

Chemical compound From Wikipedia, the free encyclopedia

Revefenacin, sold under the brand name Yupelri, is a medication for the treatment of chronic obstructive pulmonary disease (COPD). It was approved for use in the United States in 2018.[1] It was developed by Theravance Biopharma and is marketed by Mylan. Revefenacin is formulated as a solution that is nebulized and inhaled.[2]

Trade namesYupelri
AHFS/Drugs.comMonograph
MedlinePlusa619009
License data
Quick facts Clinical data, Trade names ...
Revefenacin
Clinical data
Trade namesYupelri
AHFS/Drugs.comMonograph
MedlinePlusa619009
License data
Routes of
administration		Inhalation
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC35H43N5O4
Molar mass597.760 g·mol−1
3D model (JSmol)
  • CN(CCN1CCC(CC1)OC(=O)NC2=CC=CC=C2C3=CC=CC=C3)C(=O)C4=CC=C(C=C4)CN5CCC(CC5)C(=O)N
  • InChI=1S/C35H43N5O4/c1-38(34(42)29-13-11-26(12-14-29)25-40-19-15-28(16-20-40)33(36)41)23-24-39-21-17-30(18-22-39)44-35(43)37-32-10-6-5-9-31(32)27-7-3-2-4-8-27/h2-14,28,30H,15-25H2,1H3,(H2,36,41)(H,37,43)
  • Key:FYDWDCIFZSGNBU-UHFFFAOYSA-N
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Revefenacin is a bronchodilator that exerts its effect as a long-acting muscarinic antagonist.[3]

Society and culture

Brand names

In some countries, Yupelri is marketed by Viatris after Upjohn merged with Mylan to create Viatris.[4][5]

Synthesis

The synthesis of revefenacin was recently reported.[6]

skin-invert-image
skin-invert-image

The reaction between 1-benzylpiperidin-4-ol [4727-72-4] (1) and 1-isocyanato-2-phenylbenzene [605-677-1] (2) gave the urethane [171723-80-1]. Next acid transfer hydrogenation cleaved the benzyl protecting group to give [171722-92-2] (3). The reductive amination with Cbz-sarcosinal [107201-33-2] (4). Catalytic hydrogenation then removed the Cbz group to give [743460-48-2] (5). Amide formation with 4-formylbenzoic acid [619-66-9] (6) gave [864760-28-1] (7). Lastly, a reductive amination reaction with isonipecotamide [39546-32-2] (8) completed the synthesis of revefenacin (9).

References

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