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Merck
CN

SML3660

RPL554

≥98% (HPLC)

Synonym(s):

9,10-Dimethoxy-2(2,4,6-trimethylphenylimino)-3-(N-carbamoyl-2-aminoethyl)-3,4,6,7-tetrahydro-2H-pyrimido[6,1-a]isoquinolin-4-one], Ensifentrine, N-[2-[6,7-Dihydro-9,10-dimethoxy-4-oxo-2-[(2,4,6-trimethylphenyl)imino]-2H-pyrimido[6,1-a]isoquinolin-3(4H)-yl]ethyl]-urea, RPL 554, [2-[6,7-Dihydro-9,10-dimethoxy-4-oxo-2-[(2,4,6-trimethylphenyl)imino]-2H-pyrimido[6,1-a]isoquinolin-3(4H)-yl]ethyl]-urea

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About This Item

Empirical Formula (Hill Notation):
C26H31N5O4
CAS Number:
298680-25-8
Molecular Weight:
477.56
UNSPSC Code:
12352200
NACRES:
NA.21
MDL number:
MFCD09970918

Key Documents

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assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear (Warmed)

storage temp.

-10 to -25°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Long acting, potent and specific dual inhibitor of PDE 3/4; activates CFTR mutant channels
RPL554 (Ensifentrine) is a long acting, potent and specific dual inhibitor of PDE 3/4 (phosphodiesterase 3 and 4). RPL554 displays a broad range of both bronchoprotective and anti-inflammatory activities. Also, RPL554 synergizes with anti-muscarinic drugs in inhibition of ASM tone. RPL554 (Ensifentrine) exhibits anti-inflammatory effects through reduced production of the monocyte chemoattractant protein-1 (MCP-1) and granulocyte monocyte colony stimulating factor (GM-CSF) in cystic fibrosis bronchial epithelial cells during challenge with Interleukin-1β.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000255013
0000255015
0000246066
0000246066
0000255015

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Mark J Turner et al.
The Journal of pharmacology and experimental therapeutics, 375(3), 414-429 (2020-10-06)
Cystic fibrosis (CF) is caused by mutations in the cystic fibrosis transmembrane conductance regulator (CFTR) anion channel that impair airway salt and fluid secretion. Excessive release of proinflammatory cytokines and chemokines by CF bronchial epithelium during airway infection leads to
Victoria Boswell-Smith et al.
The Journal of pharmacology and experimental therapeutics, 318(2), 840-848 (2006-05-10)
The pharmacology of two novel, trequinsin-like PDE3/4 inhibitors, RPL554 [9,10-dimethoxy-2(2,4,6-trimethylphenylimino)-3-(N-carbamoyl-2-aminoethyl)-3,4,6,7-tetrahydro-2H-pyrimido-[6,1-a]isoquinolin-4-one] and RPL565 [6,7-dihydro-2-(2,6-diisopropylphenoxy)-9,10-dimethoxy-4H-pyrimido[6,1-a]isoquinolin-4-one], has been investigated in a number of in vitro and in vivo assays. Electrical field stimulation-induced contraction of guinea pig superfused isolated tracheal preparations was significantly inhibited
Luigino Calzetta et al.
The Journal of pharmacology and experimental therapeutics, 346(3), 414-423 (2013-06-15)
The phosphodiesterase (PDE) enzyme family hydrolyzes cAMP and cGMP, second messengers that regulate a variety of cellular processes, including airway smooth muscle (ASM) relaxation and the inhibition of inflammatory cells. We investigated the activity of RPL554 [9,10-dimethoxy-2(2,4,6-trimethylphenylimino)-3-(n-carbamoyl-2-aminoethyl)-3,4,6,7-tetrahydro-2H-pyrimido[6,1-a]isoquinolin-4-one], a dual PDE3/PDE4

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