Piclamilast

Piclamilast
Clinical data
ATC code	None;
Identifiers
	IUPAC name 3-(Cyclopentyloxy)-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide;
CAS Number	144035-83-6;
PubChem CID	154575;
DrugBank	EXPT02600;
ChemSpider	136184;
UNII	WM58D7C3ZT;
KEGG	D05474;
ChEBI	CHEBI:47619 ;
ChEMBL	ChEMBL42126;
CompTox Dashboard (EPA)	DTXSID3040227 ;
ECHA InfoCard	100.229.714
Chemical and physical data
Formula	C18H18Cl2N2O3
Molar mass	381.25 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=C(C=C(C=C1)C(=O)NC2=C(C=NC=C2Cl)Cl)OC3CCCC3;
	InChI InChI=1S/C18H18Cl2N2O3/c1-24-15-7-6-11(8-16(15)25-12-4-2-3-5-12)18(23)22-17-13(19)9-21-10-14(17)20/h6-10,12H,2-5H2,1H3,(H,21,22,23); Key:RRRUXBQSQLKHEL-UHFFFAOYSA-N;

Piclamilast (RP 73401), is a selective PDE4 inhibitor.^[1] It is comparable to other PDE4 inhibitors for its anti-inflammatory effects. It has been investigated for its applications to the treatment of conditions such as chronic obstructive pulmonary disease, bronchopulmonary dysplasia and asthma. It is a second generation compound that exhibits structural functionalities of the PDE4 inhibitors cilomilast and roflumilast. The structure for piclamilast was first elucidated in a 1995 European patent application.^[2] The earliest mention of the name "piclamilast" was used in a 1997 publication.^[3]

^ Beeh KM, Beier J, Lerch C, Schulz AK, Buhl R (2004). "Effects of piclamilast, a selective phosphodiesterase-4 inhibitor, on oxidative burst of sputum cells from mild asthmatics and stable COPD patients". Lung. 182 (6): 369–77. doi:10.1007/s00408-004-2518-z. PMID 15765929. S2CID 2558906.
^ EP expired 0497564, Ashton, Michael John; Cook, David Charles & Fenton, Garry et al., "Benzamides", published 1992-08-05, assigned to Rhone-Poulenc Rorer Ltd.
^ Souness JE, Houghton C, Sardar N, Withnall MT (June 1997). "Evidence that cyclic AMP phosphodiesterase inhibitors suppress interleukin-2 release from murine splenocytes by interacting with a 'low-affinity' phosphodiesterase 4 conformer". British Journal of Pharmacology. 121 (4): 743–50. doi:10.1038/sj.bjp.0701200. PMC 1564751. PMID 9208143.

[1] Beeh KM, Beier J, Lerch C, Schulz AK, Buhl R (2004). "Effects of piclamilast, a selective phosphodiesterase-4 inhibitor, on oxidative burst of sputum cells from mild asthmatics and stable COPD patients". Lung. 182 (6): 369–77. doi:10.1007/s00408-004-2518-z. PMID 15765929. S2CID 2558906.

[2] EP expired 0497564, Ashton, Michael John; Cook, David Charles & Fenton, Garry et al., "Benzamides", published 1992-08-05, assigned to Rhone-Poulenc Rorer Ltd.

[3] Souness JE, Houghton C, Sardar N, Withnall MT (June 1997). "Evidence that cyclic AMP phosphodiesterase inhibitors suppress interleukin-2 release from murine splenocytes by interacting with a 'low-affinity' phosphodiesterase 4 conformer". British Journal of Pharmacology. 121 (4): 743–50. doi:10.1038/sj.bjp.0701200. PMC 1564751. PMID 9208143.

[1]

[2]

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Clinical data

ATC code	None
Identifiers
IUPAC name 3-(Cyclopentyloxy)-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide
CAS Number	144035-83-6
PubChem CID	154575
DrugBank	EXPT02600
ChemSpider	136184
UNII	WM58D7C3ZT
KEGG	D05474
ChEBI	CHEBI:47619^Y
ChEMBL	ChEMBL42126
CompTox Dashboard (EPA)	DTXSID3040227
ECHA InfoCard	100.229.714
Chemical and physical data
Formula	C₁₈H₁₈Cl₂N₂O₃
Molar mass	381.25 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COC1=C(C=C(C=C1)C(=O)NC2=C(C=NC=C2Cl)Cl)OC3CCCC3
InChI InChI=1S/C18H18Cl2N2O3/c1-24-15-7-6-11(8-16(15)25-12-4-2-3-5-12)18(23)22-17-13(19)9-21-10-14(17)20/h6-10,12H,2-5H2,1H3,(H,21,22,23) Key:RRRUXBQSQLKHEL-UHFFFAOYSA-N