CAS Number144035-83-6
Synonyms3-(cyclopentyloxy)-N-(3,5-dichloro-4-pyridyl)-4-methoxybenzamide; 3-cyclopentyloxy-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide; Piclamilast; 3-(Cyclopentyloxy)-N-(3,5-dichloro-4-pyridinyl)-4-methoxybenzamide; Cpodpmb; 3-(Cyclopentyloxy)-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide
Molecular FormulaC18H18Cl2N2O3
Molecular Weight381.25
Purity≥98 (HPLC)%
Density1.4±0.1 g/cm3
Boiling Point447.8±45.0 °C at 760 mmHg
Appearancepowder
Symbol
Signal WordWarning
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 144035-83-6 |
| Catalog No. | 2A-9067452 |
| Chinese Name | Piclamilast |
| Synonyms | 3-(cyclopentyloxy)-N-(3,5-dichloro-4-pyridyl)-4-methoxybenzamide; 3-cyclopentyloxy-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide; Piclamilast; 3-(Cyclopentyloxy)-N-(3,5-dichloro-4-pyridinyl)-4-methoxybenzamide; Cpodpmb; 3-(Cyclopentyloxy)-N-(3,5-dichloropyridin-4-yl)-4-methoxybenzamide |
| Molecular Formula | C18H18Cl2N2O3 |
| Molecular Weight | 381.25 |
| Purity | ≥98 (HPLC) |
| Density | 1.4±0.1 g/cm3 |
| Boiling Point | 447.8±45.0 °C at 760 mmHg |
| Appearance | powder |
| Storage Condition | 2-8°C, sealed, dry |
| Application | Piclamilast (RP 73401) is a potent inhibitor of phosphodiesterase 4 (PDE4) with IC50 values of 16 nM and 2 nM in porcine aorta and soluble eosinophils, respectively. |
| SMILES | Clc1cncc(c1NC(=O)c2cc(c(cc2)OC)OC3CCCC3)Cl |
| 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) |
| InChI Key | RRRUXBQSQLKHEL-UHFFFAOYSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 41106305 |
| Hazard Symbols | transportation |
| MSDS | msds/67452_1_144035_83_6.pdf |
| Bioactivity | Piclamilast (RP 73401) is a phosphodiesterase 4 (PDE4) inhibitor, with IC50 values of 16 nM and 2 nM in pig aorta and eosinophil soluble, respectively[1][2][3][4]. Related Catalog Research Areas >> Cancer Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE) Research Areas >> Inflammation/Immunology Target PDE4:16 nM (IC50, in pig aorta) PDE4:2 nM (IC50, in eosinophil soluble) PDE1:>100 μM (IC50) PDE2:40 μM (IC50) PDE3:>100 μM (IC50) PDE5:14 μM (IC50) In Vitro Piclamilast (RP 73401, 1 μM, 30 min) significantly inhibits the changes in 23 genes via mechanisms involving AP-1 activation and c-Jun phosphorylation at Ser63[2]. Piclamilast (RP 73401) exhibits IC50 values >100 μM, 40 μM, >100 μM, 14 μM for PDE1, PDE2, PDE3 and PDE5. Respectively[4]. RT-PCR[2] Cell Line: Human A549 type II lung epithelial cells. Concentration: 1 μM (H2O2 200 μM). Incubation Time: 30 min. Result: Prevented H2O2 -induced changes in gene expression levels in A549 cells. Cell Viability Assay[3] Cell Line: NB4 cells. Concentration: 30 μM. Incubation Time: 3 days. Result: Exerted a significant enhancing effect on the induction of STAT1 observed in ATRA-treated NB4 cells. Caused a significant increase in the number of cells expressing NBT-R activity. In Vivo Piclamilast (RP 73401, 10 mg/kg, 30 min) alone does not affect the MST of leukemia-bearing animals. Piclamilast combined with ATRA (HY-14649) significantly more effective than ATRA alone in increasing the MST (40 days; interval 34-45 days) of leukemia-bearing animals[3]. Animal Model: SCID mice[3]. Dosage: 10 mg/kg (combined with ATRA (HY-14649)). Administration: Injection daily. Result: Significantly more effective than ATRA alone in increasing the MST (40 days; interval 34-45 days) of leukemia-bearing animals. References [1]. M J Ashton, et al. Selective type IV phosphodiesterase inhibitors as antiasthmatic agents. The syntheses and biological activities of 3-(cyclopentyloxy)-4-methoxybenzamides and analogues. J Med Chem. 1994 May 27;37(11):1696-703. [2]. Manuel Mata, et al. Piclamilast inhibits the pro-apoptotic and anti-proliferative responses of A549 cells exposed to H(2)O(2) via mechanisms involving AP-1 activation. Free Radic Res. 2012 May;46(5):690-9. [3]. Edoardo Parrella, et al. Phosphodiesterase IV inhibition by piclamilast potentiates the cytodifferentiating action of retinoids in myeloid leukemia cells. Cross-talk between the cAMP and the retinoic acid signaling pathways. J Biol Chem . 2004 Oct 1;279(40):42026-40. [4]. T Ukita, et al. Novel, potent, and selective phosphodiesterase-4 inhibitors as antiasthmatic agents: synthesis and biological activities of a series of 1-pyridylnaphthalene derivatives. J Med Chem. 1999 Mar 25;42(6):1088-99. Chemical & Physical Properties Density 1.4±0.1 g/cm3 Boiling Point 447.8±45.0 °C at 760 mmHg Molecular Formula C18H18Cl2N2O3 Molecular Weight 381.253 Flash Point 224.6±28.7 °C Exact Mass 380.069458 PSA 63.68000 LogP 5.25 Vapour Pressure 0.0±1.1 mmHg at 25°C Index of Refraction 1.626 InChIKey RRRUXBQSQLKHEL-UHFFFAOYSA-N SMILES COc1ccc(C(=O)Nc2c(Cl)cncc2Cl)cc1OC1CCCC1 |
| Use of | Piclamilast (RP 73401) is a phosphodiesterase 4 (PDE4) inhibitor, with IC50 values of 16 nM and 2 nM in pig aorta and eosinophil soluble, respectively[1][2][3][4]. Properties Articles23 Name piclamilast Synonym More Synonyms Piclamilast Biological Activity Description Piclamilast (RP 73401) is a phosphodiesterase 4 (PDE4) inhibitor, with IC50 values of 16 nM and 2 nM in pig aorta and eosinophil soluble, respectively[1][2][3][4]. Related Catalog Research Areas >> Cancer Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE) Research Areas >> Inflammation/Immunology PDE4:16 nM (IC50, in pig aorta) PDE4:2 nM (IC50, in eosinophil soluble) PDE1:>100 μM (IC50) PDE2:40 μM (IC50) PDE3:>100 μM (IC50) PDE5:14 μM (IC50) References [1]. M J Ashton, et al. Selective type IV phosphodiesterase inhibitors as antiasthmatic agents. The syntheses and biological activities of 3-(cyclopentyloxy)-4-methoxybenzamides and analogues. J Med Chem. 1994 May 27;37(11):1696-703. [3]. Edoardo Parrella, et al. Phosphodiesterase IV inhibition by piclamilast potentiates the cytodifferentiating action of retinoids in myeloid leukemia cells. Cross-talk between the cAMP and the retinoic acid signaling pathways. J Biol Chem . 2004 Oct 1;279(40):42026-40. [4]. T Ukita, et al. Novel, potent, and selective phosphodiesterase-4 inhibitors as antiasthmatic agents: synthesis and biological activities of a series of 1-pyridylnaphthalene derivatives. J Med Chem. 1999 Mar 25;42(6):1088-99. Chemical & Physical Properties Exact Mass 380.069458 PSA 63.68000 Index of Refraction 1.626 InChIKey RRRUXBQSQLKHEL-UHFFFAOYSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available If applicable, the chemical meets the requirements of the Regulations on the Safety Management of Hazardous Chemicals (adopted by the State Council on January 9, 2002). |
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